Patent Grant
11094886
The entire disclosure of Japanese Patent Applications No. 2019-167636 filed Sep. 13, 2019, No. 2019-213374 filed Nov. 26, 2019, No. 2019-239596 filed Dec. 27, 2019, No. 2020-023551 filed Feb. 14, 2020, No. 2020-073060 filed Apr. 15, 2020, and No. 2020-073089 filed Apr. 15, 2020 is expressly incorporated by reference herein.
The present invention relates to an organic electroluminescence device and an electronic device.
An organic electroluminescence device (hereinafter, occasionally referred to as “organic EL device”) has found its application in a full-color display for mobile phones, televisions and the like. When a voltage is applied to an organic EL device, holes and electrons are injected from an anode and a cathode, respectively, into an emitting layer. The injected electrons and holes are recombined in the emitting layer to form excitons. Specifically, according to the electron spin statistics theory, singlet excitons and triplet excitons are generated at a ratio of 25%:75%.
Various studies have been made for compounds to be used for the organic EL device in order to enhance the performance of the organic EL device (see, for instance, Patent Literature 1: JP 2013-157552 A, Patent Literature 2: WO 2004/018587 A, Patent Literature 3: WO 2005/115950 A, Patent Literature 4: WO 2011/077691 A, Patent Literature 5: JP 2018-125504 A, and Patent Literature 6: US 2019/280209 A). The performance of the organic EL device is evaluatable in terms of, for instance, luminance, emission wavelength, chromaticity, emission efficiency, drive voltage, and lifetime.
An object of the invention is to provide an organic electroluminescence device with enhanced performance. Another object of the invention is to provide an organic electroluminescence device with enhanced luminous efficiency and an electronic device including the organic electroluminescence device.
Provided according to an aspect of the invention is an organic electroluminescence device including an anode, a cathode, a first emitting layer disposed between the anode and the cathode, and a second emitting layer disposed between the first emitting layer and the cathode, the first emitting layer containing a first host material in a form of a first compound containing at least one group represented by a formula (11) below, the first compound being represented by a formula (1) below, the second emitting layer containing a second host material in a form of a second compound represented by a formula (2) below, the first emitting layer and the second emitting layer being in direct contact with each other.
In the formula (1): R101 to R110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (11);
at least one of R101 to R110 is a group represented by the formula (11); when the group represented by the formula (11) is present in plural, the plurality of groups represented by the formula (11) are mutually the same or different;
L101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
Ar101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
mx is 0, 1, 2, 3, 4, or 5;
when two or more L101 are present, the two or more L101 are mutually the same or different;
when two or more Ar101 are present, the two or more Ar101 are mutually the same or different; and
* in the formula (11) represents a bonding position to the pyrene ring in the formula (1).
In the formula (2): R201 to R208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L201 and L202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and
Ar201 and Ar202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the first compound represented by the formula (1) and the second compound represented by the formula (2): R901, R902, R903, R904, R905, R906, R907, R801, and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R906 are present, the plurality of R906 are mutually the same or different;
when a plurality of R907 are present, the plurality of R907 are mutually the same or different;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different; and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different.
Provided according to another aspect of the invention is an organic electroluminescence device including an anode, a cathode, a first emitting layer disposed between the anode and the cathode, and a second emitting layer disposed between the first emitting layer and the cathode, the first emitting layer containing a first host material in a form of a first compound represented by a formula (101) below, the second emitting layer containing the second host material in a form of the second compound represented by the formula (2), the first emitting layer and the second emitting layer being in direct contact with each other.
In the formula (101): R101 to R110, and R111 to R120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
one of R101 to R110 represents a bonding position to L101, one of R111 to R120 represents a bonding position to L101;
L101 is a divalent group derived by removing one hydrogen atom from an aryl ring of a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group or a substituted or unsubstituted 2-naphthyl group;
mx is 1, 2, or 3; and
when two or more L101 are present, the two or more L101 are mutually the same or different.
According to still another aspect of the invention, an electronic device including the organic electroluminescence device according to the above aspect of the invention is provided.
According to the above aspect of the invention, an organic electroluminescence device with enhanced performance can be provided. In addition, according to the above aspect of the invention, an organic electroluminescence device with enhanced luminous efficiency can be provided. According to the further aspect of the invention, an electronic device installed with the organic electroluminescence device can be provided.
A FIGURE schematically illustrates an arrangement of an exemplary organic electroluminescence device according to an exemplary embodiment of the invention.
Herein, a hydrogen atom includes isotope having different numbers of neutrons, specifically, protium, deuterium and tritium.
In chemical formulae herein, it is assumed that a hydrogen atom (i.e. protium, deuterium and tritium) is bonded to each of bondable positions that are not annexed with signs “R” or the like or “D” representing a protium.
Herein, the ring carbon atoms refer to the number of carbon atoms among atoms forming a ring of a compound (e.g., a monocyclic compound, fused-ring compound, crosslinking compound, carbon ring compound, and heterocyclic compound) in which the atoms are bonded with each other to form the ring. When the ring is substituted by a substituent(s), carbon atom(s) contained in the substituent(s) is not counted in the ring carbon atoms. Unless otherwise specified, the same applies to the “ring carbon atoms” described later. For instance, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for instance, 9,9-diphenylfluorenyl group has 13 ring carbon atoms and 9,9′-spirobifluorenyl group has 25 ring carbon atoms.
When a benzene ring is substituted by a substituent in a form of, for instance, an alkyl group, the number of carbon atoms of the alkyl group is not counted in the number of the ring carbon atoms of the benzene ring. Accordingly, the benzene ring substituted by an alkyl group has 6 ring carbon atoms. When a naphthalene ring is substituted by a substituent in a form of, for instance, an alkyl group, the number of carbon atoms of the alkyl group is not counted in the number of the ring carbon atoms of the naphthalene ring. Accordingly, the naphthalene ring substituted by an alkyl group has 10 ring carbon atoms.
Herein, the ring atoms refer to the number of atoms forming a ring of a compound (e.g., a monocyclic compound, fused-ring compound, crosslinking compound, carbon ring compound, and heterocyclic compound) in which the atoms are bonded to each other to form the ring (e.g., monocyclic ring, fused ring, and ring assembly). Atom(s) not forming the ring (e.g., hydrogen atom(s) for saturating the valence of the atom which forms the ring) and atom(s) in a substituent by which the ring is substituted are not counted as the ring atoms. Unless otherwise specified, the same applies to the “ring atoms” described later. For instance, a pyridine ring has 6 ring atoms, a quinazoline ring has 10 ring atoms, and a furan ring has 5 ring atoms. For instance, the number of hydrogen atom(s) bonded to a pyridine ring or the number of atoms forming a substituent are not counted as the pyridine ring atoms. Accordingly, a pyridine ring bonded with a hydrogen atom(s) or a substituent(s) has 6 ring atoms. For instance, the hydrogen atom(s) bonded to a quinazoline ring or the atoms forming a substituent are not counted as the quinazoline ring atoms. Accordingly, a quinazoline ring bonded with hydrogen atom(s) or a substituent(s) has 10 ring atoms.
Herein, “XX to YY carbon atoms” in the description of “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represent carbon atoms of an unsubstituted ZZ group and do not include carbon atoms of a substituent(s) of the substituted ZZ group. Herein, “YY” is larger than “XX,” “XX” representing an integer of 1 or more and “YY” representing an integer of 2 or more.
Herein, “XX to YY atoms” in the description of “substituted or unsubstituted ZZ group having XX to YY atoms” represent atoms of an unsubstituted ZZ group and does not include atoms of a substituent(s) of the substituted ZZ group. Herein, “YY” is larger than “XX,” “XX” representing an integer of 1 or more and “YY” representing an integer of 2 or more.
Herein, an unsubstituted ZZ group refers to an “unsubstituted ZZ group” in a “substituted or unsubstituted ZZ group,” and a substituted ZZ group refers to a “substituted ZZ group” in a “substituted or unsubstituted ZZ group.”
Herein, the term “unsubstituted” used in a “substituted or unsubstituted ZZ group” means that a hydrogen atom(s) in the ZZ group is not substituted with a substituent(s). The hydrogen atom(s) in the “unsubstituted ZZ group” is protium, deuterium, or tritium.
Herein, the term “substituted” used in a “substituted or unsubstituted ZZ group” means that at least one hydrogen atom in the ZZ group is substituted with a substituent. Similarly, the term “substituted” used in a “BB group substituted by AA group” means that at least one hydrogen atom in the BB group is substituted with the AA group.
Substituent Mentioned Herein
Substituents mentioned herein will be described below.
An “unsubstituted aryl group” mentioned herein has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
An “unsubstituted heterocyclic group” mentioned herein has, unless otherwise specified herein, 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring atoms.
An “unsubstituted alkyl group” mentioned herein has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
An “unsubstituted alkenyl group” mentioned herein has, unless otherwise specified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6 carbon atoms.
An “unsubstituted alkynyl group” mentioned herein has, unless otherwise specified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6 carbon atoms.
An “unsubstituted cycloalkyl group” mentioned herein has, unless otherwise specified herein, 3 to 50, preferably 3 to 20, more preferably 3 to 6 ring carbon atoms.
An “unsubstituted arylene group” mentioned herein has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
An “unsubstituted divalent heterocyclic group” mentioned herein has, unless otherwise specified herein, 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring atoms.
An “unsubstituted alkylene group” mentioned herein has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
Substituted or Unsubstituted Aryl Group
Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” mentioned herein include unsubstituted aryl groups (specific example group G1A) below and substituted aryl groups (specific example group G1B) (Herein, an unsubstituted aryl group refers to an “unsubstituted aryl group” in a “substituted or unsubstituted aryl group,” and a substituted aryl group refers to a “substituted aryl group” in a “substituted or unsubstituted aryl group.”) A simply termed “aryl group” herein includes both of “unsubstituted aryl group” and “substituted aryl group.”
The “substituted aryl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted aryl group” with a substituent. Examples of the “substituted aryl group” include a group derived by substituting at least one hydrogen atom in the “unsubstituted aryl group” in the specific example group G1A below with a substituent, and examples of the substituted aryl group in the specific example group G1B below. It should be noted that the examples of the “unsubstituted aryl group” and the “substituted aryl group” mentioned herein are merely exemplary, and the “substituted aryl group” mentioned herein includes a group derived by substituting a hydrogen atom bonded to a carbon atom of a skeleton of a “substituted aryl group” in the specific example group G1B below, and a group derived by substituting a hydrogen atom of a substituent of the “substituted aryl group” in the specific example group G1B below.
Unsubstituted Aryl Group (Specific Example Group G1A):
a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from cyclic structures represented by formulae (TEMP-1) to (TEMP-15) below.
Substituted Aryl Group (Specific Example Group G1B):
o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and a group derived by substituting at least one hydrogen atom of a monovalent group derived from one of the cyclic structures represented by the formulae (TEMP-1) to (TEMP-15) with a substituent.
Substituted or Unsubstituted Heterocyclic Group
The “heterocyclic group” mentioned herein refers to a cyclic group having at least one hetero atom in the ring atoms. Specific examples of the hetero atom include a nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
The “heterocyclic group” mentioned herein is a monocyclic group or a fused-ring group.
The “heterocyclic group” mentioned herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples (specific example group G2) of the “substituted or unsubstituted heterocyclic group” mentioned herein include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) (Herein, an unsubstituted heterocyclic group refers to an “unsubstituted heterocyclic group” in a “substituted or unsubstituted heterocyclic group,” and a substituted heterocyclic group refers to a “substituted heterocyclic group” in a “substituted or unsubstituted heterocyclic group.”) A simply termed “heterocyclic group” herein includes both of “unsubstituted heterocyclic group” and “substituted heterocyclic group.”
The “substituted heterocyclic group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted heterocyclic group” with a substituent. Specific examples of the “substituted heterocyclic group” include a group derived by substituting at least one hydrogen atom in the “unsubstituted heterocyclic group” in the specific example group G2A below with a substituent, and examples of the substituted heterocyclic group in the specific example group G2B below. It should be noted that the examples of the “unsubstituted heterocyclic group” and the “substituted heterocyclic group” mentioned herein are merely exemplary, and the “substituted heterocyclic group” mentioned herein includes a group derived by substituting a hydrogen atom bonded to a ring atom of a skeleton of a “substituted heterocyclic group” in the specific example group G2B below, and a group derived by substituting a hydrogen atom of a substituent of the “substituted heterocyclic group” in the specific example group G2B below.
The specific example group G2A includes, for instance, unsubstituted heterocyclic groups including a nitrogen atom (specific example group G2A1) below, unsubstituted heterocyclic groups including an oxygen atom (specific example group G2A2) below, unsubstituted heterocyclic groups including a sulfur atom (specific example group G2A3) below, and monovalent heterocyclic groups (specific example group G2A4) derived by removing a hydrogen atom from cyclic structures represented by formulae (TEMP-16) to (TEMP-33) below.
The specific example group G2B includes, for instance, substituted heterocyclic groups including a nitrogen atom (specific example group G2B1) below, substituted heterocyclic groups including an oxygen atom (specific example group G2B2) below, substituted heterocyclic groups including a sulfur atom (specific example group G2B3) below, and groups derived by substituting at least one hydrogen atom of the monovalent heterocyclic groups (specific example group G2B4) derived from the cyclic structures represented by formulae (TEMP-16) to (TEMP-33) below.
Unsubstituted Heterocyclic Groups Including Nitrogen Atom (Specific Example Group G2A1):
pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, a pyridyl group, pyridazynyl group, a pyrimidinyl group, pyrazinyl group, a triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolizinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenanthridinyl group, acridinyl group, phenazinyl group, carbazolyl group, benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.
Unsubstituted Heterocyclic Groups Including Oxygen Atom (Specific Example Group G2A2):
furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
Unsubstituted Heterocyclic Groups Including Sulfur Atom (Specific Example Group G2A3):
thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (nahthobenzothienyl group), benzothiazolyl group, benzisothiazolyl group, phenothiazinyl group, dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
Monovalent Heterocyclic Groups Derived by Removing a Hydrogen Atom from Cyclic Structures Represented by Formulae (TEMP-16) to (TEMP-33) Below (Specific Example Group G2A4):
In the formulae (TEMP-16) to (TEMP-33), XA and YA are each independently an oxygen atom, a sulfur atom, NH or CH2, with a proviso that at least one of XA and YA is an oxygen atom, a sulfur atom, or NH.
When at least one of XA and YA in the formulae (TEMP-16) to (TEMP-33) is NH or CH2, the monovalent heterocyclic groups derived from the cyclic structures represented by the formulae (TEMP-16) to (TEMP-33) include a monovalent group derived by removing one hydrogen atom from NH or CH2.
Substituted Heterocyclic Groups Including Nitrogen Atom (Specific Example Group G2B1):
(9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylylquinazolinyl group.
Substituted Heterocyclic Groups Including Oxygen Atom (Specific Example Group G2B2):
phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
Substituted Heterocyclic Groups Including Sulfur Atom (Specific Example Group G2B3):
phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
Groups Derived by Substituting at Least One Hydrogen Atom of Monovalent Heterocyclic Group Derived from Cyclic Structures Represented by Formulae (TEMP-16) to (TEMP-33) with Substituent (Specific Example Group G2B4):
The “at least one hydrogen atom of a monovalent heterocyclic group” means at least one hydrogen atom selected from a hydrogen atom bonded to a ring carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom of at least one of XA or YA in a form of NH, and a hydrogen atom of one of XA and YA in a form of a methylene group (CH2).
Substituted or Unsubstituted Alkyl Group Specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” mentioned herein include unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B below) (Herein, an unsubstituted alkyl group refers to an “unsubstituted alkyl group” in a “substituted or unsubstituted alkyl group,” and a substituted alkyl group refers to a “substituted alkyl group” in a “substituted or unsubstituted alkyl group.”) A simply termed “alkyl group” herein includes both of “unsubstituted alkyl group” and “substituted alkyl group.”
The “substituted alkyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkyl group” with a substituent. Specific examples of the “substituted alkyl group” include a group derived by substituting at least one hydrogen atom of an “unsubstituted alkyl group” (specific example group G3A) below with a substituent, and examples of the substituted alkyl group (specific example group G3B) below. Herein, the alkyl group for the “unsubstituted alkyl group” refers to a chain alkyl group. Accordingly, the “unsubstituted alkyl group” include linear “unsubstituted alkyl group” and branched “unsubstituted alkyl group.” It should be noted that the examples of the “unsubstituted alkyl group” and the “substituted alkyl group” mentioned herein are merely exemplary, and the “substituted alkyl group” mentioned herein includes a group derived by substituting a hydrogen atom bonded to a carbon atom of a skeleton of the “substituted alkyl group” in the specific example group G3B, and a group derived by substituting a hydrogen atom of a substituent of the “substituted alkyl group” in the specific example group G3B.
Unsubstituted Alkyl Group (Specific Example Group G3A):
methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
Substituted Alkyl Group (Specific Example Group G3B):
heptafluoropropyl group (including isomer thereof), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.
Substituted or Unsubstituted Alkenyl Group
Specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” mentioned herein include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B) (Herein, an unsubstituted alkenyl group refers to an “unsubstituted alkenyl group” in a “substituted or unsubstituted alkenyl group,” and a substituted alkenyl group refers to a “substituted alkenyl group” in a “substituted or unsubstituted alkenyl group.”) A simply termed “alkenyl group” herein includes both of “unsubstituted alkenyl group” and “substituted alkenyl group.”
The “substituted alkenyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkenyl group” with a substituent. Specific examples of the “substituted alkenyl group” include an “unsubstituted alkenyl group” (specific example group G4A) substituted by a substituent, and examples of the substituted alkenyl group (specific example group G4B) below. It should be noted that the examples of the “unsubstituted alkenyl group” and the “substituted alkenyl group” mentioned herein are merely exemplary, and the “substituted alkenyl group” mentioned herein includes a group derived by substituting a hydrogen atom of a skeleton of the “substituted alkenyl group” in the specific example group G4B with a substituent, and a group derived by substituting a hydrogen atom of a substituent of the “substituted alkenyl group” in the specific example group G4B with a substituent.
Unsubstituted Alkenyl Group (Specific Example Group G4A):
vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
Substituted Alkenyl Group (Specific Example Group G4B):
1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
Substituted or Unsubstituted Alkynyl Group
Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” mentioned herein include unsubstituted alkynyl groups (specific example group G5A) below (Herein, an unsubstituted alkynyl group refers to an “unsubstituted alkynyl group” in the “substituted or unsubstituted alkynyl group.”) A simply termed “alkynyl group” herein includes both of “unsubstituted alkynyl group” and “substituted alkynyl group.”
The “substituted alkynyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkynyl group” with a substituent. Specific examples of the “substituted alkynyl group” include a group derived by substituting at least one hydrogen atom of the “unsubstituted alkynyl group” (specific example group G5A) below with a substituent.
Unsubstituted Alkynyl Group (Specific Example Group G5A): ethynyl group
Substituted or Unsubstituted Cycloalkyl Group
Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” mentioned herein include unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B) (Herein, an unsubstituted cycloalkyl group refers to an “unsubstituted cycloalkyl group” in the “substituted or unsubstituted cycloalkyl group,” and a substituted cycloalkyl group refers to the “substituted cycloalkyl group” in a “substituted or unsubstituted cycloalkyl group.”) A simply termed “cycloalkyl group” herein includes both of “unsubstituted cycloalkyl group” and “substituted cycloalkyl group.”
The “substituted cycloalkyl group” refers to a group derived by substituting at least one hydrogen atom of an “unsubstituted cycloalkyl group” with a substituent. Specific examples of the “substituted cycloalkyl group” include a group derived by substituting at least one hydrogen atom of the “unsubstituted cycloalkyl group” (specific example group G6A) below with a substituent, and examples of the substituted cycloalkyl group (specific example group G6B) below. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group” mentioned herein are merely exemplary, and the “substituted cycloalkyl group” mentioned herein includes a group derived by substituting at least one hydrogen atom bonded to a carbon atom of a skeleton of the “substituted cycloalkyl group” in the specific example group G6B with a substituent, and a group derived by substituting a hydrogen atom of a substituent of the “substituted cycloalkyl group” in the specific example group G6B with a substituent.
Unsubstituted Cycloalkyl Group (Specific Example Group G6A):
cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
Substituted Cycloalkyl Group (Specific Example Group G6B):
4-methylcyclohexyl group.
Group Represented by “—Si(R901)(R902)(R903)”
Specific examples (specific example group G7) of the group represented herein by —Si(R901)(R902)(R903) include:
—Si(G1)(G1)(G1);
—Si(G1)(G2)(G2);
—Si(G1)(G1)(G2);
—Si(G2)(G2)(G2);
—Si(G3)(G3)(G3); and
—Si(G6)(G6)(G6),
where:
G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3;
G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6;
the plurality of G1 in —Si(G1)(G1)(G1) are mutually the same or different;
the plurality of G2 in —Si(G1)(G2)(G2) are mutually the same or different;
the plurality of G1 in —Si(G1)(G1)(G2) are mutually the same or different;
the plurality of G2 in —Si(G2)(G2)(G2) are mutually the same or different;
The plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different;
the plurality of G6 in —Si(G6)(G6)(G6) are mutually the same or different. Group Represented by “—O—(R904)”
Specific examples (specific example group G8) of a group represented by —O—(R904) herein include
—O(G1);
—O(G2);
—O(G3); and
—O(G6) where:
G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3; and
G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6.
Group Represented by “—S—(R905)”
Specific examples (specific example group G9) of a group represented herein by —S—(R905) include:
—S(G1);
—S(G2);
—S(G3); and
—S(G6)
where:
G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3; and
G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6.
Group Represented by “—N(R906)(R907)”
Specific examples (specific example group G10) of a group represented herein by —N(R906)(R907) include:
—N(G1)(G1);
—N(G2)(G2);
—N(G1)(G2);
—N(G3)(G3); and
—N(G6)(G6)
where:
G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3;
G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6;
the plurality of G1 in —N(G1)(G1) are mutually the same or different;
the plurality of G2 in —N(G2)(G2) are mutually the same or different;
the plurality of G3 in —N(G3)(G3) are mutually the same or different; and
the plurality of G6 in —N(G6)(G6) are mutually the same or different.
Halogen Atom
Specific examples (specific example group G11) of “halogen atom” mentioned herein include a fluorine atom, chlorine atom, bromine atom, and iodine atom.
Substituted or Unsubstituted Fluoroalkyl Group
The “substituted or unsubstituted fluoroalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom of the “substituted or unsubstituted alkyl group” with a fluorine atom, and also includes a group (perfluoro group) derived by substituting all of the hydrogen atoms bonded to a carbon atom(s) of the alkyl group in the “substituted or unsubstituted alkyl group” with fluorine atoms. An “unsubstituted fluoroalkyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms. The “substituted fluoroalkyl group” refers to a group derived by substituting at least one hydrogen atom in a “fluoroalkyl group” with a substituent. It should be noted that the examples of the “substituted fluoroalkyl group” mentioned herein includes a group derived by substituting at least one hydrogen atom bonded to a carbon atom of an alkyl chain of a “substituted fluoroalkyl group” with a substituent, and a group derived by substituting at least one hydrogen atom of a substituent of the “substituted fluoroalkyl group” with a substituent. Specific examples of the “substituted fluoroalkyl group” include a group derived by substituting at least one hydrogen atom of the “alkyl group” (specific example group G3) with a fluorine atom.
Substituted or Unsubstituted Haloalkyl Group
The “substituted or unsubstituted haloalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom of the “substituted or unsubstituted alkyl group” with a halogen atom, and also includes a group derived by substituting all of the hydrogen atoms bonded to a carbon atom(s) of the alkyl group in the “substituted or unsubstituted alkyl group” with halogen atoms. An “unsubstituted haloalkyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms. The “substituted haloalkyl group” refers to a group derived by substituting at least one hydrogen atom in a “haloalkyl group” with a substituent. It should be noted that the examples of the “substituted haloalkyl group” mentioned herein includes a group derived by substituting at least one hydrogen atom bonded to a carbon atom of an alkyl chain of a “substituted haloalkyl group” with a substituent, and a group derived by substituting at least one hydrogen atom of a substituent of the “substituted haloalkyl group” with a substituent. Specific examples of the “substituted haloalkyl group” include a group derived by substituting at least one hydrogen atom of the “alkyl group” (specific example group G3) with a halogen atom. The haloalkyl group is sometimes referred to as a halogenated alkyl group.
Substituted or Unsubstituted Alkoxy Group
Specific examples of a “substituted or unsubstituted alkoxy group” mentioned herein include a group represented by —O(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. An “unsubstituted alkoxy group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms.
Substituted or Unsubstituted Alkylthio Group
Specific examples of a “substituted or unsubstituted alkylthio group” mentioned herein include a group represented by —S(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. An “unsubstituted alkylthio group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms.
Substituted or Unsubstituted Aryloxy Group
Specific examples of a “substituted or unsubstituted aryloxy group” mentioned herein include a group represented by —O(G1), G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. An “unsubstituted aryloxy group” has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
Substituted or Unsubstituted Arylthio Group
Specific examples of a “substituted or unsubstituted arylthio group” mentioned herein include a group represented by —S(G1), G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. An “unsubstituted arylthio group” has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
Substituted or Unsubstituted Trialkylsilyl Group
Specific examples of a “trialkylsilyl group” mentioned herein include a group represented by —Si(G3)(G3)(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. The plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different. Each of the alkyl groups in the “trialkylsilyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
Substituted or Unsubstituted Aralkyl Group
Specific examples of a “substituted or unsubstituted aralkyl group” mentioned herein include a group represented by (G3)-(G1), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3, G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. Accordingly, the “aralkyl group” is a group derived by substituting a hydrogen atom of the “alkyl group” with a substituent in a form of the “aryl group,” which is an example of the “substituted alkyl group.” An “unsubstituted aralkyl group,” which is an “unsubstituted alkyl group” substituted by an “unsubstituted aryl group,” has, unless otherwise specified herein, 7 to 50 carbon atoms, preferably 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms.
Specific examples of the “substituted or unsubstituted aralkyl group” include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
Preferable examples of the substituted or unsubstituted aryl group mentioned herein include, unless otherwise specified herein, a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.
Preferable examples of the substituted or unsubstituted heterocyclic group mentioned herein include, unless otherwise specified herein, a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
The carbazolyl group mentioned herein is, unless otherwise specified herein, specifically a group represented by one of formulae below.
The (9-phenyl)carbazolyl group mentioned herein is, unless otherwise specified herein, specifically a group represented by one of formulae below.
In the formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
The dibenzofuranyl group and dibenzothiophenyl group mentioned herein are, unless otherwise specified herein, each specifically represented by one of formulae below.
In the formulae (TEMP-34) to (TEMP-41), * represents a bonding position.
Preferable examples of the substituted or unsubstituted alkyl group mentioned herein include, unless otherwise specified herein, a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t-butyl group.
Substituted or Unsubstituted Arylene Group
The “substituted or unsubstituted arylene group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on an aryl ring of the “substituted or unsubstituted aryl group.” Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include a divalent group derived by removing one hydrogen atom on an aryl ring of the “substituted or unsubstituted aryl group” in the specific example group G1.
Substituted or Unsubstituted Divalent Heterocyclic Group
The “substituted or unsubstituted divalent heterocyclic group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on a heterocycle of the “substituted or unsubstituted heterocyclic group.” Specific examples of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13) include a divalent group derived by removing one hydrogen atom on a heterocyclic ring of the “substituted or unsubstituted heterocyclic group” in the specific example group G2.
Substituted or Unsubstituted Alkylene Group
The “substituted or unsubstituted alkylene group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on an alkyl chain of the “substituted or unsubstituted alkyl group.” Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include a divalent group derived by removing one hydrogen atom on an alkyl chain of the “substituted or unsubstituted alkyl group” in the specific example group G3.
The substituted or unsubstituted arylene group mentioned herein is, unless otherwise specified herein, preferably any one of groups represented by formulae (TEMP-42) to (TEMP-68) below.
In the formulae (TEMP-42) to (TEMP-52), Q1 to Q10 each independently are a hydrogen atom or a substituent.
In the formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
In the formulae (TEMP-53) to (TEMP-62), Q1 to Q10 each independently are a hydrogen atom or a substituent.
In the formulae, Q9 and Q10 may be mutually bonded through a single bond to form a ring.
In the formulae (TEMP-53) to (TEMP-62), * represents a bonding position.
In the formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently are a hydrogen atom or a substituent.
In the formulae (TEMP-63) to (TEMP-68), * represents a bonding position.
The substituted or unsubstituted divalent heterocyclic group mentioned herein is, unless otherwise specified herein, preferably a group represented by any one of formulae (TEMP-69) to (TEMP-102) below.
In the formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently are a hydrogen atom or a substituent.
In the formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently are a hydrogen atom or a substituent.
The substituent mentioned herein has been described above.
Instance “Bonded to Form a Ring”
Instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded” mentioned herein refer to instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring, “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring,” and “at least one combination of adjacent two or more (of . . . ) are not mutually bonded.”
Instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring” and “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring” mentioned herein (these instances will be sometimes collectively referred to as an instance “bonded to form a ring” hereinafter) will be described below. An anthracene compound having a basic skeleton in a form of an anthracene ring and represented by a formula (TEMP-103) below will be used as an example for the description.
For instance, when “at least one combination of adjacent two or more of” R921 to R930 “are mutually bonded to form a ring,” the pair of adjacent ones of R921 to R930 (i.e. the combination at issue) is a pair of R921 and a pair of R922, R922 and R923, a pair of R923 and R924, a pair of R924 and R930, a pair of R930 and R925, a pair of R925 and R926, a pair of R926 and R927, a pair of R927 and R928, a pair of R928 and R929, or a pair of R929 and R921.
The term “at least one combination” means that two or more of the above combinations of adjacent two or more of R921 to R930 may simultaneously form rings. For instance, when R921 and R922 are mutually bonded to form a ring QA and R925 and R926 are simultaneously mutually bonded to form a ring QB, the anthracene compound represented by the formula (TEMP-103) is represented by a formula (TEMP-104) below.
The instance where the “combination of adjacent two or more” form a ring means not only an instance where the “two” adjacent components are bonded but also an instance where adjacent “three or more” are bonded. For instance, R921 and R922 are mutually bonded to form a ring QA and R922, R923 are mutually bonded to form a ring QC, and mutually adjacent three components (R921, R922 and R923) are mutually bonded to form a ring fused to the anthracene basic skeleton. In this case, the anthracene compound represented by the formula (TEMP-103) is represented by a formula (TEMP-105) below. In the formula (TEMP-105) below, the ring QA and the ring QC share R922.
The formed “monocyclic ring” or “fused ring” may be, in terms of the formed ring in itself, a saturated ring or an unsaturated ring. When the “combination of adjacent two” form a “monocyclic ring” or a “fused ring,” the “monocyclic ring” or “fused ring” may be a saturated ring or an unsaturated ring. For instance, the ring QA and the ring QB formed in the formulae (TEMP-104) and (TEMP-105) are each independently a “monocyclic ring” or a “fused ring.” Further, the ring QA and the ring QC formed in the formula (TEMP-105) are each a “fused ring.” The ring QA and the ring QC in the formula (TEMP-105) are fused to form a fused ring. When the ring QA in the formula (TEMP-104) is a benzene ring, the ring QA is a monocyclic ring. When the ring QA in the formula (TEMP-104) is a naphthalene ring, the ring QA is a fused ring.
The “unsaturated ring” represents an aromatic hydrocarbon ring or an aromatic heterocycle. The “saturated ring” represents an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
Specific examples of the aromatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G1 with a hydrogen atom.
Specific examples of the aromatic heterocycle include a ring formed by terminating a bond of an aromatic heterocyclic group in the specific example of the specific example group G2 with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G6 with a hydrogen atom.
The phrase “to form a ring” herein means that a ring is formed only by a plurality of atoms of a basic skeleton, or by a combination of a plurality of atoms of the basic skeleton and one or more optional atoms. For instance, the ring QA formed by mutually bonding R921 and R922 shown in the formula (TEMP-104) is a ring formed by a carbon atom of the anthracene skeleton bonded with R921, a carbon atom of the anthracene skeleton bonded with R922, and one or more optional atoms. Specifically, when the ring QA is a monocyclic unsaturated ring formed by R921 and R922, the ring formed by a carbon atom of the anthracene skeleton bonded with R921, a carbon atom of the anthracene skeleton bonded with R922, and four carbon atoms is a benzene ring.
The “optional atom” is, unless otherwise specified herein, preferably at least one atom selected from the group consisting of a carbon atom, nitrogen atom, oxygen atom, and sulfur atom. A bond of the optional atom (e.g. a carbon atom and a nitrogen atom) not forming a ring may be terminated by a hydrogen atom or the like or may be substituted by an “optional substituent” described later. When the ring includes an optional element other than carbon atom, the resultant ring is a heterocycle.
The number of “one or more optional atoms” forming the monocyclic ring or fused ring is, unless otherwise specified herein, preferably in a range from 2 to 15, more preferably in a range from 3 to 12, further preferably in a range from 3 to 5.
Unless otherwise specified herein, the ring, which may be a “monocyclic ring” or “fused ring,” is preferably a “monocyclic ring.”
Unless otherwise specified herein, the ring, which may be a “saturated ring” or “unsaturated ring,” is preferably an “unsaturated ring.”
Unless otherwise specified herein, the “monocyclic ring” is preferably a benzene ring.
Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring.
When “at least one combination of adjacent two or more” (of . . . ) are “mutually bonded to form a substituted or unsubstituted monocyclic ring” or “mutually bonded to form a substituted or unsubstituted fused ring,” unless otherwise specified herein, at least one combination of adjacent two or more of components are preferably mutually bonded to form a substituted or unsubstituted “unsaturated ring” formed of a plurality of atoms of the basic skeleton, and 1 to 15 atoms of at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
When the “monocyclic ring” or the “fused ring” has a substituent, the substituent is the substituent described in later-described “optional substituent.” When the “monocyclic ring” or the “fused ring” has a substituent, specific examples of the substituent are the substituents described in the above under the subtitle “Substituent Mentioned Herein.”
When the “saturated ring” or the “unsaturated ring” has a substituent, the substituent is the substituent described in later-described “optional substituent.” When the “monocyclic ring” or the “fused ring” has a substituent, specific examples of the substituent are the substituents described in the above under the subtitle “Substituent Mentioned Herein.”
The above is the description for the instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring” and “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring” mentioned herein (sometimes referred to as an instance “bonded to form a ring”.
Substituent Meant by “Substituted or Unsubstituted”
In an exemplary embodiment herein, the substituent meant by the phrase “substituted or unsubstituted” (sometimes referred to as an “optional substituent” hereinafter) is, for instance, a group selected from the group consisting of an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms; R901 to R907 each independently are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when two or more R901 are present, the two or more R901 are mutually the same or different;
when two or more R902 are present, the two or more R902 are mutually the same or different;
when two or more R903 are present, the two or more R903 are mutually the same or different;
when two or more R904 are present, the two or more R904 are mutually the same or different;
when two or more R905 are present, the two or more R905 are mutually the same or different;
When two or more R906 are present, the two or more R906 are mutually the same or different; and
When two or more R907 are present, the two or more R907 are mutually the same or different.
In an exemplary embodiment, the substituent meant by “substituted or unsubstituted” is selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, the substituent meant by “substituted or unsubstituted” is selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.
Specific examples of the above optional substituent are the same as the specific examples of the substituent described in the above under the subtitle “Substituent Mentioned Herein.”
Unless otherwise specified herein, adjacent ones of the optional substituents may form a “saturated ring” or an “unsaturated ring,” preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted saturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.
Unless otherwise specified herein, the optional substituent may further include a substituent. Examples of the substituent for the optional substituent are the same as the examples of the optional substituent.
Herein, numerical ranges represented by “AA to BB” represents a range whose lower limit is the value (AA) recited before “to” and whose upper limit is the value (BB) recited after “to.”
Organic Electroluminescence Device
An organic electroluminescence device according to the present exemplary embodiment includes an anode, a cathode, a first emitting layer disposed between the anode and the cathode, and a second emitting layer disposed between the first emitting layer and the cathode. The first emitting layer contains a first host material in a form of a first compound including at least one group represented by a formula (11) below, the first compound being represented by a formula (1) below. The second emitting layer contains a second host material in a form of a second compound represented by a formula (2) below. In the organic EL device according to the present exemplary embodiment, the first emitting layer and the second emitting layer are in direct contact with each other.
Herein, the “host material” refers to, for instance, a material that accounts for “50 mass % or more of the layer.” Accordingly, for instance, the first emitting layer contains 50 mass % or more first compound represented by the formula (1) below with respect to a total mass of the first emitting layer. The second emitting layer contains 50 mass % or more second compound represented by the formula (2) below with respect to a total mass of the second emitting layer.
Emission Wavelength of Organic EL Device
It is preferable that the organic electroluminescence device according to the present exemplary embodiment emits, when being driven, light whose main peak wavelength ranges from 430 nm to 480 nm.
The main peak wavelength of the light emitted when the organic EL device is driven is measured as follows. Voltage is applied on the organic EL devices such that a current density becomes 10 mA/cm2, where spectral radiance spectrum is measured by a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). A peak wavelength of an emission spectrum, at which the luminous intensity of the resultant spectral radiance spectrum is at the maximum, is measured and defined as the main peak wavelength (unit: nm).
The organic EL device according to the present exemplary embodiment may include one or more organic layer in addition to the first emitting layer and the second emitting layer. Examples of the organic layer include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an emitting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, and an electron blocking layer.
The organic layer in the organic EL device according to the present exemplary embodiment, which may consist solely of the first emitting layer and the second emitting layer, may further include, for instance, at least one layer selected from the group consisting of the hole injecting layer, the hole transporting layer, the electron injecting layer, the electron transporting layer, the hole blocking layer, the electron blocking layer, and the like.
Hole Transporting Layer
The organic EL device according to the present exemplary embodiment preferably includes a hole transporting layer between the anode and the first emitting layer.
The organic EL device according to the present exemplary embodiment preferably includes an electron transporting layer between the cathode and the second emitting layer.
An exemplary structure of the organic EL device of the present exemplary embodiment is schematically shown in the FIGURE.
An organic EL device 1 includes a light-transmissive substrate 2, an anode 3, a cathode 4, and an organic layer 10 provided between the anode 3 and the cathode 4. The organic layer 10 includes a hole injecting layer 6, a hole transporting layer 7, a first emitting layer 51, a second emitting layer 52, an electron transporting layer 8, and an electron injecting layer 9, these layers being layered in this order from the anode 3.
First Compound
The first compound of the organic EL device according to the present exemplary embodiment is represented by the formula (1) below.
In the formula (1): R101 to R110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (11);
at least one of R101 to R110 is a group represented by the formula (11);
when the group represented by the formula (11) is present in plural, the plurality of groups represented by the formula (11) are mutually the same or different;
L101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
Ar101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
mx is 0, 1, 2, 3, 4, or 5;
when two or more L101 are present, the two or more L101 are mutually the same or different;
when two or more Ar101 are present, the two or more Ar101 are mutually the same or different; and
* in the formula (11) represents a bonding position to the pyrene ring in the formula (1).
In the first compound according to the present exemplary embodiment: R901, R902, R903, R904, R905, R906, R907, R801, and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R906 are present, the plurality of R906 are mutually the same or different;
when a plurality of R907 are present, the plurality of R907 are mutually the same or different;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different; and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different.
In the organic EL device according to the present exemplary embodiment, the group represented by the formula (11) is preferably a group represented by a formula (111) below.
In the formula (111): X1 is CR123R124, an oxygen atom, a sulfur atom, or NR125;
L111 and L112 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
ma is 0, 1, 2, 3, or 4;
mb is 0, 1, 2, 3, or 4;
ma+mb is 0, 1, 2, 3, or 4;
Ar101 represents the same as Ar101 in the formula (11);
R121, R122, R123, R124, and R125 are each dependently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
mc is 3;
three R121 are mutually the same or different;
and is 3; and
three R122 are mutually the same or different.
Among positions *1 to *8 of carbon atoms in the cyclic structure represented by a formula (111a) below in the group represented by the formula (111), L111 is bonded to one of positions *1 to *4, R121 is bonded to three positions of the rest of *1 to *4, L112 is bonded to one of positions *5 to *8, and R122 is bonded to three positions of the rest of *5 to *8.
For instance, in the group represented by the formula (111), when L111 and L112 are bonded to *2 and *7 positions, respectively, of the carbon atom of the cyclic structure represented by the formula (111a), the group represented by the formula (111) is represented by a formula (111b) below.
In the formula (111b): X1, L111, L112, ma, mb, Ar101, R121, R122, R123, R124, and R125 each independently represent the same as X1, L111, L112, ma, mb, Ar101, R121, R122, R123, R124, and R125 in the formula (111);
a plurality of R121 are mutually the same or different; and
a plurality of R122 are mutually the same or different.
In the organic EL device according to the present exemplary embodiment, the group represented by the formula (111) is preferably a group represented by the formula (111b).
In the organic EL device according to the present exemplary embodiment, it is preferable that: ma is 0, 1, or 2; and mb is 0, 1, or 2.
In the organic EL device according to the present exemplary embodiment, it is preferable that: ma is 0 or 1; and mb is 0 or 1.
In the organic EL device according to the present exemplary embodiment, Ar101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is preferable that: Ar101 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
In the organic EL device according to the present exemplary embodiment, it is also preferable that: Ar101 is a group represented by a formula (12), a formula (13), or a formula (14) below.
In the formulae (12), (13), and (14):
R111 to R120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R124, a group represented by —COOR125, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
* in the formula (12), the formula (13) and the formula (14) represents a bonding position to L101 in the formula (11), or a bonding position to L112 in the formula (111) or the formula (111b).
The first compound of the organic EL device according to the present exemplary embodiment is preferably represented by a formula (101) below.
In the formula (101): R101 to R120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
one of R101 to R110 represents a bonding position to L101, and one of R111 to R120 represents a bonding position to L101;
L101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
mx is 0, 1, 2, 3, 4, or 5; and
when two or more L101 are present, the two or more L101 are mutually the same or different.
In the first compound represented by the formula (101), it is preferable that:
R101 to R110, and R111 to R120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
one of R101 to R110 represents a bonding position to L101, and one of R111 to R120 represents a bonding position to L101;
L101 is a single bond, a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 24 ring atoms;
mx is 1, 2, 3, 4, or 5; and
when two or more L101 are present, the two or more L101 are mutually the same or different.
In the first compound represented by the formula (101), it is also preferable that:
R101 to R110, and R111 to R120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
one of R101 to R110 represents a bonding position to L101, and one of R111 to R120 represents a bonding position to L101;
L101 is a divalent group derived by removing one hydrogen atom from an aryl ring of a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group or a substituted or unsubstituted 2-naphthyl group;
mx is 1, 2, or 3; and
when two or more L101 are present, the two or more L101 are mutually the same or different.
In the organic EL device according to the present exemplary embodiment, it is preferable that the first compound is represented by a formula (1010), a formula (1011), a formula (1012), a formula (1013), a formula (1014), or a formula (1015) below.
In the formulae (1010) to (1015):
R101 to R120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
mx is 0, 1, 2, 3, 4, or 5; and
when two or more L101 are present, the two or more L101 are mutually the same or different.
The compound represented by the formula (1010) corresponds to a compound, in which R103 represents a bonding position to L101 and R120 represents a bonding position to L101.
The compound represented by the formula (1011) corresponds to a compound, in which R103 represents a bonding position to L101 and R111 represents a bonding position to L101.
The compound represented by the formula (1012) corresponds to a compound, in which R103 represents a bonding position to L101 and R118 represents a bonding position to L101.
The compound represented by the formula (1013) corresponds to a compound, in which R102 represents a bonding position to L101 and R111 represents a bonding position to L101.
The compound represented by the formula (1014) corresponds to a compound, in which R102 represents a bonding position to L101 and R118 represents a bonding position to L101.
The compound represented by the formula (1015) corresponds to a compound, in which R105 represents a bonding position to L101 and R111 represents a bonding position to L101.
The first compound of the organic EL device according to the present exemplary embodiment is preferably represented by the formula (1010).
In the organic EL device according to the present exemplary embodiment, R101 to R110 not being the bonding position to L101 are each preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the organic EL device according to the present exemplary embodiment, R101 to R110 not being the bonding position to L101 are each preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, R101 to R110 not being the bonding position to L101 are each preferably a hydrogen atom.
In the organic EL device according to the present exemplary embodiment, R111 to R120 not being the bonding position to L101 are each preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the organic EL device according to the present exemplary embodiment, R111 to R120 not being the bonding position to L101 are each preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, R111 to R120 not being the bonding position to L101 are each preferably a hydrogen atom.
In the organic EL device according to the present exemplary embodiment, it is preferable that: L101 is a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that L101 is a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that L101 is a single bond, or a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that L101 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that L101 is a single bond, a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that L101 is a single bond, or a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that L101 is a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms.
In the formulae (1010) to (1015), it is also preferable that L101 is a divalent group derived by removing one hydrogen atom from an aryl ring of a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group or a substituted or unsubstituted 2-naphthyl group, and mx is 1, 2, or 3.
L101 is also preferably a substituted or unsubstituted arylene group selected from the group consisting of groups represented by formulae (TEMP-42) to (TEMP-52), and (TEMP-63) to (TEMP-68) below.
In the formulae (TEMP-42) to (TEMP-52), and (TEMP-63) to (TEMP-68), Q1 to Q10 are each independently a hydrogen atom, or a substituent, Q1 to Q10 as the substituent are each independently an unsubstituted phenyl group, an unsubstituted 1-naphthyl group or an unsubstituted 2-naphthyl group, and * represents a bonding position.
L101 is also preferably a divalent group represented by a formula (112) below.
In the formula (112): L101 is a divalent group derived by removing one hydrogen atom from an aryl ring of a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group or a substituted or unsubstituted 2-naphthyl group;
L102 is an unsubstituted phenyl group, an unsubstituted 1-naphthyl group, or an unsubstituted 2-naphthyl group;
mx is 1, 2, or 3;
my is 0, 1, or 2;
mx+my is 1, 2, or 3;
when two or more L101 are present, the two or more L101 are mutually the same or different;
when two or more L102 are present, the two or more L102 are mutually the same or different; and
* in the formula (112) represents a bonding position.
The group represented by -(L101)mx- is preferably a group represented by any one of formulae (113) to (122) below.
* in the formulae (113) to (122) each represent a bonding position.
In the organic EL device according to the present exemplary embodiment, mx is also preferably 1, 2, or 3.
In the organic EL device according to the present exemplary embodiment, mx is also preferably 1 or 2.
In the organic EL device according to the present exemplary embodiment, it is also preferable that mx is 1, 2, or 3; and
L101 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that mx is 1 or 2; and
L101 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.
In the organic EL device according to the present exemplary embodiment, it is also preferable that mx is 1 or 2; and
L101 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is preferable that: the first compound is represented by a formula (102) below.
In the formula (102): R101 to R120 each independently represent the same as R101 to R120 of the formula (101);
one of R101 to R110 represents a bonding position to L111, and one of R111 to R120 represents a bonding position to L112;
X1 is CR123R124, an oxygen atom, a sulfur atom, or NR125;
L111 and L112 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
ma is 0, 1, 2, 3, or 4;
mb is 0, 1, 2, 3, or 4;
ma+mb is 0, 1, 2, 3, or 4;
R121, R122, R123, R124, and R125 are each dependently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
mc is 3;
three R121 are mutually the same or different;
and is 3; and
three R122 are mutually the same or different.
In the compound represented by the formula (102), it is preferable that: ma is 0, 1, or 2; and mb is 0, 1, or 2.
In the compound represented by the formula (102), it is preferable that: ma is 0 or 1; and mb is 0 or 1.
In the compound represented by the formula (102), it is preferable that L111 and L112 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 24 ring atoms.
In the compound represented by the formula (102), it is preferable that:
ma is 1, 2, or 3;
mb is 1, 2, or 3; and
ma+mb is 2, 3, or 4.
In the compound represented by the formula (102), it is preferable that:
ma is 1 or 2; and
mb is 1 or 2.
In the compound represented by the formula (102), it is preferable that:
ma is 1; and
mb is 1.
In the organic EL device according to the present exemplary embodiment, R101 to R110 not being the bonding position to L111 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the organic EL device according to the present exemplary embodiment, R101 to R110 not being the bonding position to L111 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, R101 to R110 not being the bonding position to L111 are each preferably a hydrogen atom.
In the organic EL device according to the present exemplary embodiment, R111 to R120 not being the bonding position to L112 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the organic EL device according to the present exemplary embodiment, R111 to R120 not being the bonding position to L112 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, R111 to R120 not being the bonding position to L112 are each preferably a hydrogen atom.
In the organic EL device according to the present exemplary embodiment, it is preferable that: two or more of R101 to R110 are groups represented by the formula (11).
In the organic EL device according to the present exemplary embodiment, it is preferable that: two or more of R101 to R110 are groups represented by the formula (11), and Ar101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is preferable that: Ar101 is not a substituted or unsubstituted pyrenyl group;
L101 is not a substituted or unsubstituted pyrenylene group; and
the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms for R101 to R110 not being the group represented by the formula (11) is not a substituted or unsubstituted pyrenyl group.
In the organic EL device according to the present exemplary embodiment, it is preferable that: R101 to R110 that are not the group represented by the formula (11) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the organic EL device according to the present exemplary embodiment, it is preferable that: R101 to R110 that are not the group represented by the formula (11) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, R101 to R110 not being the group represented by the formula (11) are each preferably a hydrogen atom.
In the first compound and the second compound, the groups specified to be “substituted or unsubstituted” are each preferably an “unsubstituted” group.
In the organic EL device according to the present exemplary embodiment, for instance, two of R101 to R110 in the first compound represented by the formula (1) are groups represented by the formula (11).
In the organic EL device according to the present exemplary embodiment, for instance, three of R101 to R110 in the first compound represented by the formula (1) are groups represented by the formula (11).
In the organic EL device according to the present exemplary embodiment, for instance, four of R101 to R110 in the first compound represented by the formula (1) are groups represented by the formula (11).
In the organic EL device according to the present exemplary embodiment, for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11) and mx is 1 or more.
In the organic EL device according to the present exemplary embodiment, it is preferable that: for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11), mx is 0, and Ar101 is a substituted or unsubstituted aryl group.
In the organic EL device according to the present exemplary embodiment, for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11), mx is 0, and Ar101 is a substituted or unsubstituted heterocyclic group including a nitrogen atom.
In the organic EL device according to the present exemplary embodiment, for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11), mx is 0, and Ar101 is a substituted or unsubstituted heterocyclic group including a sulfur atom.
In the organic EL device according to the present exemplary embodiment, for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11), mx is 0, and Ar101 is a substituted or unsubstituted furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, or diazanaphthobenzofuranyl group.
In the organic EL device according to the present exemplary embodiment, for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11), mx is 0, and Ar101 is a group selected from the group consisting of unsubstituted furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
In the organic EL device according to the present exemplary embodiment, for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11), mx is 0, and Ar101 is a substituted or unsubstituted dibenzofuranyl group.
In the organic EL device according to the present exemplary embodiment, for instance, one of R101 to R110 in the first compound represented by the formula (1) is a group represented by the formula (11), mx is 0, and Ar101 is an unsubstituted dibenzofuranyl group.
In the organic EL device according to the present exemplary embodiment, for instance, mx in the first compound represented by the formula (101) is 2 or more.
In the organic EL device according to the present exemplary embodiment, for instance, mx in the first compound represented by the formula (101) is 1 or more, and L101 is an arylene group having 6 to 24 ring carbon atoms or a divalent heterocyclic group having 5 to 24 ring atoms.
In the organic EL device according to the present exemplary embodiment, for instance, mx in the first compound represented by the formula (101) is 1 or more, and L101 is an arylene group having 6 to 18 ring carbon atoms or a divalent heterocyclic group having 5 to 18 ring atoms.
Method of Manufacturing First Compound
The first compound can be manufactured by a known method. The first compound can also be manufactured based on a known method through a known alternative reaction using a known material(s) tailored for the target compound.
Specific examples of the first compound is exemplified by compounds below. It should however be noted that the invention is not limited by the specific examples of the first compound.
The first compound is also preferably one of compounds represented by formulae (PY-1) to (PY-12) below.
Second Compound
The second compound of the organic EL device according to the present exemplary embodiment is represented by a formula (2) below.
In the formula (2): R201 to R208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L201 and L202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and
Ar201 and Ar202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the second compound according to the present exemplary embodiment: R901, R902, R903, R904, R905, R906, R907, R801, and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R906 are present, the plurality of R906 are mutually the same or different;
when a plurality of R907 are present, the plurality of R907 are mutually the same or different;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different; and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different.
In the organic EL device according to the present exemplary embodiment, it is preferable that: R201 to R208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, or a nitro group;
L201 and L202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and
Ar201 and Ar202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the organic EL device according to the present exemplary embodiment, it is preferable that: L201 and L202 are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; and
Ar201 and Ar202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is preferable that: Ar201 and Ar202 are each independently a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.
In the organic EL device according to the present exemplary embodiment, it is preferable that the second compound represented by the formula (2) is a compound represented by a formula (201), a formula (202), a formula (203), a formula (204), a formula (205), a formula (206), a formula (207), a formula (208), or a formula (209) below.
In the formulae (201) to (209):
L201 and Arm represent the same as L201 and Arm in the formula (2); and
R201 to R208 each independently represent the same as R201 to R208 of the formula (2).
It is also preferable that the second compound represented by the formula (2) is a compound represented by a formula (221), a formula (222), a formula (223), a formula (224), a formula (225), a formula (226), a formula (227), a formula (228), or a formula (229) below.
In the formulae (221), (222), (223), (224), (225), (226), (227), (228), and (229):
R201 and R203 to R208 each independently represent the same as R201 and R203 to R208 in the formula (2);
L201 and Ar201 each represent the same as L201 and Ar201 in the formula (2);
L203 represents the same as L201 in the formula (2);
L203 and L201 are mutually the same or different;
Ar203 represents the same as Ar201 in the formula (2); and
Ar203 and Ar201 are mutually the same or different.
It is also preferable that the second compound represented by the formula (2) is a compound represented by a formula (241), a formula (242), a formula (243), a formula (244), a formula (245), a formula (246), a formula (247), a formula (248), or a formula (249) below.
In the formulae (241), (242), (243), (244), (245), (246), (247), (248), and (249):
R201, R202, and R204 to R208 each independently represent the same as R201, R202, and R204 to R208 in the formula (2);
L203 represents the same as L201 in the formula (2);
L203 and L201 are mutually the same or different;
Ar203 represents the same as Ar201 in the formula (2); and
Ar203 and Ar201 are mutually the same or different.
In the second compound represented by the formula (2), R201 to R208 not being the group represented by the formula (21) are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a group represented by —Si(R901)(R902)(R903).
L101 is preferably a single bond, or an unsubstituted arylene group having 6 to 22 ring carbon atoms, and
Ar101 is a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.
In the organic EL device according to the present exemplary embodiment, it is preferable that: R201 to R208 in the second compound represented by the formula (2) are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a group represented by —Si(R901)(R902)(R903).
In the organic EL device according to the present exemplary embodiment, R201 to R208 in the second compound represented by the formula (2) are each preferably a hydrogen atom.
In the second compound, the groups specified to be “substituted or unsubstituted” are each preferably an “unsubstituted” group.
In the organic EL device according to the present exemplary embodiment, for instance, Ar201 in the second compound represented by the formula (2) is a substituted or unsubstituted dibenzofuranyl group.
In the organic EL device according to the present exemplary embodiment, for instance, Ar201 in the second compound represented by the formula (2) is an unsubstituted dibenzofuranyl group.
In the organic EL device according to the present exemplary embodiment, for instance, at least one hydrogen atom is included in the second compound represented by the formula (2), the hydrogen atom including at least one deuterium atom.
In the organic EL device according to the present exemplary embodiment, for instance, L201 in the second compound represented by the formula (2) is one of TEMP-63 to TEMP-68.
In the organic EL device according to the present exemplary embodiment, for instance, Ar201 in the second compound represented by the formula (2) is at least one substituted or unsubstituted group selected from the group consisting of anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluoranthenyl group, benzofluoranthenyl group, and perylenyl group.
In the organic EL device according to the present exemplary embodiment, for instance, Ar201 in the second compound represented by the formula (2) is a substituted or unsubstituted fluorenyl group.
In the organic EL device according to the present exemplary embodiment, for instance, Ar201 in the second compound represented by the formula (2) is a substituted or unsubstituted xanthenyl group.
In the organic EL device according to the present exemplary embodiment, for instance, Ar201 in the second compound represented by the formula (2) is a benzoxanthenyl group.
Method of Manufacturing Second Compound
The second compound can be manufactured by a known method. The second compound can also be manufactured based on a known method through a known alternative reaction using a known material(s) tailored for the target compound.
Specific examples of the second compound is exemplified by compounds below. It should however be noted that the invention is not limited by the specific examples of the second compound.
Examples of Combination of First Compound and Second Compound
In the organic EL device according to the present exemplary embodiment, for instance, it is also preferable that the first emitting layer contains the first compound shown in combinations below and the second emitting layer contains the second compound shown in the combinations below. It should however be noted that the invention is not limited by the specific examples of these combinations.
The first compound is BH1 and the second compound is BH2-19.
The first compound is BH1 and the second compound is BH2-7.
The first compound is BH1 and the second compound is BH2-20.
The first compound is BH1 and the second compound is BH2-31.
The first compound is BH1 and the second compound is BH2-32.
The first compound is BH1 and the second compound is BH2-33.
The first compound is BH1 and the second compound is BH2-5.
The first compound is BH1 and the second compound is BH2-8.
The first compound is BH1 and the second compound is BH2.
The first compound is BH1 and the second compound is BH2-30.
The first compound is BH1 and the second compound is BH2 and BH2-30.
The first compound is BH1 and the second compound is BH2-9.
The first compound is BH1 and the second compound is BH2-3.
The first compound is BH1 and the second compound is BH2-34.
The first compound is BH1 and the second compound is BH2-35.
The first compound is BH1 and the second compound is BH2-36.
The first compound is BH1 and the second compound is BH2-37.
The first compound is BH1-84 and the second compound is BH2-19.
The first compound is BH1-84 and the second compound is BH2-7.
The first compound is BH1-84 and the second compound is BH2-20.
The first compound is BH1-84 and the second compound is BH2-31.
The first compound is BH1-84 and the second compound is BH2-32.
The first compound is BH1-84 and the second compound is BH2-33.
The first compound is BH1-84 and the second compound is BH2-5.
The first compound is BH1-84 and the second compound is BH2-8.
The first compound is BH1-84 and the second compound is BH2.
The first compound is BH1-84 and the second compound is BH2-30.
The first compound is BH1-84 and the second compound is BH2 and BH2-30.
The first compound is BH1-84 and the second compound is BH2-9.
The first compound is BH1-84 and the second compound is BH2-3.
The first compound is BH1-84 and the second compound is BH2-34.
The first compound is BH1-84 and the second compound is BH2-35.
The first compound is BH1-84 and the second compound is BH2-36.
The first compound is BH1-84 and the second compound is BH2-37.
The first compound is BH1-85 and the second compound is BH2-19.
The first compound is BH1-85 and the second compound is BH2-7.
The first compound is BH1-85 and the second compound is BH2-20.
The first compound is BH1-85 and the second compound is BH2-31.
The first compound is BH1-85 and the second compound is BH2-32.
The first compound is BH1-85 and the second compound is BH2-33.
The first compound is BH1-85 and the second compound is BH2-5.
The first compound is BH1-85 and the second compound is BH2-8.
The first compound is BH1-85 and the second compound is BH2.
The first compound is BH1-85 and the second compound is BH2-30.
The first compound is BH1-85 and the second compound is BH2 and BH2-30.
The first compound is BH1-85 and the second compound is BH2-9.
The first compound is BH1-85 and the second compound is BH2-3.
The first compound is BH1-85 and the second compound is BH2-34.
The first compound is BH1-85 and the second compound is BH2-35.
The first compound is BH1-85 and the second compound is BH2-36.
The first compound is BH1-85 and the second compound is BH2-37.
The first compound is BH1-86 and the second compound is BH2-19.
The first compound is BH1-86 and the second compound is BH2-7.
The first compound is BH1-86 and the second compound is BH2-20.
The first compound is BH1-86 and the second compound is BH2-31.
The first compound is BH1-86 and the second compound is BH2-32.
The first compound is BH1-86 and the second compound is BH2-33.
The first compound is BH1-86 and the second compound is BH2-5.
The first compound is BH1-86 and the second compound is BH2-8.
The first compound is BH1-86 and the second compound is BH2.
The first compound is BH1-86 and the second compound is BH2-30.
The first compound is BH1-86 and the second compound is BH2 and BH2-30.
The first compound is BH1-86 and the second compound is BH2-9.
The first compound is BH1-86 and the second compound is BH2-3.
The first compound is BH1-86 and the second compound is BH2-34.
The first compound is BH1-86 and the second compound is BH2-35.
The first compound is BH1-86 and the second compound is BH2-36.
The first compound is BH1-86 and the second compound is BH2-37.
The first compound is BH1-87 and the second compound is BH2-19.
The first compound is BH1-87 and the second compound is BH2-7.
The first compound is BH1-87 and the second compound is BH2-20.
The first compound is BH1-87 and the second compound is BH2-31.
The first compound is BH1-87 and the second compound is BH2-32.
The first compound is BH1-87 and the second compound is BH2-33
The first compound is BH1-87 and the second compound is BH2-5.
The first compound is BH1-87 and the second compound is BH2-8.
The first compound is BH1-87 and the second compound is BH2.
The first compound is BH1-87 and the second compound is BH2-30.
The first compound is BH1-87 and the second compound is BH2 and BH2-30.
The first compound is BH1-87 and the second compound is BH2-9.
The first compound is BH1-87 and the second compound is BH2-3.
The first compound is BH1-87 and the second compound is BH2-34.
The first compound is BH1-87 and the second compound is BH2-35.
The first compound is BH1-87 and the second compound is BH2-36.
The first compound is BH1-87 and the second compound is BH2-37.
The first compound is BH1-88 and the second compound is BH2-19.
The first compound is BH1-88 and the second compound is BH2-7.
The first compound is BH1-88 and the second compound is BH2-20.
The first compound is BH1-88 and the second compound is BH2-31.
The first compound is BH1-88 and the second compound is BH2-32.
The first compound is BH1-88 and the second compound is BH2-33.
The first compound is BH1-88 and the second compound is BH2-5.
The first compound is BH1-88 and the second compound is BH2-8.
The first compound is BH1-88 and the second compound is BH2.
The first compound is BH1-88 and the second compound is BH2-30.
The first compound is BH1-88 and the second compound is BH2 and BH2-30.
The first compound is BH1-88 and the second compound is BH2-9.
The first compound is BH1-88 and the second compound is BH2-3.
The first compound is BH1-88 and the second compound is BH2-34.
The first compound is BH1-88 and the second compound is BH2-35.
The first compound is BH1-88 and the second compound is BH2-36.
The first compound is BH1-88 and the second compound is BH2-37.
The first compound is BH1-89 and the second compound is BH2-19.
The first compound is BH1-89 and the second compound is BH2-7.
The first compound is BH1-89 and the second compound is BH2-20.
The first compound is BH1-89 and the second compound is BH2-31.
The first compound is BH1-89 and the second compound is BH2-32.
The first compound is BH1-89 and the second compound is BH2-33.
The first compound is BH1-89 and the second compound is BH2-5.
The first compound is BH1-89 and the second compound is BH2-8.
The first compound is BH1-89 and the second compound is BH2.
The first compound is BH1-89 and the second compound is BH2-30.
The first compound is BH1-89 and the second compound is BH2 and BH2-30.
The first compound is BH1-89 and the second compound is BH2-9.
The first compound is BH1-89 and the second compound is BH2-3.
The first compound is BH1-89 and the second compound is BH2-34.
The first compound is BH1-89 and the second compound is BH2-35.
The first compound is BH1-89 and the second compound is BH2-36.
The first compound is BH1-89 and the second compound is BH2-37.
The first compound is BH1-90 and the second compound is BH2-19.
The first compound is BH1-90 and the second compound is BH2-7.
The first compound is BH1-90 and the second compound is BH2-20.
The first compound is BH1-90 and the second compound is BH2-31.
The first compound is BH1-90 and the second compound is BH2-32.
The first compound is BH1-90 and the second compound is BH2-33.
The first compound is BH1-90 and the second compound is BH2-5.
The first compound is BH1-90 and the second compound is BH2-8.
The first compound is BH1-90 and the second compound is BH2.
The first compound is BH1-90 and the second compound is BH2-30.
The first compound is BH1-90 and the second compound is BH2 and BH2-30.
The first compound is BH1-90 and the second compound is BH2-9.
The first compound is BH1-90 and the second compound is BH2-3.
The first compound is BH1-90 and the second compound is BH2-34.
The first compound is BH1-90 and the second compound is BH2-35.
The first compound is BH1-90 and the second compound is BH2-36.
The first compound is BH1-90 and the second compound is BH2-37.
Third Compound and Fourth Compound
The first emitting layer of the organic EL device according to the present exemplary embodiment also preferably further contains a fluorescent third compound.
The second emitting layer of the organic EL device according to the present exemplary embodiment also preferably further contains a fluorescent fourth compound.
When the first emitting layer contains the third compound and the second emitting layer contains the fourth compound, the third compound and the fourth compound are mutually the same or different.
The third compound and the fourth compound are each independently at least one compound selected from the group consisting of a compound represented by a formula (3) below, a compound represented by a formula (4) below, a compound represented by a formula (5) below, a compound represented by a formula (6) below, a compound represented by a formula (7) below, a compound represented by a formula (8) below, a compound represented by a formula (9) below, and a compound represented by a formula (10) below.
Compound Represented by Formula (3)
The compound represented by the formula (3) will be described below.
In the formula (3): at least one combination of adjacent two or more of R301 to R310 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one of R301 to R310 is each a monovalent group represented by a formula (31) below; and
R301 to R310 forming neither the monocyclic ring nor the fused ring and not being the monovalent group represented by the formula (31) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (31): Ar301 and Ar302 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L301 to L303 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
* represents a bonding position to the pyrene ring in the formula (3).
R901, R902, R903, R904, R905, R906, and R907 in the third and fourth compounds are each dependently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
when a plurality of R901 are present, the plurality of R901 are mutually the same or different;
when a plurality of R902 are present, the plurality of R902 are mutually the same or different;
when a plurality of R903 are present, the plurality of R903 are mutually the same or different;
when a plurality of R904 are present, the plurality of R904 are mutually the same or different;
when a plurality of R905 are present, the plurality of R905 are mutually the same or different;
when a plurality of R906 are present, the plurality of R906 are mutually the same or different; and
when a plurality of R907 are present, the plurality of R907 are mutually the same or different.
In the formula (3), two of R301 to R310 are preferably groups represented by the formula (31).
In some embodiments, the compound represented by the formula (3) is represented by a formula (33) below.
In the formula (33): R311 to R315 represent the same as R301 to R310 in the formula (3) that are not the monovalent group represented by the formula (31);
L311 to L316 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
Ar312, Ar313, Ar315, and Ar316 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (31), L301 is preferably a single bond, and L302 and L303 are each preferably a single bond.
In some embodiments, the compound represented by the formula (3) is represented by a formula (34) or a formula (35) below.
In the formula (34): R311 to R318 represent the same as R301 to R310 in the formula (3) that are not the monovalent group represented by the formula (31);
L312, L313, L315 and L316 each independently represent the same as L312, L313, L315 and L316 in the formula (33); and
Ar312, Ar313, Ar315 and Ar316 each independently represent the same as Ar312, Ar313, Ar315 and Ar316 in the formula (33).
In the formula (35): R311 to R318 represent the same as R301 to R310 in the formula (3) that are not the monovalent group represented by the formula (31); and
Ar312, Ar313, Ar315 and Ar316 each independently represent the same as Ar312, Ar313, Ar315 and Ar316 in the formula (33).
In the formula (31), at least one of Ar301 and Ar302 is preferably a group represented by a formula (36) below.
In the formulae (33) to (35), at least one of Ar312 and Ar313 is preferably a group represented by the formula (36) below.
In the formulae (33) to (35), at least one of Ar315 and Ar316 is preferably a group represented by the formula (36) below.
In the formula (36): X3 represents an oxygen atom or a sulfur atom;
at least one combination of adjacent two or more of R321 to R327 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R321 to R327 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
* represents a bonding position to L302, L303, L312, L313, L315, or L316.
X3 is preferably an oxygen atom.
At least one of R321 to R327 is also preferably: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (31), it is preferable that Ar301 is the group represented by the formula (36) and Ar302 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the formulae (33) to (35), it is preferable that Ar312 is the group represented by the formula (36) and Ar313 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the formulae (33) to (35), it is preferable that Ar315 is the group represented by the formula (36) and Ar316 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, the compound represented by the formula (3) is represented by a formula (37) below.
In the formula (37): R311 to R318 represent the same as R301 to R310 in the formula (3) that are not the monovalent group represented by the formula (31);
at least one combination of adjacent two or more of R321 to R327 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of R341 to R347 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R321 to R327 and R341 to R347 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
R331 to R335, and R351 to R335 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Specific examples of the compound represented by the formula (3) include compounds shown below.
Compound Represented by Formula (4)
The compound represented by the formula (4) will be described below.
In the formula (4): Z are each independently CRa or a nitrogen atom;
A1 ring and A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
when a plurality of Ra are present, at least one combination of adjacent two or more of Ra are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
n21 and n22 are each independently 0, 1, 2, 3 or 4;
when a plurality of Rb are present, at least one combination of adjacent two or more of Rb are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
when a plurality of Rc are present, at least one combination of adjacent two or more of Rc are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
Ra, Rb, and Rc not forming the monocyclic ring and not forming the fused ring are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
The “aromatic hydrocarbon ring” for the A1 ring and A2 ring has the same structure as the compound formed by introducing a hydrogen atom to the “aryl group” described above.
Ring atoms of the “aromatic hydrocarbon ring” for the A1 ring and the A2 ring include two carbon atoms on a fused bicyclic structure at the center of the formula (4).
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include a compound formed by introducing a hydrogen atom to the “aryl group” described in the specific example group G1.
The “heterocycle” for the A1 ring and A2 ring has the same structure as the compound formed by introducing a hydrogen atom to the “heterocyclic group” described above.
Ring atoms of the “heterocycle” for the A1 ring and the A2 ring include two carbon atoms on a fused bicyclic structure at the center of the formula (4).
Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include a compound formed by introducing a hydrogen atom to the “heterocyclic group” described in the specific example group G2.
Rb is bonded to any one of carbon atoms forming the aromatic hydrocarbon ring for the A1 ring or any one of the atoms forming the heterocycle for the A1 ring.
Rc is bonded to any one of carbon atoms forming the aromatic hydrocarbon ring for the A2 ring or any one of the atoms forming the heterocycle for the A2 ring.
At least one of Ra, Rb, and Rc is preferably a group represented by the formula (4a) below. More preferably, at least two of Ra, Rb, and Rc are groups represented by the formula (4a).
In the formula (4a): L401 is preferably a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
Ar401 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by a formula (4b) below.
In the formula (4b): L402 and L403 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
a combination of Ar402 and Ar403 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
Ar402 and Ar403 not forming the monocyclic ring and not forming the fused ring are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, the compound represented by the formula (4) is represented by a formula (42) below.
In the formula (42): at least one combination of adjacent two or more of R401 to R411 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
one or more of R401 to R411 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
At least one of R401 to R411 is preferably a group represented by the formula (4a). More preferably, at least two of R401 to R411 are groups represented by the formula (21a).
R404 and R411 are preferably groups represented by the formula (4a).
In some embodiments, the compound represented by the formula (4) is a compound formed by bonding a moiety represented by a formula (4-1) or a formula (4-2) below to the A1 ring.
Further, in some embodiments, the compound represented by the formula (42) is a compound formed by bonding the moiety represented by the formula (4-1) or the formula (4-2) to the ring bonded with R404 to R407.
In the formula (4-1), two bonds * are each independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocycle for the A1 ring in the formula (4) or bonded to one of R404 to R407 in the formula (42);
in the formula (4-2), three bonds * are each independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocycle for the A1 ring in the formula (4) or bonded to one of R404 to R407 in the formula (42);
at least one combination of adjacent two or more of R421 to R427 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
at least one combination of adjacent two or more of R431 to R438 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
R421 to R427 and R431 to R438 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, the compound represented by the formula (4) is a compound represented by a formula (41-3), a formula (41-4) or a formula (41-5) below.
In the formulae (41-3), (41-4), and (41-5):
A1 ring is as defined for the formula (4);
R421 to R427 each independently represent the same as R421 to R427 in the formula (4-1); and
R440 to R448 each independently represent the same as R401 to R411 in the formula (42).
In some embodiments, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms for the A1 ring in the formula (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring.
In some embodiments, a substituted or unsubstituted heterocycle having 5 to 50 ring atoms for the A1 ring in the formula (41-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
In some embodiments, the compound represented by the formula (4) or the formula (42) is a compound selected from the group consisting of compounds represented by formulae (461) to (467) below.
In the formulae (461), (462), (463), (464), (465), (466), and (467):
R421 to R427 each independently represent the same as R421 to R427 in the formula (4-1); and
R431 to R438 each independently represent the same as R431 to R438 in the formula (4-2);
R440 to R448 and R451 to R454 each independently represent the same as R401 to R411 in the formula (42);
X4 is an oxygen atom, NR801, or C(R802)(R803);
R801, R802, and R803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different;
when a plurality of R802 are present, the plurality of R802 are mutually the same or different; and
when a plurality of R803 are present, the plurality of R803 are mutually the same or different.
In some embodiment, at least one combination of adjacent two or more of R401 to R411 in the compound represented by the formula (42) are mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring. This embodiment will be described in detail below as a compound represented by a formula (45).
Compound Represented by Formula (45)
The compound represented by the formula (45) will be described below.
In the formula (45): two ore more of combinations selected from the group consisting of a combination of R461 and R462, a combination of R462 and R463, a combination of R464 and R465, a combination of R465 and R466, a combination of R466 and R467, a combination of R468 and R469, a combination of R469 and R470, and a combination of R470 and R471 are mutually bonded to form a substituted or unsubstituted monocyclic ring or mutually bonded to form a substituted or unsubstituted fused ring.
However: the combination of R461 and R462 and the combination of R462 and R463; the combination of R464 and R465 and the combination of R465 and R466; the combination of R465 and R466 and the combination of R466 and R467; the combination of R468 and R469 and the combination of R469 and R470; and the combination of R469 and R470 and the combination of R470 and R471 do not simultaneously form a ring;
the two or more rings formed by R461 to R471 are mutually the same or different; and
R461 to R471 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), or —N(R906)(R907); a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (45), Rn and Rn+1 (n being an integer selected from 461, 462, 464 to 466, and 468 to 470) are mutually bonded to form a substituted or unsubstituted monocyclic ring or fused ring together with two ring-forming carbon atoms bonded with Rn and Rn+1. The ring is preferably formed of atoms selected from the group consisting of a carbon atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and is made of 3 to 7, more preferably 5 or 6 atoms.
The number of the above cyclic structures in the compound represented by the formula (45) is, for instance, 2, 3, or 4. The two or more of the cyclic structures may be present on the same benzene ring on the basic skeleton represented by the formula (45) or may be present on different benzene rings. For instance, when three cyclic structures are present, each of the cyclic structures may be present on corresponding one of the three benzene rings of the formula (45).
Examples of the above cyclic structures in the compound represented by the formula (45) include structures represented by formulae (451) to (460) below.
In the formulae (451) to (457):
each combination of *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent the two ring-forming carbon atoms respectively bonded with Rn and Rn+1;
the ring-forming carbon atom bonded with Rn may be any one of the two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14;
X45 is C(R4512)(R4513), NR4514, an oxygen atom, or a sulfur atom;
at least one combination of adjacent two or more of R4501 to R4506 and R4512 to R4513 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
one or more of R4501 to R4514 not forming the monocyclic ring and not forming the fused ring each independently represent the same as R461 to R471 in the formula (45).
In the formulae (458) to (460):
each combination of *1 and *2, and *3 and *4 represent the two ring-forming carbon atoms each bonded with Rn and Rn+1, the ring-forming carbon atom bonded with Rn may be any one of the two ring-forming carbon atoms represented by *1 and *2, or *3 and *4;
X45 is C(R4512)(R4513), NR4514, an oxygen atom, or a sulfur atom;
at least one combination of adjacent two or more of R4512 to R4513 and R4515 to R4525 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
one or more of R4512 to R4513, R4515 to R4514, R4522 to R4525, and R4514 not forming the monocyclic ring and not forming the fused ring each independently represent the same as R461 to R471 in the formula (45).
In the formula (45), it is preferable that at least one of R462, R464, R465, R470 or R471 (preferably, at least one of R462, R465 and R470, more preferably R462) is a group not forming the cyclic structure.
(i) A substituent, if present, of the cyclic structure formed by Rn and Rn+1 of the formula (45),
(ii) R461 to R471 not forming the cyclic structure in the formula (45), and
(iii) R4501 to R4514, R4515 to R4525 in the formulae (451) to (460) are preferably each independently any one of group selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R906)(R907), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by formulae (461) to (464) below.
In the formulae (461) to (464):
Rd is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
X46 is C(R801)(R802), NR803, an oxygen atom or a sulfur atom;
R801, R802, and R803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different;
when a plurality of R802 are present, the plurality of R802 are mutually the same or different;
when a plurality of R803 are present, the plurality of R803 are mutually the same or different;
p1 is 5;
p2 is 4;
p3 is 3;
p4 is 7; and
* in the formulae (461) to (464) each independently represent a bonding position to a cyclic structure.
R901 to R907 in the third compound and the fourth compound are as defined above.
In some embodiments, the compound represented by the formula (45) is represented by one of formulae (45-1) to (45-6) below.
In the formulae (45-1) to (45-6):
rings d to i are each dependently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; and
R461 to R471 each independently represent the same as R461 to R471 in the formula (45).
In some embodiments, the compound represented by the formula (45) is represented by one of formulae (45-7) to (45-12) below.
In the formulae (45-7) to (45-12):
rings d to f, k and j are each dependently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; and
R461 to R471 each independently represent the same as R461 to R471 in the formula (45).
In some embodiments, the compound represented by the formula (45) is represented by one of formulae (45-13) to (45-21) below.
In the formulae (45-13) to (45-21):
rings d to k are each dependently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; and
R461 to R471 each independently represent the same as R461 to R471 in the formula (45).
When the ring g or the ring h further has a substituent, examples of the substituent include a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a group represented by the formula (461), a group represented by the formula (463), and a group represented by the formula (464).
In some embodiments, the compound represented by the formula (45) is represented by one of formulae (45-22) to (45-25) below.
in the formulae (45-22) to (45-25):
X46 and X47 are each independently C(R801)(R802), NR803, an oxygen atom or a sulfur atom; and
R461 to R471 and R481 to R488 respectively represent the same as R461 to R471 of the formula (45).
R801, R802, and R803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different; and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different; and
when a plurality of R803 are present, the plurality of R803 are mutually the same or different.)
In some embodiments, the compound represented by the formula (45) is represented by a formula (45-26) below.
In the formula (45-26): X46 is C(R801)(R802), NR803, an oxygen atom or a sulfur atom;
R463, R464, R467, R468, R471, and R481 to R492 each independently represent the same as R461 to R471 in the formula (45);
R801, R802, and R803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different; and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different; and
when a plurality of R803 are present, the plurality of R803 are mutually the same or different.)
Specific examples of the compound represented by the formula (4) include compounds shown below. In the specific examples below, Ph represents a phenyl group, and D represents a deuterium atom.
Compound Represented by Formula (5)
The compound represented by the formula (5) will be described below. The compound represented by the formula (5) corresponds to the compound represented by the above-described formula (41-3).
In the formula (5): at least one combination of adjacent two or more of R501 to R507 and R511 to R517 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
one or more of R501 to R507 and R511 to R517 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
R521 and R522 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
“A combination of adjacent two or more of R501 to R507 and R511 to R517” refers to, for instance, a pair of R501 and R502, a pair of R502 and R503, a pair of R503 and R504, a pair of R505 and R506, a pair of R506 and R507, and a combination of R501, R502, and R503.
In some embodiments, at least one, preferably two of R501 to R507 and R511 to R517 are groups represented by —N(R906)(R907).
In some embodiments, R501 to R507 and R511 to R517 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, the compound represented by the formula (5) is represented by a formula (52) below.
In the formula (52): at least one combination of adjacent two or more of R531 to R534 and R541 to R544 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
one or more of R531 to R534, R541 to R544, and R551 to R552 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
R561 to R564 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, the compound represented by the formula (5) is represented by a formula (53) below.
In the formula (53), R551, R552, and R561 to R564 each independently represent the same as R551, R552, and R561 to R564 in the formula (52).
In some embodiments, R561 to R564 in the formulae (52) and (53) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).
In some embodiments, R521 and R522 in the formula (5), and R551 and R552 in the formulae (52) and (53) are each a hydrogen atom.
In some embodiments, the substituent meant by “substituted or unsubstituted” in the formulae (5), (52) and (53) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Specific examples of the compound represented by the formula (5) include compounds shown below.
The compound represented by the formula (6) will be described below.
In the formula (6): a ring, b ring and c ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
R601 and R602 are optionally each independently bonded with the a ring, b ring, or a c ring to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle; and
R601 and R602 not forming the substituted or unsubstituted heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
The a ring, b ring and c ring are each a ring (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms) fused with the fused bicyclic moiety formed of a boron atom and two nitrogen atoms at the center of the formula (6).
The “aromatic hydrocarbon ring” for the a, b, and c rings has the same structure as the compound formed by introducing a hydrogen atom to the “aryl group” described above.
Ring atoms of the “aromatic hydrocarbon ring” for the a ring include three carbon atoms on the fused bicyclic structure at the center of the formula (6).
Ring atoms of the “aromatic hydrocarbon ring” for the b ring and the c ring include two carbon atoms on a fused bicyclic structure at the center of the formula (6).
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include a compound formed by introducing a hydrogen atom to the “aryl group” described in the specific example group G1.
The “heterocycle” for the a, b, and c rings has the same structure as the compound formed by introducing a hydrogen atom to the “heterocyclic group” described above.
Ring atoms of the “heterocycle” for the a ring include three carbon atoms on the fused bicyclic structure at the center of the formula (6). Ring atoms of the “heterocycle” for the b ring and the c ring include two carbon atoms on a fused bicyclic structure at the center of the formula (6). Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include a compound formed by introducing a hydrogen atom to the “heterocyclic group” described in the specific example group G2.
R601 and R602 are optionally each independently bonded with the a ring, b ring, or c ring to form a substituted or unsubstituted heterocycle. The “heterocycle” in this arrangement includes the nitrogen atom on the fused bicyclic structure at the center of the formula (6). The heterocycle in the above arrangement optionally include a hetero atom other than the nitrogen atom. R601 and R602 bonded with the a ring, b ring, or c ring specifically means that atoms forming R601 and R602 are bonded with atoms forming the a ring, b ring, or c ring. For instance, R601 may be bonded to the a ring to form a bicyclic (or tri-or-more cyclic) fused nitrogen-containing heterocycle, in which the ring including R601 and the a ring are fused. Specific examples of the nitrogen-containing heterocycle include a compound corresponding to the nitrogen-containing bi(or-more)cyclic heterocyclic group in the specific example group G2.
The same applies to R601 bonded with the b ring, R602 bonded with the a ring, and R602 bonded with the c ring.
In some embodiments, the a ring, b ring and c ring in the formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
In some embodiments, the a ring, b ring and c ring in the formula (6) are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.
In some embodiments, R601 and R602 in the formula (6) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, the compound represented by the formula (6) is represented by a formula (62) below.
In the formula (62): R601A is optionally bonded with at least one of R611 or R621 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R602A is optionally bonded with at least one of R613 or R614A to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R601A and R602A not forming the substituted or unsubstituted heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
at least one combination of adjacent two or more of R611 to R621 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
R611 to R621 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
R601A and R602A in the formula (62) are groups corresponding to R601 and R602 in the formula (6), respectively.
For instance, R601A and R611 are optionally bonded with each other to form a bicyclic (or tri-or-more cyclic) nitrogen-containing heterocycle, in which the ring including R601A and R611 and a benzene ring corresponding to the a ring are fused. Specific examples of the nitrogen-containing heterocycle include a compound corresponding to the nitrogen-containing bi(or-more)cyclic heterocyclic group in the specific example group G2. The same applies to R601A bonded with R621, R602A bonded with R613, and R602A bonded with R614.
at least one combination of adjacent two or more of R611 to R621 are mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring.
For instance, R611 and R612 are optionally mutually bonded to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring, benzothiophene ring or the like is bonded to the six-membered ring bonded with R611 and R612, the resultant fused ring forming a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring, respectively.
In some embodiments, R611 to R621, which do not contribute to ring formation, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, R611 to R621, which do not contribute to ring formation, are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, R611 to R621, which do not contribute to ring formation, are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In some embodiments, R611 to R621, which do not contribute to ring formation, are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and
at least one of R611 to R621 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In some embodiments, the compound represented by the formula (62) is represented by a formula (63) below.
In the formula (63): R631 is optionally bonded with R646 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R633 is optionally bonded with R647 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R634 is optionally bonded with R651 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R641 is optionally bonded with R642 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
at least one combination of adjacent two or more of R631 to R651 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
R631 to R651 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
R631 are optionally mutually bonded with R646 to form a substituted or unsubstituted heterocycle. For instance, R631 and R646 are optionally bonded with each other to form a tri-or-more cyclic nitrogen-containing heterocycle, in which a benzene ring bonded with R646, a ring including a nitrogen atom, and a benzene ring corresponding to the a ring are fused. Specific examples of the nitrogen-containing heterocycle include a compound corresponding to the nitrogen-containing tri(-or-more)cyclic heterocyclic group in the specific example group G2. The same applies to R633 bonded with R647, R634 bonded with R651, and R641 bonded with R642.
In some embodiments, R631 to R651, which do not contribute to ring formation, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, R631 to R651, which do not contribute to ring formation, are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, R631 to R651, which do not contribute to ring formation, are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In some embodiments, R631 to R651, which do not contribute to ring formation, are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and
at least one of R631 to R651 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In some embodiments, the compound represented by the formula (63) is represented by a formula (63A) below.
In the formula (63A): R661 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and
R662 to R665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, R661 to R665, which do not contribute to ring formation, are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, R661 to R665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In some embodiments, the compound represented by the formula (63) is represented by a formula (63B) below.
In the formula (63B): R671 and R672 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R906)(R907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and
R673 to R675 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R906)(R907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, the compound represented by the formula (63) is represented by a formula (63B′) below.
R672 to R675 of the formula (63B′) respectively represent the same as R672 to R675 of the formula (63B).
In some embodiments, at least one of R671 to R675 is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R906)(R907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments: R672 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a group represented by —N(R906)(R907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and
R671, and R673 to R675 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a group represented by —N(R906)(R907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, the compound represented by the formula (63) is represented by a formula (63C) below.
In the formula (63C): R681 and R682 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R683 to R686 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, the compound represented by the formula (63) is represented by a formula (63C′) below.
In the formula (63C′), R683 to R686 each independently represent the same as R683 to R686 of the formula (63C).
In some embodiments, R681 to R686, which do not contribute to ring formation, are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, R681 to R686 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
The compound represented by the formula (6) is producible by initially bonding the a ring, b ring and c ring with linking groups (a group including N—R601 and a group including N—R602) to form an intermediate (first reaction), and bonding the a ring, b ring and c ring with a linking group (a group including a boron atom) to form a final product (second reaction). In the first reaction, an amination reaction (e.g. Buchwald-Hartwig reaction) is applicable. In the second reaction, Tandem Hetero-Friedel-Crafts Reactions or the like is applicable.
Specific examples of the compound represented by the formula (6) are shown below. It should however be noted that these specific examples are merely exemplary and do not limit the compound represented by the formula (6).
The compound represented by the formula (7) will be described below.
In the formula (7): r ring is a ring represented by the formula (72) or the formula (73), the r ring being fused with at any position(s) of respective adjacent rings;
q ring and s ring are each independently a ring represented by the formula (74) and fused with any position(s) of respective adjacent rings;
p ring and t ring are each independently a moiety represented by the formula (75) or the formula (76) and fused with any position(s) of respective adjacent rings;
X7 is an oxygen atom, a sulfur atom, or NR702;
when a plurality of R701 are present, adjacent ones of the plurality of R701 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R701 and R702 not forming the monocyclic ring and not forming the fused ring are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
Ar701 and Ar702 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L701 is a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
m1 is 0, 1, or 2;
m2 is 0, 1, 2, 3, or 4;
m3 is each independently 0, 1, 2, 3 or 3;
m4 is each independently 0, 1, 2, 3, 4, or 5;
when a plurality of R701 are present, the plurality of R701 are mutually the same or different;
when a plurality of X7 are present, the plurality of X7 are mutually the same or different;
when a plurality of R702 are present, the plurality of R702 are mutually the same or different;
when a plurality of Ar701 are present, the plurality of Ar701 are mutually the same or different;
when a plurality of Ar702 are present, the plurality of Ar702 are mutually the same or different; and
when a plurality of L701 are present, the plurality of L701 are mutually the same or different.
In the formula (7), each of the p ring, q ring, r ring, s ring, and t ring is fused with an adjacent ring(s) sharing two carbon atoms. The fused position and orientation are not limited but may be defined as required.
In some embodiments, in the formula (72) or the formula (73) representing the r ring, m1=0 or m2=0.
In some embodiments, the compound represented by the formula (7) is represented by any one of formulae (71-1) to (71-6) below.
In the formulae (71-1) to (71-6), R701, X7, Ar701, Ar702, L701, m1 and m3 respectively represent the same as R701, X7, Ar701, Ar702, L701, m1 and m3 in the formula (7).
In some embodiments, the compound represented by the formula (7) is represented by any one of formulae (71-11) to (71-13) below.
In the formulae (71-11) to (71-13), R701, X7, Ar701, Ar702, L701, m1, m3 and m4 respectively represent the same as R701, X7, Ar701, Ar702, L701, m1, m3 and m4 in the formula (7).
In some embodiments, the compound represented by the formula (7) is represented by any one of formulae (71-21) to (71-25) below.
In the formulae (71-21) to (71-25), R701, X7, Ar701, Ar702, L701, m1 and m4 respectively represent the same as R701, X7, Ar701, Ar702, L701, m1 and m4 in the formula (7).
In some embodiments, the compound represented by the formula (7) is represented by any one of formulae (71-31) to (71-33) below.
In the formulae (71-31) to (71-33), R701, X7, Ar701, Ar702, L701, and m2 to m4 respectively represent the same as R701, X7, Ar701, Ar702, L701, and m2 to m4 in the formula (7).
In some embodiments, Ar701 and Ar702 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, one of Ar701 and Ar702 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other of Ar701 and Ar702 is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Specific examples of the compound represented by the formula (7) include compounds shown below.
Compound Represented by Formula (8)
The con-mound represented by the formula (8) will be described below.
In the formula (8): at least one combination of R801 and R802, R802 and R803, and R803 and R804 are mutually bonded to form a divalent group represented by a formula (82) below, and
at least one combination of R805 and R806, R806 and R807, and R807 and R808 are mutually bonded to form a divalent group represented by a formula (83) below.
At least one of R801 to R804 and R811 to R814 not forming the divalent group represented by the formula (82) is a monovalent group represented by a formula (84) below;
At least one of R805 to R808 and R821 to R824 not forming the divalent group represented by the formula (83) is a monovalent group represented by a formula (84) below;
X8 is an oxygen atom, a sulfur atom, or NR809; and
R801 to R808 not forming the divalent group represented by the formula (82) or (83) and not being the monovalent group represented by the formula (84), and R811 to R814, R821 to R824 and R809 not being the monovalent group represented by the formula (84) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (84): Ar801 and Ar802 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L801 to L803 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding two, three or four groups selected from the group consisting of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
* in the formula (84) represents a bonding position to the cyclic structure represented by the formula (8) or the group represented by the formula (82) or the formula (83).
In the formula (8), the positions for the divalent group represented by the formula (82) and the divalent group represented by the formula (83) to be formed are not specifically limited but the divalent groups may be formed at any possible positions on R801 to R808.
In some embodiments, the compound represented by the formula (8) is represented by any one of formulae (81-1) to (81-6) below.
In the formulae (81-1) to (81-6):
X8 represents the same as X8 in the formula (8);
at least two of R801 to R824 are each a monovalent group represented by the formula (84); and
R801 to R824 that are not the monovalent group represented by the formula (84) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, the compound represented by the formula (8) is represented by any one of formulae (81-7) to (81-18) below.
In the formulae (81-7) to (81-18):
X8 represents the same as X8 in the formula (8);
* is a single bond to be bonded with the monovalent group represented by the formula (84); and
R801 to R824 represent the same as R801 to R824 in the formulae (81-1) to (81-6) that are not the monovalent group represented by the formula (84); and
R801 to R808 not forming the divalent group represented by the formula (82) or (83) and not being the monovalent group represented by the formula (84), and R811 to R814 and R821 to R824 not being the monovalent group represented by the formula (84) are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
The monovalent group represented by the formula (84) is preferably represented by a formula (85) or (86) below.
In the formula (85): R831 to R840 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
* in the formula (85) represents the same as * in the formula (84).
In the formula (86): Ar801, L801, and L803 represent the same as Ar801, L801, and L803 in the formula (84); and
HAr801 is a moiety represented by a formula (87) below.
In the formula (87): X81 represents an oxygen atom or a sulfur atom;
one of R841 to R848 is a single bond with L803; and
R841 to R848 not being the single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Specific examples of the compound represented by the formula (8) include compounds shown below as well as the compounds disclosed in WO 2014/104144.
Compound Represented by Formula (9)
The compound represented by the formula (9) will be described below.
In the formula (9): A91 ring and A92 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
at least one of A91 ring or A92 ring is bonded with * in a moiety represented by a formula (92) below.
In the formula (92): A93 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
X9 is NR93, C(R94)(R95), Si(R96)(R97), Ge(R98)(R99), an oxygen atom, a sulfur atom, or a selenium atom;
R91 and R92 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
R91 and R92, and R93 to R99 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
At least one ring selected from the group consisting of A91 ring and A92 ring is bonded to a bond * of the moiety represented by the formula (92). In other words, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the A91 ring in some embodiments are bonded to the bonds * in the moiety represented by the formula (92). Further, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the A92 ring in some embodiments are bonded to the bonds * in the moiety represented by the formula (92).
In some embodiments, the group represented by a formula (93) below is bonded to one or both of the A91 ring and A92 ring.
In the formula (93): Ar91 and Ar92 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L91 to L93 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent divalent heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding two, three or four groups selected from the group consisting of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
* in the formula (93) represents a bonding position to one of A91 ring and A92 ring.
In some embodiments, in addition to the A91 ring, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the A92 ring are bonded to * in the moiety represented by the formula (92). In this case, the moieties represented by the formula (92) are mutually the same or different.
In some embodiments, R91 and R92 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, R91 and R92 are mutually bonded to form a fluorene structure.
In some embodiments, the rings A91 and A92 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, example of which is a substituted or unsubstituted benzene ring.
In some embodiments, the ring A93 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, example of which is a substituted or unsubstituted benzene ring.
In some embodiments, X9 is an oxygen atom or a sulfur atom.
Specific examples of the compound represented by the formula (9) include compounds shown below.
Compound Represented by Formula (10)
The compound represented by the formula (10) will be described below.
In the formula (10): Ax1 ring is a ring represented by the formula (10a) and fused with any positions of adjacent rings;
Axe ring is a ring represented by the formula (10b) and fused with any positions of adjacent rings;
Two * in the formula (10b) are bonded to any position of Ax3 ring;
XA and XB are each independently C(R1003)(R1004), Si(R1005)(R1006), an oxygen atom or a sulfur atom;
Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
Ar1001 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
R1001 to R1006 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
mx1 is 3, mx2 is 2;
a plurality of R1001 are are mutually the same or different;
a plurality of R1002 are mutually the same or different;
ax is 0, 1, or 2;
when ax is 0 or 1, the structures enclosed by brackets indicated by “3-ax” are mutually the same or different; and
when ax is 2, the plurality of Ar1001 are mutually the same or different.
In some embodiments, Ar1001 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In some embodiments, Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, example of which is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
In some embodiments, R1003 and R1004 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In some embodiments, ax is 1.
Specific examples of the compound represented by the formula (10) include compounds shown below.
In some embodiments, the emitting layer contains, as at least one of the third compound or the fourth compound, at least one compound selected from the group consisting of the compound represented by the formula (4), the compound represented by the formula (5), the compound represented by the formula (7), the compound represented by the formula (8), the compound represented by the formula (9), and a compound represented by a formula (63a) below.
In the formula (63a): R631 is optionally bonded with R646 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R633 is optionally bonded with R647 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R634 is optionally bonded with R651 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
R641 is optionally bonded with R642 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
at least one combination of adjacent two or more of R631 to R651 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R631 to R651 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
at least one of R631 to R651 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, the compound represented by the formula (4) is the compound represented by the formula (41-3), the formula (41-4) or the formula (41-5), the A1 ring in the formula (41-5) being a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, or a substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms.
In some embodiments, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formulae (41-3), (41-4) and (41-5) is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring; and
the substituted or unsubstituted heterocycle having 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
In some embodiments, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formula (41-3), (41-4) or (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring; and
the substituted or unsubstituted heterocycle having 5 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
In some embodiments, the compound represented by the formula (4) is selected from the group consisting of a compound represented by a formula (461) below, a compound represented by a formula (462) below, a compound represented by a formula (463) below, a compound represented by a formula (464) below, a compound represented by a formula (465) below, a compound represented by a formula (466) below, and a compound represented by a formula (467) below.
In the formulae (461) to (467): at least one combination of adjacent two or more of moieties selected from R421 to R427, R431 to R436, R440 to R448, and R451 to R454 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
R437, R438, and R421 to R427, R431 to R436, R440 to R448, and R451 to R454 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
X4 is an oxygen atom, NR801, or C(R802)(R803);
R801, R802, and R803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
when a plurality of R801 are present, the plurality of R801 are mutually the same or different; and
when a plurality of R802 are present, the plurality of R802 are mutually the same or different; and
when a plurality of R803 are present, the plurality of R803 are mutually the same or different.)
In some embodiments, R421 to R427 and R440 to R448 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, R421 to R427 and R440 to R447 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
In some embodiments, the compound represented by the formula (41-3) is represented by a formula (41-3-1) below.
In the formula (41-3-1), R423, R425, R426, R442, R444, and R445 each independently represent the same as R423, R425, R426, R442, R444, and R445 in the formula (41-3).
In some embodiments, the compound represented by the formula (41-3) is represented by a formula (41-3-2) below.
In the formula (41-3-2), R421 to R427 and R440 to R448 each independently represent the same as R421 to R427 and R440 to R448 in the formula (41-3), at least one of R421 to R427 and R440 to R446 being a group represented by —N(R906)(R907).
In some embodiments, two of R421 to R427 and R440 to R446 in the formula (41-3-2) are groups represented by —N(R906)(R907).
In some embodiments, the compound represented by the formula (41-3-2) is represented by a formula (41-3-3) below.
In the formula (41-3-3), R421 to R424, R440 to R443, R447, and R448 each independently represent the same as R421 to R424, R440 to R443, R447, and R448 in the formula (41-3); and
RA, RB, RC, and RD are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
In some embodiments, the compound represented by the formula (41-3-3) is represented by a formula (41-3-4) below.
In the formula (41-3-4), R447, R448, RA, RB, RC, and RD each independently represent the same as R447, R448, RA, RB, RC, and RD in the formula (41-3-3).
In some embodiments, RA, RB, RC, and RD are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
In some embodiments, RA, RB, RC, and RD are each independently a substituted or unsubstituted phenyl group.
In some embodiments, R447 and R448 are each a hydrogen atom.
In some embodiments, the substituent meant by “substituted or unsubstituted” is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R901a)(R902a)(R903a), —O—(R904a), —S—(R905a), —N(R906a)(R907a), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms;
R901a to R907a are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms;
when two or more R901a are present, the two or more R901a are mutually the same or different;
when two or more R902a are present, the two or more R902a are mutually the same or different;
when two or more R903a are present, the two or more R903a are mutually the same or different;
when two or more R904a are present, the two or more R904a are mutually the same or different;
when two or more R905a are present, the two or more R905a are mutually the same or different;
when two or more R906a are present, the two or more R906a are mutually the same or different; and
when two or more R907a are present, the two or more R907a are mutually the same or different.
In some embodiments, the substituent meant by “substituted or unsubstituted” is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
In some embodiments, the substituent meant by “substituted or unsubstituted” is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.
The second emitting layer of the organic EL device according to the present exemplary embodiment preferably further contains a fluorescent fourth compound whose main peak wavelength is in a range from 430 nm to 480 nm.
The first emitting layer of the organic EL device according to the present exemplary embodiment preferably further contains a fluorescent third compound whose main peak wavelength is in a range from 430 nm to 480 nm.
The measurement method of the main peak wavelength of the compound is as follows. A toluene solution of a measurement target compound at a concentration ranging from 10−6 mol/L to 10−5 mol/L is prepared and put in a quartz cell. An emission spectrum (ordinate axis: luminous intensity, abscissa axis: wavelength) of the thus-obtained sample is measured at a normal temperature (300K). The emission spectrum is measurable using a spectrophotometer (machine name: F-7000) manufactured by Hitachi High-Tech Science Corporation. It should be noted that the machine for measuring the emission spectrum is not limited to the machine used herein.
A peak wavelength of the emission spectrum, at which the luminous intensity of the emission spectrum is at the maximum, is defined as the main peak wavelength. It should be noted that the main peak wavelength is sometimes referred to as a fluorescence main peak wavelength (FL-peak) herein.
When the first emitting layer of the organic EL device of the present exemplary embodiment contains the first compound and the third compound, the first compound is preferably a host material (sometimes referred to as a matrix material) and the third compound is preferably a dopant material (sometimes referred to as a guest material, emitter, or luminescent material).
When the first emitting layer of the organic EL device of the present exemplary embodiment contains the first and third compounds, a singlet energy S1(H1) of the first compound and a singlet energy S1(D3) of the third compound preferably satisfy a relationship of a numerical formula (Numerical Formula 1) below.
S1(H1)>S1(D3) (Numerical Formula 1)
When the second emitting layer of the organic EL device of the present exemplary embodiment contains the second compound and the fourth compound, the second compound is preferably a host material (sometimes referred to as a matrix material) and the fourth compound is preferably a dopant material (sometimes referred to as a guest material, emitter, or luminescent material).
When the second emitting layer of the organic EL device of the present exemplary embodiment contains the second and fourth compounds, a singlet energy S1(H2) of the second compound and a singlet energy S1(D4) of the fourth compound preferably satisfy a relationship of a numerical formula (Numerical Formula 2) below.
S1(H2)>S1(D4) (Numerical Formula 2)
Singlet Energy S1
A method of measuring the singlet energy Si with use of a solution (occasionally referred to as a solution method) is exemplified by a method below.
A toluene solution of a measurement target compound at a concentration ranging from 10−5 mol/L to 10−4 mol/L is prepared and put in a quartz cell. An absorption spectrum (ordinate axis: absorption intensity, abscissa axis: wavelength) of the thus-obtained sample is measured at a normal temperature (300K). A tangent is drawn to the fall of the absorption spectrum on the long-wavelength side, and a wavelength value λedge (nm) at an intersection of the tangent and the abscissa axis is assigned to a conversion equation (F2) below to calculate singlet energy.
S1 [eV]=1239.85/λedge Conversion Equation (F2)
Any device for measuring absorption spectrum is usable. For instance, a spectrophotometer (U3310 manufactured by Hitachi, Ltd.) is usable.
The tangent to the fall of the absorption spectrum on the long-wavelength side is drawn as follows. While moving on a curve of the absorption spectrum from the maximum spectral value closest to the long-wavelength side in a long-wavelength direction, a tangent at each point on the curve is checked. An inclination of the tangent is decreased and increased in a repeated manner as the curve fell (i.e., a value of the ordinate axis is decreased). A tangent drawn at a point of the minimum inclination closest to the long-wavelength side (except when absorbance is 0.1 or less) is defined as the tangent to the fall of the absorption spectrum on the long-wavelength side.
The maximum absorbance of 0.2 or less is not included in the above-mentioned maximum absorbance on the long-wavelength side.
It is preferable that the first emitting layer and the second emitting layer do not contain a phosphorescent material (dopant material).
Further, it is preferable that the first emitting layer and the second emitting layer do not contain a heavy-metal complex and a phosphorescent rare-earth metal complex. Examples of the heavy-metal complex herein include iridium complex, osmium complex, and platinum complex.
Further, it is also preferable that the first emitting layer and the second emitting layer do not contain a metal complex.
Film Thickness of Emitting Layer
A film thickness of the emitting layer of the organic EL device in the present exemplary embodiment is preferably in a range of 5 nm to 50 nm, more preferably in a range of 7 nm to 50 nm, further preferably in a range of 10 nm to 50 nm. When the film thickness of the emitting layer is 5 nm or more, the formation of the emitting layer and adjustment of chromaticity are likely to be facilitated. When the film thickness of the emitting layer is 50 nm or less, an increase in the drive voltage is likely to be reducible.
Content Ratio of Compound in Emitting Layer
When the first emitting layer contains the first compound and the third compound, the content ratios of the first and third compounds in the emitting layer are, for instance, preferably determined as follows.
The content ratio of the first compound is preferably in a range from 80 mass % to 99 mass %, more preferably in a range from 90 mass % to 99 mass %, further preferably in a range from 95 mass % to 99 mass %.
The content ratio of the third compound is preferably in a range from 1 mass % to 10 mass %, more preferably in a range from 1 mass % to 7 mass %, further preferably in a range from 1 mass % to 5 mass %.
An upper limit of the total of the respective content ratios of the first and third compounds in the first emitting layer is 100 mass %.
It should be noted that the first emitting layer of the present exemplary embodiment may further contain material(s) other than the first and third compounds.
The first emitting layer may include a single type of the first compound or may include two or more types of the first compound. The first emitting layer may include a single type of the third compound or may include two or more types of the third compound.
An example of the organic EL device whose first emitting layer contains mutually different two or more types of first compounds is as follows.
An organic EL device including: an anode; a cathode; a first emitting layer disposed between the anode and the cathode; and a second emitting layer disposed between the first emitting layer and the cathode, in which
the first emitting layer contains a first host material in a form of the first compound including at least one group represented by the formula (11), the first compound being represented by the formula (1),
the first emitting layer contains mutually different two or more types of the first compound,
the second emitting layer contains a second host material in a form of the second compound represented by the formula (2), and
the first emitting layer and the second emitting layer are in direct contact with each other.
When the second emitting layer contains the second compound and the fourth compound, the content ratios of the second and fourth compounds in the second emitting layer are, for instance, preferably determined as follows.
The content ratio of the second compound is preferably in a range from 80 mass % to 99 mass %, more preferably in a range from 90 mass % to 99 mass %, further preferably in a range from 95 mass % to 99 mass %.
The content ratio of the fourth compound is preferably in a range from 1 mass % to 10 mass %, more preferably in a range from 1 mass % to 7 mass %, further preferably in a range from 1 mass % to 5 mass %.
An upper limit of the total of the respective content ratios of the second and fourth compounds in the second emitting layer is 100 mass %.
It should be noted that the second emitting layer of the present exemplary embodiment may further contain material(s) other than the second and fourth compounds.
The second emitting layer may include a single type of the second compound or may include two or more types of the second compound. The second emitting layer may include a single type of the fourth compound or may include two or more types of the fourth compound.
An example of the organic EL device whose second emitting layer contains mutually different two or more types of second compounds is as follows.
An organic EL device including: an anode; a cathode; a first emitting layer disposed between the anode and the cathode; and a second emitting layer disposed between the first emitting layer and the cathode, in which
the first emitting layer contains a first host material in a form of the first compound including at least one group represented by the formula (11), the first compound being represented by the formula (1),
the second emitting layer contains a second host material in a form of the second compound represented by the formula (2),
the second emitting layer contains mutually different two or more types of the second compound; and
the first emitting layer and the second emitting layer are in direct contact with each other.
Arrangement(s) of an organic EL device 1 will be further described below. It should be noted that the reference numerals will be sometimes omitted below.
Substrate
The substrate is used as a support for the organic EL device. For instance, glass, quartz, plastics and the like are usable for the substrate. A flexible substrate is also usable. The flexible substrate refers to a bendable substrate, example of which is a plastic substrate or the like. Examples of the material for the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Moreover, an inorganic vapor deposition film is also usable.
Anode
Metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound and a mixture thereof are preferably used as the anode formed on the substrate. Specific examples of the material include ITO (Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chrome (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of a metal material (e.g., titanium nitride) are usable.
The material is typically formed into a film by a sputtering method. For instance, the indium oxide-zinc oxide can be formed into a film by the sputtering method using a target in which zinc oxide in a range from 1 mass % to 10 mass % is added to indium oxide. Moreover, for instance, the indium oxide containing tungsten oxide and zinc oxide can be formed by the sputtering method using a target in which tungsten oxide in a range from 0.5 mass % to 5 mass % and zinc oxide in a range from 0.1 mass % to 1 mass % are added to indium oxide. In addition, the anode may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method or the like.
Among the organic layers formed on the anode, since the hole injecting layer adjacent to the anode is formed of a composite material into which holes are easily injectable irrespective of the work function of the anode, a material usable as an electrode material (e.g., metal, an alloy, an electroconductive compound, a mixture thereof, and the elements belonging to the group 1 or 2 of the periodic table) is also usable for the anode.
A material having a small work function such as elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, an alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, a rare earth metal such as europium (Eu) and ytterbium (Yb), alloys including the rare earth metal are also usable for the anode. It should be noted that the vacuum deposition method and the sputtering method are usable for forming the anode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the anode, the coating method and the inkjet method are usable.
Cathode
It is preferable to use metal, an alloy, an electroconductive compound, and a mixture thereof, which have a small work function (specifically, 3.8 eV or less) for the cathode. Examples of the material for the cathode include elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, the alkali metal such as lithium (Li) and cesium (Cs), the alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, the rare earth metal such as europium (Eu) and ytterbium (Yb), and alloys including the rare earth metal.
It should be noted that the vacuum deposition method and the sputtering method are usable for forming the cathode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the cathode, the coating method and the inkjet method are usable.
By providing the electron injecting layer, various conductive materials such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide may be used for forming the cathode regardless of the work function. The conductive materials can be formed into a film using the sputtering method, inkjet method, spin coating method and the like.
Hole Injecting Layer
The hole injecting layer is a layer containing a substance exhibiting a high hole injectability. Examples of the substance exhibiting a high hole injectability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chrome oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
In addition, the examples of the highly hole-injectable substance further include: an aromatic amine compound, which is a low-molecule organic compound, such that 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1); and dipyrazino[2,34:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).
In addition, a high polymer compound (e.g., oligomer, dendrimer and polymer) is usable as the substance exhibiting a high hole injectability. Examples of the high-molecule compound include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N, N′-bis(4-butylphenyl)-N, N′-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Moreover, an acid-added high polymer compound such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrene sulfonic acid)(PAni/PSS) are also usable.
Hole Transporting Layer
The hole transporting layer is a layer containing a highly hole-transporting substance. An aromatic amine compound, carbazole derivative, anthracene derivative and the like are usable for the hole transporting layer. Specific examples of a material for the hole transporting layer include 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4″-tris(N, N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above-described substances mostly have a hole mobility of 10−6 cm2/(V·s) or more.
For the hole transporting layer, a carbazole derivative such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA) and an anthracene derivative such as t-BuDNA, DNA, and DPAnth may be used. A high polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) is also usable.
However, in addition to the above substances, any substance exhibiting a higher hole transportability than an electron transportability may be used. It should be noted that the layer containing the substance exhibiting a high hole transportability may be not only a single layer but also a laminate of two or more layers formed of the above substance(s).
Electron Transporting Layer
The electron transporting layer is a layer containing a highly electron-transporting substance. For the electron transporting layer, 1) a metal complex such as an aluminum complex, beryllium complex, and zinc complex, 2) a hetero aromatic compound such as imidazole derivative, benzimidazole derivative, azine derivative, carbazole derivative, and phenanthroline derivative, and 3) a high polymer compound are usable. Specifically, as a low-molecule organic compound, a metal complex such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO and ZnBTZ is usable. In addition to the metal complex, a heteroaromatic compound such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs) is usable. In the exemplary embodiment, a benzimidazole compound is preferably usable. The above-described substances mostly have an electron mobility of 10−6 cm2/(V·s) or more. It should be noted that any substance other than the above substance may be used for the electron transporting layer as long as the substance exhibits a higher electron transportability than the hole transportability. The electron transporting layer may be provided in the form of a single layer or a laminate of two or more layers of the above substance(s).
Specific examples of the compound usable for the electron transporting layer is exemplified by compounds below. It should however be noted that the invention is not limited by the specific examples of the compound.
Moreover, a high polymer compound is usable for the electron transporting layer. For instance, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like are usable.
Electron Injecting Layer
The electron injecting layer is a layer containing a highly electron-injectable substance. Examples of a material for the electron injecting layer include an alkali metal, alkaline earth metal and a compound thereof, examples of which include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). In addition, the alkali metal, alkaline earth metal or the compound thereof may be added to the substance exhibiting the electron transportability in use. Specifically, for instance, magnesium (Mg) added to Alq may be used. In this case, the electrons can be more efficiently injected from the anode.
Alternatively, the electron injecting layer may be provided by a composite material in a form of a mixture of the organic compound and the electron donor. Such a composite material exhibits excellent electron injectability and electron transportability since electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, the above examples (e.g., the metal complex and the hetero aromatic compound) of the substance forming the electron transporting layer are usable. As the electron donor, any substance exhibiting electron donating property to the organic compound is usable. Specifically, the electron donor is preferably alkali metal, alkaline earth metal and rare earth metal such as lithium, cesium, magnesium, calcium, erbium and ytterbium. The electron donor is also preferably alkali metal oxide and alkaline earth metal oxide such as lithium oxide, calcium oxide, and barium oxide. Moreover, a Lewis base such as magnesium oxide is usable. Further, the organic compound such as tetrathiafulvalene (abbreviation: TTF) is usable.
Layer Formation Method(s)
A method for forming each layer of the organic EL device in the third exemplary embodiment is subject to no limitation except for the above particular description. However, known methods of dry film-forming such as vacuum deposition, sputtering, plasma or ion plating and wet film-forming such as spin coating, dipping, flow coating or ink jet printing are applicable.
Film Thickness
The film thickness of the organic layers of the organic EL device in the present exemplary embodiment is not limited unless otherwise specified in the above. In general, since excessively small film thickness is likely to cause defects (e.g. pin holes) and excessively large thickness leads to the necessity of applying high voltage and consequent reduction in efficiency, the thickness of the organic layer of the organic EL device usually preferably ranges from several nanometers to 1 μm.
According to the present exemplary embodiment, an organic electroluminescence device with enhanced luminous efficiency can be provided.
In the organic EL device according to the present exemplary embodiment, the first emitting layer containing the first host material in a form of the first compound represented by the formula (1) or the like and the second emitting layer containing the second host material in a form of the second compound represented by the formula (2) or the like are in direct contact with each other. By thus layering the first emitting layer and the second emitting layer, the generated singlet exitons and the triplet exitons can be efficiently used and, consequently, the luminous efficiency of the organic EL device can be improved.
Electronic Device
An electronic device according to the present exemplary embodiment is installed with any one of the organic EL devices according to the above exemplary embodiment. Examples of the electronic device include a display device and a light-emitting unit. Examples of the display device include a display component (e.g., an organic EL panel module), TV, mobile phone, tablet and personal computer. Examples of the light-emitting unit include an illuminator and a vehicle light.
The scope of the invention is not limited by the above-described exemplary embodiments but includes any modification and improvement as long as such modification and improvement are compatible with the invention.
For instance, only two emitting layers are not necessarily provided, but more than two emitting layers are provided and laminated with each other. When the organic EL device includes a plurality of (more than two) emitting layers, it is only necessary that at least two of the plurality of emitting layers should satisfy the requirements mentioned in the above exemplary embodiments. The rest of the emitting layers is, for instance, a fluorescent emitting layer or a phosphorescent emitting layer with use of emission caused by electron transfer from the triplet excited state directly to the ground state, in some embodiments.
When the organic EL device includes a plurality of emitting layers, these emitting layers are mutually adjacently provided, or form a so-called tandem organic EL device, in which a plurality of emitting units are layered via an intermediate layer.
An example of the organic EL device including three or more emitting layers is as follows.
An organic EL device including: an anode; a cathode; a first emitting layer disposed between the anode and the cathode; and a second emitting layer disposed between the first emitting layer and the cathode, and
a third emitting layer disposed between the anode and the cathode, the third emitting layer not being in direct contact with both of the first emitting layer and the second emitting layer, in which
the first emitting layer contains a first host material in a form of the first compound including at least one group represented by the formula (11), the first compound being represented by the formula (1),
the second emitting layer contains a second host material in a form of the second compound represented by the formula (2), and
the first emitting layer and the second emitting layer are in direct contact with each other.
It is also preferable that the third emitting layer contains the first compound.
It is also preferable that the third emitting layer contains the second compound.
The organic electroluminescence device preferably include an intermediate layer between the third emitting layer and the first emitting layer/the second emitting layer.
The intermediate layer is generally also referred to as an intermediate electrode, intermediate conductive layer, charge generating layer, electron drawing layer, connection layer or intermediate insulative layer.
The intermediate layer is a layer configured to supply electrons to a layer located close to the anode with respect to the intermediate layer and supply holes to a layer located close to the cathode with respect to the intermediate layer. The intermediate layer can be made of a known material. The intermediate layer is may be a single layer, or may be provided by two or more layers. A unit made of two or more intermediate layers is sometimes referred to as an intermediate unit. The compositions of the plurality of intermediate layers of the intermediate unit are mutually the same or different.
Further, a plurality of layers including the emitting layer, which are disposed between the intermediate layer/intermediate unit and the anode/cathode, is sometimes collectively referred to as an emitting unit. Examples of the device arrangement of the organic EL device including a plurality of emitting units include (TND1) to (TND4) below.
(TND1) anode/first light-emitting unit/intermediate layer/second light-emitting unit/cathode
(TND2) anode/first light-emitting unit/intermediate unit/second light-emitting unit/cathode
(TND3) anode/first light-emitting unit/first intermediate layer/second light-emitting unit/second intermediate layer/third emitting unit/cathode
(TND4) anode/first light-emitting unit/first intermediate unit/second light-emitting unit/second intermediate unit/third emitting unit/cathode
The number of the emitting unit and the intermediate layer (or intermediate unit) is not limited to the examples shown above.
It is preferable that the first emitting layer and the second emitting layer are included in at least one of the first light-emitting unit, second light-emitting unit, and the third emitting unit.
It is also preferable that the first emitting layer and the second emitting layer are included in all of the light-emitting units of the organic EL device.
For instance, in some embodiments, a blocking layer is provided adjacent to at least one of a side near the anode and a side near the cathode of the emitting layer. The blocking layer is preferably provided in contact with the emitting layer to block at least any of holes, electrons, and excitons.
For instance, when the blocking layer is provided in contact with the cathode-side of the emitting layer, the blocking layer permits transport of electrons, and blocks holes from reaching a layer provided near the cathode (e.g., the electron transporting layer) beyond the blocking layer. When the organic EL device includes the electron transporting layer, the blocking layer is preferably disposed between the emitting layer and the electron transporting layer.
When the blocking layer is provided in contact with the anode-side of the emitting layer, the blocking layer permits transport of holes, but blocks electrons from reaching a layer provided near the anode (e.g., the hole transporting layer) beyond the blocking layer. When the organic EL device includes the hole transporting layer, the blocking layer is preferably disposed between the emitting layer and the hole transporting layer.
Alternatively, the blocking layer may be provided adjacent to the emitting layer so that the excitation energy does not leak out from the emitting layer toward neighboring layer(s). The blocking layer blocks excitons generated in the emitting layer from being transferred to a layer(s) (e.g., the electron transporting layer and the hole transporting layer) closer to the electrode(s) beyond the blocking layer.
The emitting layer is preferably bonded with the blocking layer.
Specific structure, shape and the like of the components in the invention may be designed in any manner as long as an object of the invention can be achieved.
Compounds
Structures of the compounds represented by the formula (1) in Examples and Reference Examples are as shown below.
Structures of the compounds represented by the formula (2) in Examples and Reference Examples are as shown below.
Structures of other compounds used for production of the organic EL devices according to Comparatives are shown below
Structures of other compounds used for production of the organic EL devices according to Examples, Reference Examples, and Comparatives are shown below.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT2 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 1 is roughly shown as follows.
ITO(130)/HA1(5)/HT1(80)/HT2(10)/BH1:BD1(5,98%:0:2%)/BH2:BD1(20,98%:2%)/ET 1(10)/ET2(15)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage (98%;2%) in the same parentheses respectively indicate a ratio (mass %) of the host material (the compound BH1 or the compound BH2) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
Comparative 1
As shown in Table 1, the organic EL device of Comparative 1 was prepared in the same manner as in Example 1 except that a 25-nm-thick first emitting layer was formed as the emitting layer and the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer.
Comparative 2
As shown in Table 1, the organic EL device of Comparative 2 was prepared in the same manner as in Example 1 except that a 25-nm-thick second emitting layer was formed as the emitting layer on the second hole transporting layer without forming the first emitting layer.
Evaluation of Organic EL Device
The organic EL devices prepared in Examples, Reference Examples, and Comparatives were evaluated in terms of the items below. Evaluation results are shown in Tables 1 to 45.
It should be noted that evaluation results of some Examples and some Comparatives are shown in a plurality of Tables.
External Quantum Efficiency EQE
Voltage was applied on the organic EL devices such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
Lifetime LT90
Voltage was applied on the resultant organic EL devices such that a current density was 50 mA/cm2, where a time (LT90 (unit: hr)) elapsed before a luminance intensity was reduced to 90% of the initial luminance intensity was measured. The results are shown in Table 1.
Lifetime LT95
Voltage was applied on the resultant devices such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured.
It should be noted that the lifetime LT95 of the organic EL devices according to Example 155 and Comparative 124 was measured as a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity after applying voltage on the devices such that a current density was 15 mA/cm2.
Main Peak Wavelength λp when the Device is Driven
Voltage was applied on the organic EL devices such that a current density of the organic EL device was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The main peak wavelength λp (unit: nm) was calculated based on the obtained spectral radiance spectrum.
Drive Voltage
The voltage (unit: V) when electric current was applied between the anode and the cathode such that the current density was 10 mA/cm2 was measured.
As shown in Table 1, the organic EL device according to Example 1, in which the first emitting layer containing the first host material in a form of the first compound and the second emitting layer containing the second host material in a form of the second compound were in direct contact with each other, emitted at a higher luminous efficiency than the organic EL devices according to Comparatives 1 to 2 including only one of the emitting layers. Further, the organic EL device according to Example 1 exhibited longer lifetime than that of organic EL devices according to Comparatives 1 to 2.
The organic EL devices according to Examples 2 to 19 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer was exchanged to the first compounds listed in Table 1.
Comparatives C20, 3 to 21
The organic EL devices according to Comparatives C20 and 3 to 21 were prepared in the same manner as in Comparative 1 except that the compound BH1 (first host material) in the first emitting layer was exchanged to the first compounds listed in Table 3.
The organic EL device according to Example 21 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was exchanged to the compound listed in Table 4.
Comparatives C22 to 23
The organic EL devices according to Comparatives C22 to 23 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were exchanged to the compounds listed in Table 4.
Comparative 22
The organic EL device according to Comparative 22 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 4.
The organic EL device according to Example 24 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 5.
Comparatives C25 to 26
The organic EL devices according to Comparatives C25 to 26 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were replaced with the compounds listed in Table 5.
Comparative 23
The organic EL device according to Comparative 23 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 5.
The organic EL device according to Example 27 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 6.
Comparatives C28 to 29
The organic EL devices according to Comparatives C28 to 29 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were replaced with the compounds listed in Table 6.
Comparative 24
The organic EL device according to Comparative 24 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 6.
The organic EL device according to Example 30 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 7.
Comparatives C31 to 32
The organic EL devices according to Comparatives C31 to 32 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were replaced with the compounds listed in Table 7.
Comparative 25
The organic EL device according to Comparative 25 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 7.
The organic EL device according to Example 33 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 8.
Comparatives C34 to 35
The organic EL devices according to Comparatives C34 to 35 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were replaced with the compounds listed in Table 8.
Comparative 26
The organic EL device according to Comparative 26 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 8.
The organic EL device according to Example 36 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 9.
Comparatives C37 to 38
The organic EL devices according to Comparatives C37 to 38 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were replaced with the compounds listed in Table 9.
Comparative 27
The organic EL device according to Comparative 27 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 9.
The organic EL device according to Example 39 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 10.
Comparatives C40 to 41
The organic EL devices according to Comparatives C40 to 41 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were replaced with the compounds listed in Table 10.
Comparative 28
The organic EL device according to Comparative 28 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was exchanged to the compound listed in Table 10.
The organic EL device according to Example 42 was prepared in the same manner as in Example 1 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 11.
Comparatives C43 to 44
The organic EL devices according to Comparatives C43 to 44 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BH2 (second host material) in the second emitting layer were replaced with the compounds listed in Table 11.
Comparative 29
The organic EL device according to Comparative 29 was prepared in the same manner as in Comparative 2 except that the compound BH2 (second host material) in the second emitting layer was replaced with the compound listed in Table 11.
The organic EL device according to Example 45 was prepared in the same manner as in Example 1 except that the compound BD1 in the first emitting layer and the compound BD1 in the second emitting layer were replaced with the compounds listed in Table 12.
Comparatives C46 to 47
The organic EL devices according to Comparatives C46 to 47 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BD1 in the second emitting layer were replaced with the compounds listed in Table 12.
Comparative 30
The organic EL device according to Comparative 30 was prepared in the same manner as in Comparative 1 except that the compound BD1 in the first emitting layer was replaced with the compound listed in Table 12.
Comparative 31
The organic EL device according to Comparative 31 was prepared in the same manner as in Comparative 2 except that the compound BD1 in the second emitting layer was replaced with the compound listed in Table 12.
The organic EL device according to Example 48 was prepared in the same manner as in Example 1 except that the compound BD1 in the first emitting layer and the compound BD1 in the second emitting layer were replaced with the compounds listed in Table 13.
Comparatives C49 to 50
The organic EL devices according to Comparatives C49 to 50 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer and the compound BD1 in the second emitting layer were replaced with the compounds listed in Table 13.
Comparative 32
The organic EL device according to Comparative 32 was prepared in the same manner as in Comparative 1 except that the compound BD1 in the first emitting layer was replaced with the compound listed in Table 13.
Comparative 33
The organic EL device according to Comparative 33 was prepared in the same manner as in Comparative 2 except that the compound BD1 in the second emitting layer was replaced with the compound listed in Table 13.
The organic EL devices according to Reference Examples 51 to 69 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer was replaced with the compounds listed in Table 14.
Comparatives 34 to 51
The organic EL devices according to Comparatives 34 to 51 were prepared in the same manner as in Comparative 1 except that the compound BH1 (first host material) in the first emitting layer was replaced with the compounds listed in Table 15.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT3 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-21 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET4 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 70 is roughly shown as follows.
ITO(130)/HA1(5)/HT3(80)/HT4(10)/BH1-21:BD1(5.98%:0:2%)/BH2:BD1(20,98%:2%)/ET4(10)/ET2(15)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-21 or the compound BH2) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL devices according to Reference Examples 71 to 78 were prepared in the same manner as in Reference Example 70 except that the compound BH1-21 (first host material) in the first emitting layer was replaced with the first compounds listed in Table 16.
Comparatives 52 to 59
The organic EL devices of Comparatives 52 to 59 were prepared in the same manner as in Reference Example 70 except that a 25-nm-thick first emitting layer was formed as the emitting layer, the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer, and the first compound (first host material) in the first emitting layer was replaced with the first compounds listed in Table 16.
Comparative 60
As shown in Table 16, the organic EL device of Comparative 60 was prepared in the same manner as in Reference Example 70 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT3 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-29 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET3 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 79 is roughly shown as follows.
ITO(130)/HA1(5)/HT3(80)/HT4(10)/BH1-29:BD1(5.98%:0:2%)/BH2:BD1(20,98%:2%)/ET3(10)/ET2(15)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-29 or the compound BH2) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL devices according to Reference Examples 80 to 90 were prepared in the same manner as in Reference Example 79 except that the compound BH1-29 (first host material) in the first emitting layer was replaced with the first compounds listed in Table 17.
Comparatives 61 to 71
The organic EL devices of Comparatives 61 to 71 were prepared in the same manner as in Reference Example 79 except that a 25-nm-thick first emitting layer was formed as the emitting layer, the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer, and the first compound (first host material) in the first emitting layer was replaced with the first compounds listed in Table 17.
Comparative 72
As shown in Table 17, the organic EL device of Comparative 72 was prepared in the same manner as in Reference Example 79 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT5 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratio of the compound HT5 in the hole injecting layer was 97 mass %, and the ratio of the compound HA2 was 3 mass %.
After the formation of the hole injecting layer, the compound HT5 was vapor-deposited to form an 85-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 5-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-61 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET3 was vapor-deposited on the second emitting layer to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET6 and the compound Liq were co-deposited on the first electron transporting layer (HBL) to form a 25-nm-thick electron transporting layer (ET). The ratios of the compound ET6 and the compound Liq in the electron transporting layer (ET) were both 50 mass %. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium((8-Quinolinolato)lithium).
Liq was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 91 is roughly shown as follows.
ITO(130)/HT5:HA2(10,97%:3%)/HT5(85)/HT4(5)/BH1-61:BD1(5,98%:2%)/BH2:BD1(20,98%:2%)/ET3(5)/ET6:Liq(25, 50%:50%)/Liq(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (97%:3%) respectively indicate a ratio (mass %) of the compound HT5 and the compound HA2 in the hole injecting layer. The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-61 or the compound BH2) and the dopant material (the compound BD1) in the first emitting layer or the second emitting layer. The numerals represented by percentage in the same parentheses (50%:50%) respectively indicate a ratio (mass %) of the compound ET6 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
The organic EL devices according to Reference Examples 92 to 95 were prepared in the same manner as in Reference Example 91 except that the compound BH1-61 (first host material) in the first emitting layer was replaced with the first compounds listed in Table 18.
Comparatives 73 to 76
The organic EL devices of Comparatives 73 to 76 were prepared in the same manner as in Reference Example 91 except that a 25-nm-thick first emitting layer was formed as the emitting layer, the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer, and the first compound (first host material) in the first emitting layer was replaced with the first compounds listed in Table 18.
Comparative 77
As shown in Table 18, the organic EL device of Comparative 77 was prepared in the same manner as in Reference Example 91 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT3 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT3 and the compound HA2 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After the formation of the hole injecting layer, the compound HT3 was vapor-deposited to form an 85-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 5-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-75 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET3 was vapor-deposited on the second emitting layer to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET8 and the compound Liq were co-deposited on the first electron transporting layer (HBL) to form a 25-nm-thick electron transporting layer (ET). The ratios of the compound HT5 and the compound Liq in the electron transporting layer (ET) were both 50 mass %. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium((8-Quinolinolato)lithium).
Liq was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 96 is roughly shown as follows.
ITO(130)/HT3:HA2(10,97%:3%)/HT3(85)/HT4(5)/BH1-75:BD1(5,98%:2%)/BH2:BD1(20,98%:2%)/ET3(5)/ET8:Liq(25, 50%:50%)/Liq(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (97%:3%) respectively indicate a ratio (mass %) of the compound HT3 and the compound HA2 in the hole injecting layer. The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-75 or the compound BH2) and the dopant material (the compound BD1) in the first emitting layer or the second emitting layer. The numerals represented by percentage in the same parentheses (50%:50%) respectively indicate a ratio (mass %) of the compound ET8 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
The organic EL device according to Reference Example 97 was prepared in the same manner as in Reference Example 96 except that the compound BH1-75 (first host material) in the first emitting layer was replaced with the first compound listed in Table 19.
Comparative 78
The organic EL device of Comparative 78 was prepared in the same manner as in Reference Example 96 except that a 25-nm-thick first emitting layer was formed as the emitting layer, the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer, and the first compound (first host material) in the first emitting layer was replaced with the first compound listed in Table 19.
Comparative 79
As shown in Table 19, the organic EL device of Comparative 79 was prepared in the same manner as in Reference Example 96 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT5 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratio of the compound HT5 in the hole injecting layer was 97 mass %, and the ratio of the compound HA2 was 3 mass %.
After the formation of the hole injecting layer, the compound HT5 was vapor-deposited to form an 85-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 5-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-64 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET3 was vapor-deposited on the second emitting layer to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET8 and the compound Liq were co-deposited on the first electron transporting layer (HBL) to form a 25-nm-thick electron transporting layer (ET). The ratios of the compound ET8 and the compound Liq in the electron transporting layer (ET) were both 50 mass %.
Liq was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 98 is roughly shown as follows.
ITO(130)/HT5:HA2(10,97%:3%)/HT5(85)/HT4(5)/BH1-64:BD1(5,98%:2%)/BH2:BD1(20,98%:2%)/ET3(5)/ET8:Liq(25, 50%:50%)/Liq(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (97%:3%) respectively indicate a ratio (mass %) of the compound HT5 and the compound HA2 in the hole injecting layer. The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-64 or the compound BH2) and the dopant material (the compound BD1) in the first emitting layer or the second emitting layer. The numerals represented by percentage in the same parentheses (50%:50%) respectively indicate a ratio (mass %) of the compound ET8 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
The organic EL devices according to Reference Examples 99 to 103 were prepared in the same manner as in Reference Example 98 except that the compound BH1-64 (first host material) in the first emitting layer was replaced with the first compounds listed in Table 20.
Comparatives 80 to 84
The organic EL devices of Comparatives 80 to 84 were prepared in the same manner as in Reference Example 98 except that a 25-nm-thick first emitting layer was formed as the emitting layer, the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer, and the first compound (first host material) in the first emitting layer was replaced with the first compound listed in Table 20.
Comparative 85
As shown in Table 20, the organic EL device of Comparative 85 was prepared in the same manner as in Reference Example 98 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT5 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratio of the compound HT5 in the hole injecting layer was 97 mass %, and the ratio of the compound HA2 was 3 mass %.
After the formation of the hole injecting layer, the compound HT5 was vapor-deposited to form an 85-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 5-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-70 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET6 and the compound Liq were co-deposited on the first electron transporting layer (HBL) to form a 25-nm-thick electron transporting layer (ET). The ratios of the compound ET6 and the compound Liq in the electron transporting layer (ET) were both 50 mass %.
Liq was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 104 is roughly shown as follows.
ITO(130)/HT5:HA2(10,97%:3%)/HT5(85)/HT4(5)/BH1-70:BD1(5,98%:2%)/BH2:BD1(20,98%:2%)/ET1(5)/ET6:Liq(25, 50%:50%)/Liq(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (97%:3%) respectively indicate a ratio (mass %) of the compound HT5 and the compound HA2 in the hole injecting layer. The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-70 or the compound BH2) and the dopant material (the compound BD1) in the first emitting layer or the second emitting layer. The numerals represented by percentage in the same parentheses (50%:50%) respectively indicate a ratio (mass %) of the compound ET6 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
The organic EL devices according to Reference Examples 105 to 109 were prepared in the same manner as in Reference Example 104 except that the compound BH1-70 (first host material) in the first emitting layer was replaced with the first compounds listed in Table 21.
Comparatives 86 to 90
The organic EL devices of Comparatives 86 to 90 were prepared in the same manner as in Reference Example 104 except that a 25-nm-thick first emitting layer was formed as the emitting layer, the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer, and the first compound (first host material) in the first emitting layer was replaced with the first compounds listed in Table 21.
Comparative 91
As shown in Table 21, the organic EL device of Comparative 91 was prepared in the same manner as in Reference Example 104 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT8 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-81 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 110 is roughly shown as follows.
ITO(130)/HA1(5)/HT1(80)/HT8(10)/BH1-81:BD1(5,98%:0:2%)/BH2:BD1(20,98%:2%)/ET1(10)/ET2(15)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-81 or the compound BH2) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Reference Example 111 was prepared in the same manner as in Reference Example 110 except that the compound BH1-81 (first host material) in the first emitting layer was replaced with the first compound listed in Table 22.
Comparative 92
The organic EL device of Comparative 92 was prepared in the same manner as in Example 110 except that a 25-nm-thick first emitting layer was formed as the emitting layer and the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer.
Comparative 93
As shown in Table 22, the organic EL device of Comparative 93 was prepared in the same manner as in Reference Example 110 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
The organic EL devices according to Reference Examples 112 to 113 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer was replaced with the compounds listed in Table 23.
Comparative 94
The organic EL device according to Comparative 94 was prepared in the same manner as in Comparative 1 except that the compound BH1 (first host material) in the first emitting layer was replaced with the compound listed in Table 23.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT2 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-83 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET7 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Reference Example 114 is roughly shown as follows.
ITO(130)/HA1(5)/HT1(80)/HT2(10)/BH1-83:BD1(5,98%:2%)/BH2:BD1(20,98%:2%)/ET7(10)/ET2(15)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-83 or the compound BH2) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Reference Example 115 was prepared in the same manner as in Reference Example 114 except that the compound BH1-83 (first host material) in the first emitting layer was replaced with the first compound listed in Table 24.
Comparative 95
The organic EL device of Comparative 95 was prepared in the same manner as in Example 114 except that a 25-nm-thick first emitting layer was formed as the emitting layer and the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer.
Comparative 96
As shown in Table 24, the organic EL device of Comparative 96 was prepared in the same manner as in Reference Example 114 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-8 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 20-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 116 is roughly shown as follows.
ITO(130)/HA1(5)/HT1(80)/HT4(10)/BH1:BD1(5,98%:2%)/BH2-8:BD1(20,98%:2%)/ET1(10)/ET2(20)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1) and the compound BD1 in the first emitting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH2-8) and the compound BD1 in the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Example 117 was prepared in the same manner as in Example 116 except that the compound BH2-8 (second host material) in the second emitting layer was replaced with the second compound listed in Table 25.
Comparative 97
As shown in Table 25, the organic EL device of Comparative 97 was prepared in the same manner as in Example 116 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 25.
The organic EL devices according to Examples 118 to 119 were prepared in the same manner as in Example 116 except that the compound BH2-8 (second host material) in the second emitting layer was replaced with the second compound listed in Table 26.
Comparative 98
As shown in Table 26, the organic EL device of Comparative 98 was prepared in the same manner as in Example 116 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 26.
The organic EL device according to Example 120 was prepared in the same manner as in Example 116 except that the compound BH2-8 (second host material) in the second emitting layer was replaced with the second compound listed in Table 27.
Comparative 99
As shown in Table 27, the organic EL device of Comparative 99 was prepared in the same manner as in Example 116 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 27.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT3 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT4 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1 (first host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-2 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET7 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 20-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 121 is roughly shown as follows.
ITO(130)/HA1(5)/HT3(80)/HT4(10)/BH1:BD2(5,98%:2%)/BH2-2:BD2(20,98%:2%)/ET7(10)/ET2(20)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1) and the compound BD2 in the first emitting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH2-2) and the compound BD2 in the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Example 122 was prepared in the same manner as in Example 121 except that the compound BH2-2 (second host material) in the second emitting layer was replaced with the second compound listed in Table 28.
Comparative 100
As shown in Table 28, the organic EL device of Comparative 100 was prepared in the same manner as in Example 121 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 28.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT5 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT6 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-10 (first host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-2 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET7 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 20-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 123 is roughly shown as follows.
ITO(130)/HA1(5)/HT5(80)/HT6(10)/BH1-10:BD2(5,98%:2%)/BH2-2:BD2(20,98%:2%)/ET7(10)/ET2(20)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-10) and the compound BD2 in the first emitting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH2-2) and the compound BD2 in the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Example 124 was prepared in the same manner as in Example 123 except that the compound BH2-2 (second host material) in the second emitting layer was replaced with the second compound listed in Table 29.
Comparative 101
As shown in Table 29, the organic EL device of Comparative 101 was prepared in the same manner as in Example 123 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 29.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT3 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT7 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-10 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET7 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 20-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 125 is roughly shown as follows.
ITO(130)/HA1(5)/HT3(80)/HT7(10)/BH1-10:BD1(5,98%:2%)/BH2-2:BD1(20,98%:2%)/ET7(10)/ET2(20)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-10) and the compound BD1 in the first emitting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH2-2) and the compound BD1 in the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Example 126 was prepared in the same manner as in Example 125 except that the compound BH2-2 (second host material) in the second emitting layer was replaced with the second compound listed in Table 30.
Comparative 102
As shown in Table 30, the organic EL device of Comparative 102 was prepared in the same manner as in Example 125 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 30.
The organic EL device according to Example 127 was prepared in the same manner as in Example 125 except that the compound BH2-2 (second host material) in the second emitting layer was replaced with the second compound listed in Table 31.
Comparative 103
As shown in Table 31, the organic EL device of Comparative 103 was prepared in the same manner as in Example 125 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 31.
The organic EL device according to Example 128 was prepared in the same manner as in Example 125 except that the compound BH2-2 (second host material) in the second emitting layer was replaced with the second compound listed in Table 32.
Comparative 104
As shown in Table 32, the organic EL device of Comparative 104 was prepared in the same manner as in Example 125 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 32.
The organic EL device according to Example 129 was prepared in the same manner as in Example 125 except that the compound BH2-2 (second host material) in the second emitting layer was replaced with the second compound listed in Table 33.
Comparative 105
As shown in Table 33, the organic EL device of Comparative 105 was prepared in the same manner as in Example 125 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 33.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT3 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT7 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-10 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-8 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET5 was vapor-deposited on the first electron transporting layer to form a 20-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 130 is roughly shown as follows.
ITO(130)/HA1(5)/HT3(80)/HT7(10)/BH1-10:BD1(5,98%:2%)/BH2-8:BD1(20,98%:2%)/ET1(10)/ET5(20)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-10) and the compound BD1 in the first emitting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH2-8) and the compound BD1 in the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Example 131 was prepared in the same manner as in Example 130 except that the compound BH2-8 (second host material) in the second emitting layer was replaced with the second compound listed in Table 34.
Comparative 106
As shown in Table 34, the organic EL device of Comparative 106 was prepared in the same manner as in Example 130 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 34.
The organic EL device according to Example 132 was prepared in the same manner as in Example 130 except that the compound BH2-8 (second host material) in the second emitting layer was replaced with the second compound listed in Table 35.
Comparative 107
As shown in Table 35, the organic EL device of Comparative 107 was prepared in the same manner as in Example 130 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 35.
The organic EL device according to Example 133 was prepared in the same manner as in Example 130 except that the compound BH2-8 (second host material) in the second emitting layer was replaced with the second compound listed in Table 36.
Comparative 108
As shown in Table 36, the organic EL device of Comparative 108 was prepared in the same manner as in Example 130 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 36.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT2 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-8 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET4 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 20-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 134 is roughly shown as follows.
ITO(130)/HA1(5)/HT1(80)/HT2(10)/BH1:BD1(5,98%:2%)/BH2-8:BD1 (20,98%:2%)/ET4(10)/ET2(20)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1) and the compound BD1 in the first emitting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH2-8) and the compound BD1 in the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Example 135 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 37.
Comparative 109
As shown in Table 37, the organic EL device of Comparative 109 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 37.
The organic EL device according to Example 136 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 38.
Comparative 110
As shown in Table 38, the organic EL device of Comparative 110 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 38.
The organic EL device according to Example 137 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 39.
Comparative 111
As shown in Table 39, the organic EL device of Comparative 111 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 39.
The organic EL device according to Example 138 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 40.
Comparative 112
As shown in Table 40, the organic EL device of Comparative 112 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 40.
The organic EL device according to Example 139 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 41.
Comparative 113
As shown in Table 41, the organic EL device of Comparative 113 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 41.
The organic EL device according to Example 140 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 42.
Comparative 114
As shown in Table 42, the organic EL device of Comparative 114 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 42.
The organic EL device according to Example 141 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 43.
Comparative 115
As shown in Table 43, the organic EL device of Comparative 115 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 43.
The organic EL device according to Example 142 was prepared in the same manner as in Example 134 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 44.
Comparative 116
As shown in Table 44, the organic EL device of Comparative 116 was prepared in the same manner as in Example 134 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 44.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HA1 was vapor-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI).
After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT2 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-8 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET7 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 20-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 143 is roughly shown as follows.
ITO(130)/HA1(5)/HT1(80)/HT2(10)/BH1:BD1(5,98%:2%)/BH2-8:BD1 (20,98%:2%)/ET7(10)/ET2(20)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1) and the compound BD1 in the first emitting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH2-8) and the compound BD1 in the second emitting layer. Similar notations apply to the description below.
The organic EL device according to Example 144 was prepared in the same manner as in Example 143 except that the compound BH2-8 (second host material) in the second emitting layer were replaced with the second compound listed in Table 45.
Comparative 117
As shown in Table 45, the organic EL device of Comparative 117 was prepared in the same manner as in Example 143 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, and the second compound (second host material) in the second emitting layer was replaced with the second compound listed in Table 45.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT9 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT9 and the compound HA2 in the hole injecting layer were 90 mass % and 10 mass %, respectively.
After the formation of the hole injecting layer, the compound HT9 was vapor-deposited to form an 85-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT8 was vapor-deposited to form a 5-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1 (first host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-7 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 15-nm-thick second emitting layer.
The compound ET3 was vapor-deposited on the second emitting layer to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET8 and the compound Liq were co-deposited on the first electron transporting layer (HBL) to form a 25-nm-thick second electron transporting layer (ET). The ratios of the compound ET8 and the compound Liq in the second electron transporting layer (ET) were both 50 mass %. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium((8-Quinolinolato)lithium).
Liq was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 145 is roughly shown as follows.
ITO(130)/HT9:HA2(10,90%:10%)/HT9(85)/HT8(5)/BH1:BD2(5,98%:2%)/BH2-7:BD2(15,98%:2%)/ET3(5)/ET8:Liq(25,50%:50%)/Liq(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (90%:10%) respectively indicate a ratio (mass %) of the compound HT9 and the compound HA2 in the hole injecting layer. The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1 or the compound BH2-7) and the dopant material (the compound BD2) in the first emitting layer or the second emitting layer. The numerals represented by percentage in the same parentheses (50%:50%) respectively indicate a ratio (mass %) of the compound ET8 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
Comparative 118
As shown in Table 46, the organic EL device of Comparative 118 was prepared in the same manner as in Example 145 except that a 20-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
Comparative 119
As shown in Table 46, the organic EL device of Comparative 119 was prepared in the same manner as in Example 145 except that a 20-nm-thick first emitting layer was formed as the emitting layer and the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer.
The organic EL devices according to Examples 146 to 147 were prepared in the same manner as in Example 1 except that the compound BH1 (first host material) in the first emitting layer was replaced with the compounds listed in Table 47.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT9 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT9 and the compound HA2 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After the formation of the hole injecting layer, the compound HT9 was vapor-deposited to form a 75-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT10 was vapor-deposited to form a 15-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1 (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 3-nm-thick first emitting layer.
The compound BH2-30 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 17-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 3-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 and the compound Liq were co-deposited on the first electron transporting layer (HBL) to form a 30-nm-thick second electron transporting layer (ET). The ratios of the compound ET2 and the compound Liq in the second electron transporting layer (ET) were 67 mass % and 33 mass %, respectively. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium((8-Quinolinolato)lithium).
LiF and Yb (ytterbium) were co-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer. The ratios of LiF and Yb in the electron injecting layer were both 50 mass %.
Metal Al was vapor-deposited on the electron injecting layer to form an 50-nm-thick cathode.
The device arrangement of the organic EL device in Example 148 is roughly shown as follows.
ITO(130)/HT9:HA2(10,97%:3%)/HT9(75)/HT10(15)/BH1:BD1(3,98%:2%)/BH2-30:BD1(17,98%:2%)/ET1(3)/ET2:Liq(30, 67%:33%)/LiF:Yb(1, 50%:50%)/Al(50)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (97%:3%) respectively indicate a ratio (mass %) of the compound HT9 and the compound HA2 in the hole injecting layer. The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1 or the compound BH2-30) and the dopant material (the compound BD1) in the first emitting layer or the second emitting layer. The numerals represented by percentage in the same parentheses (67%:33%) respectively indicate a ratio (mass %) of the compound ET2 and the compound Liq in the electron transporting layer (ET). The numerals represented by percentage in the same parentheses (50%:50%) respectively indicate a ratio (mass %) of LiF and Yb in the electron injecting layer. Similar notations apply to the description below.
Comparative 120
As shown in Table 48, the organic EL device of Comparative 120 was prepared in the same manner as in Example 148 except that a 20-nm-thick second emitting layer was formed as the emitting layer on the second hole transporting layer without forming the first emitting layer.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT9 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT9 and the compound HA2 in the hole injecting layer were 90 mass % and 10 mass %, respectively.
After the formation of the hole injecting layer, the compound HT9 was vapor-deposited to form an 85-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT8 was vapor-deposited to form a 5-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-85 (first host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-19 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 15-nm-thick second emitting layer.
The compound ET3 was vapor-deposited on the second emitting layer to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET8 and the compound Liq were co-deposited on the first electron transporting layer (HBL) to form a 25-nm-thick electron transporting layer (ET). The ratios of the compound ET8 and the compound Liq in the electron transporting layer (ET) were both 50 mass %. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium((8-Quinolinolato)lithium).
Liq was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 149 is roughly shown as follows.
ITO(130)/HT9:HA2(10,90%:10%)/HT9(85)/HT8(5)/BH1-85:BD2(5, 98%:2%)/BH2-19:BD2(15,98%:2%)/ET3(5)/ET8:Liq(25, 50%:50%)/Liq(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (90%:10%) respectively indicate a ratio (mass %) of the compound HT9 and the compound HA2 in the hole injecting layer. The numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-85 or the compound BH2-19) and the dopant material (the compound BD2) in the first emitting layer or the second emitting layer. The numerals represented by percentage in the same parentheses (50%:50%) respectively indicate a ratio (mass %) of the compound ET8 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
The organic EL device according to Example 150 was prepared in the same manner as in Example 149 except that the compound BH2-19 (second host material) in the second emitting layer was replaced with the second compound listed in Table 49.
Comparative 121
As shown in Table 49, the organic EL device of Comparative 121 was prepared in the same manner as in Example 149 except that a 20-nm-thick first emitting layer was formed as the emitting layer and the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer.
The organic EL devices according to Examples 151 to 152 were prepared in the same manner as in Example 150 except that the compound BH1-85 (first host material) in the first emitting layer was replaced with the compounds listed in Table 50.
An APC (Ag—Pd—Cu) layer (reflective layer) having a film thickness of 100 nm, which was silver alloy layer, and an indium zinc oxide (IZO: registered trademark) film (transparent conductive layer) having a thickness of 10 nm were sequentially formed by sputtering on a glass substrate (25 mm×75 mm×0.7 mm thickness) to be a substrate for preparing a device. Thus, an electrical conductive material layer formed of the APC layer and the IZO film was obtained.
Subsequently, the conductive material layer was patterned by etching using a resist pattern as a mask using a normal lithography technique to form a lower electrode (anode).
Formation of First Light-Emitting Unit
Next, the compound HT9 and the compound HA2 were co-deposited on the lower electrode by vacuum deposition to form a hole injecting layer having a film thickness of 10 nm. The concentrations of the compound HT9 and the compound HA2 in the hole injecting layer were 90 mass % and 10 mass %, respectively.
Next, the compound HT9 was vapor-deposited on the hole injecting layer to form a first hole transporting layer having a thickness of 22 nm.
Next, the compound HT8 was vapor-deposited on the first hole transporting layer to form a second hole transporting layer having a thickness of 5 nm.
The compound BH1 (first host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the second hole transporting layer to form a 3.5-nm-thick first emitting layer (UT1-EM1) of a first light-emitting unit. The concentrations of the compound BH1 and the compound BD2 in the first emitting layer (UT1-EM1) were 99 mass % and 1 mass %, respectively.
The compound BH2-19 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer (UT1-EM1) to form a 13.5-nm-thick second emitting layer (UT1-EM2) of the first light-emitting unit. The concentrations of the compound BH2-19 and the compound BD2 in the second emitting layer (UT1-EM2) were 99 mass % and 1 mass %, respectively.
The compound ET1 was vapor-deposited on the second emitting layer (UT1-EM2) to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
Formation of First Charge Generating Layer
Subsequently, the compound ET8 and Liq were co-deposited on the first electron transporting layer of the first light-emitting unit to form a 25-nm-thick first N layer. The concentrations of the compound ET8 and Liq in the first N layer were both 50 mass %.
Then, the compound ET9 and lithium (Li) were co-deposited on the first N layer to form a 15-nm-thick second N layer. The concentrations of the compound ET9 and Li in the second N layer were 96 mass % and 4 mass %, respectively.
Thereafter, the compound HT9 and the compound HA2 were co-deposited on the second N layer to form a 10-nm-thick first P layer. The concentrations of the compound HT9 and the compound HA2 in the first P layer were 90 mass % and 10 mass %, respectively.
Formation of Second Light-Emitting Unit
Next, the compound HT9 was vapor-deposited on the first P layer to form a 45-nm-thick first hole transporting layer.
Next, the compound HT8 was vapor-deposited on the first hole injecting layer to form a second hole transporting layer having a thickness of 5 nm.
The compound BH1 and the compound BD2 were then co-deposited on the second hole transporting layer to form a 3.5-nm-thick first emitting layer (UT2-EM1) of a second light-emitting unit. The concentrations of the compound BH1 and the compound BD2 in the first emitting layer (UT2-EM1) were 99 mass % and 1 mass %, respectively.
Subsequently, the compound BH2-19 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer (UT2-EM1) to form a 13.5-nm-thick second emitting layer (UT2-EM2) of the second light-emitting unit. The concentrations of the compound BH2-19 and the compound BD2 in the second emitting layer (UT2-EM2) were 99 mass % and 1 mass %, respectively.
Thereafter, the compound ET1 was vapor-deposited on the second emitting layer (UT2-EM2) to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
Formation of Second Charge Generating Layer
Subsequently, the compound ET8 and Liq were co-deposited on the first electron transporting layer of the second light-emitting unit to form a 25-nm-thick third N layer. The concentrations of the compound ET8 and Liq in the third N layer were both 50 mass %.
Then, the compound ET9 and lithium (Li) were co-deposited on the third N layer to form a 15-nm-thick fourth N layer. The concentrations of the compound ET9 and Li in the fourth N layer were 96 mass % and 4 mass %, respectively.
Thereafter, the compound HT9 and the compound HA2 were co-deposited on the fourth N layer to form a 10-nm-thick second P layer. The concentrations of the compound HT9 and the compound HA2 in the second P layer were 90 mass % and 10 mass %, respectively.
Formation of Third Light-Emitting Unit
Subsequently, the compound HT9 was vapor-deposited on the second P layer to form a 35-nm-thick first hole transporting layer on the second P layer.
Next, the compound HT8 was vapor-deposited on the first hole injecting layer to form a second hole transporting layer having a thickness of 5 nm.
The compound BH1 and the compound BD2 were then co-deposited on the second hole transporting layer to form a 3.5-nm-thick first emitting layer (UT3-EM1) of a third light-emitting unit. The concentrations of the compound BH1 and the compound BD2 in the first emitting layer (UT3-EM1) were 99 mass % and 1 mass %, respectively.
Subsequently, the compound BH2-19 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer (UT3-EM1) to form a 13.5-nm-thick second emitting layer (UT3-EM2) of the second light-emitting unit. The concentrations of the compound BH2-19 and the compound BD2 in the second emitting layer (UT3-EM2) were 99 mass % and 1 mass %, respectively.
Thereafter, the compound ET1 was vapor-deposited on the second emitting layer (UT3-EM2) to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
Subsequently, the compound ET8 and Liq were co-deposited on the first electron transporting layer of the third light-emitting unit to form a 38-nm-thick second electron transporting layer. The concentrations of the compound ET8 and Liq in the second electron transporting layer were both 50 mass %.
Thereafter, ytterbium (Yb) was vapor-deposited on the second electron transporting layer of the third light-emitting unit to form a 1.5-nm-thick electron injecting layer.
Then, Mg and Ag were co-deposited on the electron injecting layer of the third light-emitting unit so as to have a mixing ratio (mass % ratio) of 15%:85%, so that an upper electrode (cathode) made of a semi-transparent MgAg alloy (total film thickness 12 nm) was formed.
Next, the compound Cap1 was deposited on the entire surface of the upper electrode to form a capping layer having a thickness of 50 nm.
A top emission organic EL device according to Example 153 was prepared as described above.
A device arrangement of the organic EL device in Example 153 is roughly shown as follows.
APC(100)/IZO(10)/HT9:HA2(10,90%: 10%)/HT9(22)/HT8(5)/BH1:BD2(3.5,99%: 1%)/BH2-19:BD2(13.5,99%: 1%)/ET1(5)/ET8:Liq(25,50%:0:50%)/ET9:Li(15,96%:4%)/HT9:HA2(10, 90%: 10%)/HT9(45)/HT8(5)/BH1:BD2(3.5, 99%: 1%)/BH2-19:BD2(13.5,99%: 1%)/ET1(5)/ET8:Liq(25,50%:0:50%)/ET9:Li(15,96%:4%)/HT9:HA2(10,90%: 10%)/HT9(35)/HT8(5)/BH1:BD2(3.5,99%: 1%)/BH2-19:BD2(13.5,99%: 1%)/ET1(5)/ET8:Liq(38,50%:50%)/Yb(1.5)/Mg:Ag(12,15%:85%)/Cap1(50)
Comparative 122
As shown in Table 51, the top emission organic EL device of Comparative 122 was prepared in the same manner as in Example 153 except that a 17-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer in the first, second and third light-emitting units.
The top emission organic EL device according to Example 154 was prepared in the same manner as Example 153 except that the compound BH2-19 (second host material) in the second emitting layer of the first, second, and third light-emitting units are replaced with the second compound listed in Table 52 and the compound ET1 in the first electron transporting layer is replaced with the compound listed in Table 52.
Comparative 123
As shown in Table 52, the top emission organic EL device of Comparative 123 was prepared in the same manner as in Example 154 except that a 17-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer in the first, second and third light-emitting units.
It should be noted that the values of voltage, EQE and LT95 shown in Tables 51 and 52 are not measured for each of the emitting units but for the entire organic EL device including the first, second, and third light-emitting units.
An APC (Ag—Pd—Cu) layer (reflective layer) having a film thickness of 100 nm, which was silver alloy layer, and an indium zinc oxide (IZO: registered trademark) film (transparent conductive layer) having a thickness of 10 nm were sequentially formed by sputtering on a glass substrate (25 mm×75 mm×0.7 mm thickness) to be a substrate for preparing a device. Thus, a conductive material layer formed of the APC layer and the IZO film was obtained.
Subsequently, the conductive material layer was patterned by etching using a resist pattern as a mask using a normal lithography technique to form a lower electrode (anode).
Next, the compound HT5 and the compound HA2 were co-deposited on the lower electrode by vacuum deposition to form 10-nm-thick hole injecting layer. The concentrations of the compound HT5 and the compound HA2 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
Next, the compound HT5 was vapor-deposited on the hole injecting layer to form a 114-nm-thick first hole transporting layer on the hole injecting layer.
Subsequently, the compound HT4 was vapor-deposited on the first hole injecting layer to form a 5-nm-thick second hole transporting layer.
The compound BH1-85 (first host material (BH)) and the compound BD2 (dopant material (BD)) were then co-deposited on the second hole transporting layer to form a 5-nm-thick first emitting layer. The concentrations of the compound BH1-85 and the compound BD2 in the first emitting layer were 99 mass % and 1 mass %, respectively.
The compound BH2-5 (second host material (BH)) and the compound BD2 (dopant material (BD)) were then co-deposited on the first emitting layer to form a 15-nm-thick second emitting layer. The concentrations of the compound BH2-5 and the compound BD2 in the second emitting layer were 99 mass % and 1 mass %, respectively.
The compound ET3 was then vapor-deposited on the second emitting layer to form a 5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
Subsequently, the compound ET8 and Liq were co-deposited on the first electron transporting layer to form a 25-nm-thick second electron transporting layer. The concentrations of the compound ET8 and Liq in the second electron transporting layer were both 50 mass %.
Then, ytterbium (Yb) was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Next, Mg and Ag were co-deposited on the electron injecting layer so as to have a mixing ratio (mass % ratio) of 10%:90%, so that an upper electrode (cathode) made of a semi-transparent MgAg alloy (total film thickness 12 nm) was formed.
Next, the compound Cap1 was deposited on the entire surface of the upper electrode to form a capping layer having a thickness of 65 nm.
A top emission organic EL device according to Example 156 was prepared as described above.
A device arrangement of the organic EL device in Example 155 is roughly shown as follows.
APC(100)/IZO(10)/HT5:HA2(10,97%:3%)/HT5(114)/HT4(5)/BH1-85:BD2(5,99%:1%)/BH2-5:BD2(15,99%:1%)/ET3(5)/ET8:Liq(25,50%:50%)/Yb(1)/Mg:Ag(12,10%:90%)/Cap1 (65)
Comparative 124
As shown in Table 53, the organic EL device of Comparative 124 was prepared in the same manner as in Example 155 except that the thickness of the first hole transporting layer was changed and a 20-nm-thick second emitting layer was formed on the second hole transporting layer without forming the first emitting layer.
An organic EL device was prepared and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes The film thickness of the ITO transparent electrode was 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, the compound HT1 and the compound HA2 were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA2 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
After the formation of the first hole transporting layer, the compound HT11 was vapor-deposited to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer (EBL)).
The compound BH1-88 (first host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound BH2-3 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET7 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
The device arrangement of the organic EL device in Example 156 is roughly shown as follows.
ITO(130)/HT1:HA2(5,97%:3%)/HT1(80)/HT11(10)/BH1-88:BD2(5, 98%:2%)/BH2-3:BD2(20,98%:2%)/ET7(10)/ET2(15)/LiF(1)/Al(80)
The numerals in parentheses represent film thickness (unit: nm).
The numerals represented by percentage in the same parentheses (97%:3%) respectively indicate a ratio (mass %) of the compound HT1 and the compound HA2 in the hole injecting layer, and numerals represented by percentage in the same parentheses (98%:2%) respectively indicate a ratio (mass %) of the host material (the compound BH1-88 or the compound BH2-3) and the compound BD2 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL devices according to Examples 157 to 158 were prepared in the same manner as in Example 156 except that the compound BH1-88 (first host material) in the first emitting layer was replaced with the second compounds listed in Table 54.
The organic EL device according to Example 159 was prepared in the same manner as in Example 156 except that the compound BH2-3 (second host material) in the second emitting layer was replaced with the second compound listed in Table 54.
The organic EL device according to Example 160 was prepared in the same manner as in Example 159 except that the compound BH1-88 (first host material) in the first emitting layer was replaced with the first compound listed in Table 54.
As shown in Table 54, the organic EL devices of Reference Examples 116 to 118 were prepared in the same manner as in Example 156 except that a 25-nm-thick first emitting layer was formed as the emitting layer, the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer, and the compound BH1-88 (first host material) in the first emitting layer was replaced with the first compounds listed in Table 54.
Comparative 125
As shown in Table 54, the organic EL device of Comparative 125 was prepared in the same manner as in Example 156 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer as the emitting layer without forming the first emitting layer.
Comparative 126
As shown in Table 54, the organic EL device of Comparative 126 was prepared in the same manner as in Example 160 except that a 25-nm-thick first emitting layer was formed as the emitting layer and the first electron transporting layer was formed on the first emitting layer without forming the second emitting layer.
Comparative 127
As shown in Table 54, the organic EL device of Comparative 127 was prepared in the same manner as in Example 160 except that a 25-nm-thick second emitting layer was formed on the second hole transporting layer as the emitting layer without forming the first emitting layer.
Evaluation of Compounds
Preparation of Toluene Solution
The compound BD1 was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution of the compound BD1. Toluene solutions of the compound BD2 and compound BD3 were prepared in the same manner.
Measurement of Fluorescence Main Peak Wavelength (FL-Peak)
Fluorescence main peak wavelength of the toluene solution of the compound BD1 excited at 390 nm was measured using a fluorescence spectrometer (spectrophotofluorometer F-7000 (manufactured by Hitachi High-Tech Science Corporation). The fluorescence main peak wavelengths of the toluene solutions of the compound BD2 and the compound BD3 were measured in the same manner as the compound BD1.
The fluorescence main peak wavelength of the compound BD1 was 453 nm.
The fluorescence main peak wavelength of the compound BD2 was 455 nm.
The fluorescence main peak wavelength of the compound BD3 was 451 nm.
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