Patent Application
20230009458
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 the organic EL device, holes are injected from an anode and electrons are injected from a cathode 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 example, Patent Literature 1). Patent Literature 1 describes an organic electroluminescence device including: an emitting layer containing a pyrene derivative; and a first functional layer laminated on a cathode-side of the emitting layer and containing an anthracene derivative.
The performance of the organic EL device is evaluable in terms of, for instance, luminance, emission wavelength, chromaticity, luminous efficiency, drive voltage, and lifetime.
Patent Literature 1: JP 2019-149408 A
An object of the invention is to provide an organic electroluminescence device that emits light for a long lifetime, and an electronic device including the organic electroluminescence device.
According to an aspect of the invention, there is provided an organic electroluminescence device including: an anode; a cathode; an emitting layer between the anode and the cathode; a first electron transporting layer between the cathode and the emitting layer; and a second electron transporting layer between the cathode and the first electron transporting layer, in which the first electron transporting layer is directly adjacent to the emitting layer, the second electron transporting layer is directly adjacent to the first electron transporting layer, the emitting layer contains a first compound represented by Formula (1) below, the first compound has at least one group represented by Formula (11) below, the first electron transporting layer contains a second compound represented by Formula (2) below, and the second electron transporting layer contains a third compound represented by Formula (3) below.
In Formula (1),
R101 to R110 each independently represent 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 Formula (11),
at least one of R101 to R110 is a group represented by Formula (11),
when a plurality of groups represented by Formula (11) are present, the plurality of groups represented by 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 Formula (11) represents a bonding position to a pyrene ring in Formula (1).
In Formula (2),
R201 to R208 each independently represent 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(R006)(R007), 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 each independently represent 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 each independently represent 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 Formula (3),
Z31, Z32, and Z33 each independently represent a nitrogen atom or CR3,
two or three of Z31, Z32, and Z33 are nitrogen atoms,
R3 is a hydrogen atom, a cyano group, 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 group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), 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 is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms,
B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms,
L is a single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or an (n+1)-valent group having a structure in which two or more mutually different substituted or unsubstituted aromatic hydrocarbon rings are bonded to each other,
C is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,
n is 1, 2, or 3,
when n is 2 or more, L is not a single bond, and
when n is 2 or more, a plurality of C are mutually the same or different.
In the first compound represented by Formula (1), the second compound represented by Formula (2), and the third compound represented by Formula (3), R901, R902, R903, R904, R905, R906, R907, R801, and R802 each independently represent 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.
According to an aspect of the invention, there is provided an electronic device including the organic electroluminescence device according to the aspect of the invention.
According to the aspect of the invention, an organic electroluminescence device that emits light for a long lifetime can be provided. According to the aspect of the invention, an electronic device including the organic electroluminescence device can be provided.
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 deuterium.
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, cross-linking compound, carbon ring compound, and heterocyclic compound) in which the atoms are bonded to 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, cross-linking 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 to a hydrogen atom(s) or a substituent(s) has 6 ring atoms. For instance, the hydrogen atom(s) bonded to carbon atom(s) of a quinazoline ring or the atoms forming a substituent are not counted as the quinazoline ring atoms. Accordingly, a quinazoline ring bonded to 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 do 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.
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.
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) below. (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 an “unsubstituted aryl group” and a “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 further 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 further substituting a hydrogen atom of a substituent of the “substituted aryl group” in the specific example group G1B below.
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, 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.
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 Formulae (TEMP-1) to (TEMP-15) with a substituent.
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 further 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 further 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.
pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazynyl group, pyrimidinyl group, pyrazinyl group, 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.
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.
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 One Hydrogen Atom from Cyclic Structures Represented by Formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):
In 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 or YA is an oxygen atom, a sulfur atom, or NH.
When at least one of XA or YA in Formulae (TEMP-16) to (TEMP-33) is NH or CH2, the monovalent heterocyclic groups derived from the cyclic structures represented by Formulae (TEMP-16) to (TEMP-33) include a monovalent group derived by removing one hydrogen atom from NH or CH2.
(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 biphenylquinazolinyl group.
phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
Groups Obtained 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).
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 further substituting a hydrogen atom of a skeleton of the “substituted alkyl group” in the specific example group G3B, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted alkyl group” in the specific example group G3B.
methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
heptafluoropropyl group (including isomer thereof), pentafluoroethyl group,
2,2,2-trifluoroethyl group, and trifluoromethyl 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 further 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 further substituting a hydrogen atom of a substituent of the “substituted alkenyl group” in the specific example group G4B with a substituent.
vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl 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 a “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.
ethynyl 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 a “substituted or unsubstituted cycloalkyl group,” and a substituted cycloalkyl group refers to a “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 further substituting a hydrogen atom of a substituent of the “substituted cycloalkyl group” in the specific example group G6B with a substituent.
cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
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, and
G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6,
a plurality of G1 in —Si(G1)(G1)(G1) are mutually the same or different,
a plurality of G2 in —Si(G1)(G2)(G2) are mutually the same or different,
a plurality of G1 in —Si(G1)(G1)(G2) are mutually the same or different,
a plurality of G2 in —Si(G2)(G2)(G2) are mutually the same or different,
a plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different, and
a plurality of G6 in —Si(G6)(G6)(G6) are mutually the same or different.
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.
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,
a plurality of G1 in —N(G1)(G1) are mutually the same or different,
a plurality of G2 in —N(G2)(G2) are mutually the same or different,
a plurality of G3 in —N(G3)(G3) are mutually the same or different, and
a plurality of G6 in —N(G6)(G6) are mutually the same or different.
Specific examples (specific example group G11) of “halogen atom” mentioned herein include a fluorine atom, chlorine atom, bromine atom, and iodine atom.
The “substituted or unsubstituted fluoroalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom bonded to at least one of carbon atoms forming an alkyl group in the “substituted or unsubstituted alkyl group” with a fluorine atom, and also includes a group (perfluoro group) derived by substituting all of hydrogen atoms bonded to carbon atoms forming 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 include a group derived by further 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 further 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.
The “substituted or unsubstituted haloalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom bonded to carbon atoms forming the alkyl group in the “substituted or unsubstituted alkyl group” with a halogen atom, and also includes a group derived by substituting all hydrogen atoms bonded to carbon atoms forming 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 include a group derived by further 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 further substituting at least one hydrogen atom of a substituent of the “substituted haloalkyl group” with a substituent. Specific examples of the “unsubstituted 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.
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.
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.
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.
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.
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.
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 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 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.
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.
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.
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 Formulae (TEMP-42) to (TEMP-52), Q1 to Q10 are each independently a hydrogen atom or a substituent.
In Formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
In Formulae (TEMP-53) to (TEMP-62), Q1 to Q10 are each independently a hydrogen atom or a substituent.
In Formulae, Q9 and Q10 may be mutually bonded through a single bond to form a ring.
In Formulae (TEMP-53) to (TEMP-62), * represents a bonding position.
In Formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.
In 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 Formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.
In Formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.
The substituent mentioned herein has been described above.
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 of “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 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 combination of adjacent ones of R921 to R930 (i.e. the combination at issue) is a combination of R921 and R922, a combination of R922 and R923, a combination of R923 and R924, a combination of R924 and R930, a combination of R930 and R925, a combination of R925 and R926, a combination of R926 and R927, a combination of R927 and R928, a combination of R928 and R929, or a combination 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 Formula (TEMP-103) is represented by 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 and 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 Formula (TEMP-103) is represented by Formula (TEMP-105) below. In 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 Formula (TEMP-104) are each independently a “monocyclic ring” or a “fused ring.” Further, the ring QA and the ring QC formed in Formula (TEMP-105) are each a “fused ring.” The ring QA and the ring QC in Formula (TEMP-105) are fused to form a fused ring. When the ring QA in Formula (TMEP-104) is a benzene ring, the ring QA is a monocyclic ring. When the ring QA in Formula (TMEP-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 Formula (TEMP-104) is a ring formed by a carbon atom of the anthracene skeleton bonded to R921, a carbon atom of the anthracene skeleton bonded to 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 to R921, a carbon atom of the anthracene skeleton bonded to 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 of “bonded to form a ring”).
In an exemplary embodiment herein, a substituent for the substituted or unsubstituted group (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 represent 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, a substituent for the substituted or unsubstituted group 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, a substituent for the substituted or unsubstituted group 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 unsaturated 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” represent a range whose lower limit is the value (AA) recited before “to” and whose upper limit is the value (BB) recited after “to.”
An organic electroluminescence device according to the exemplary embodiment includes an anode, a cathode, an emitting layer between the anode and the cathode, a first electron transporting layer between the cathode and the emitting layer, and a second electron transporting layer between the cathode and the first electron transporting layer. The first electron transporting layer is directly adjacent to the emitting layer. The second electron transporting layer is directly adjacent to the first electron transporting layer. The emitting layer contains a first compound represented by Formula (1) below. The first compound has at least one group represented by Formula (11) below. The first electron transporting layer contains a second compound represented by Formula (2) below. The second electron transporting layer contains a third compound represented by Formula (3) below.
The organic EL device according to the exemplary embodiment may include one or more organic layers in addition to the emitting layer and the first and second electron transporting layers. Examples of the organic layer include, for instance, 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.
In the organic EL device according to the exemplary embodiment, the organic layer may consist of the emitting layer and the first and second electron transporting layers. Alternatively, the organic 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, and the electron blocking layer.
Hole Transporting Layer
The organic EL device according to the exemplary embodiment preferably includes a hole transporting layer between the anode and the emitting layer.
An organic EL device 1 includes a light-transmissive substrate 2, an anode 3, a cathode 4, and an organic layer 10 between the anode 3 and the cathode 4. The organic layer 10 includes a hole injecting layer 6, a hole transporting layer 7, an emitting layer 5, a first electron transporting layer 81, a second electron transporting layer 82, and an electron injecting layer 9, which are sequentially laminated on the anode 3.
Emitting Layer
The emitting layer is directly adjacent to the first electron transporting layer. The emitting layer contains the first compound represented by Formula (1) below.
In the organic EL device according to the exemplary embodiment, the first compound is preferably a host material in the emitting layer.
Preferably, the emitting layer of the organic EL device according to the exemplary embodiment contains a fourth compound that fluoresces.
In the organic EL device of the exemplary embodiment, when the emitting layer contains the first compound and the fourth compound, the first compound is preferably a host material (occasionally also referred to as a matrix material) and the fourth compound is preferably a dopant material (occasionally also referred to as a guest material, emitter or a luminescent material).
Herein, the “host material” refers to, for instance, a material that accounts for “50 mass % or more of the layer.” Accordingly, for instance, when the emitting layer contains the first compound represented by Formula (1) below as a host material, the emitting layer contains the first compound in an amount of 50 mass % or more of a total mass of the emitting layer. Alternatively, the “host material” may account for, for instance, 60 mass % or more of the layer, 70 mass % or more of the layer, 80 mass % or more of the layer, 90 mass % or more of the layer, or 95 mass % or more of the layer.
The emitting layer preferably does not contain a phosphorescent material as the dopant material.
Further, the emitting layer preferably does 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.
The emitting layer also preferably does not contain a metal complex.
An emitting layer of an organic EL device according to an exemplary embodiment may be formed by a plurality of emitting layers.
The emitting layer of an organic EL device according to an exemplary embodiment includes, for example, a first emitting layer and a second emitting layer between the first emitting layer and the first electron transporting layer. In this case, the organic EL device includes the first emitting layer, the second emitting layer, the first electron transporting layer, and the second electron transporting layer in this order from the anode, and the second emitting layer is directly adjacent to the first electron transporting layer. Preferably, the first emitting layer is directly adjacent to the second emitting layer.
An organic EL device 1A includes a light-transmissive substrate 2, an anode 3, a cathode 4, and an organic layer 10 between the anode 3 and the cathode 4. The organic layer 10 includes a hole injecting layer 6, a hole transporting layer 7, an emitting layer 5, a first electron transporting layer 81, a second electron transporting layer 82, and an electron injecting layer 9, which are sequentially laminated on the anode 3. The emitting layer 5 further includes a first emitting layer 51 and a second emitting layer 52.
Preferably, the first and second emitting layers each independently further contain a fluorescent compound.
Preferably, the fluorescent compounds contained in the first and second emitting layers are compounds that emit light having a maximum peak wavelength in a range from 430 nm to 480 nm.
The first emitting layer contains the first compound represented by Formula (1) below.
The first emitting layer also preferably contains the fourth compound that fluoresces and the first compound represented by Formula (1). In that case, the first compound in the first emitting layer is preferably a host material (also referred to as a matrix material), and the fourth compound is preferably a dopant material (also referred to as a guest material, emitter, or luminescent material).
The second emitting layer preferably contains a fifth compound. The fifth compound is also preferably an anthracene derivative. The second emitting layer also preferably contains an anthracene derivative as the host material.
The fifth compound is also preferably a compound represented by Formula (2) below. The second emitting layer also preferably contains a compound represented by Formula (2) below as the host material.
The second emitting layer also preferably contains a sixth compound that fluoresces and the fifth compound. In that case, the fifth compound in the second emitting layer is preferably a host material (also referred to as a matrix material), and the sixth compound is preferably a dopant material (also referred to as a guest material, emitter, or luminescent material). The sixth compound that fluoresces and is contained in the second emitting layer can be the same compound as the aforementioned fourth compound. The fourth compound that fluoresces and is contained in the first emitting layer and the sixth compound that fluoresces and is contained in the second emitting layer are mutually the same or different. The fifth compound contained in the second emitting layer can be the same compound as the second compound represented by Formula (2) below. The compound that is represented by Formula (2) and is contained in the second emitting layer as the fifth compound, and the compound that is represented by Formula (2) and is contained in the first electron transporting layer as the second compound are mutually the same or different. When the second emitting layer contains an anthracene derivative or a compound represented by Formula (2) below, the composition of the second emitting layer is different from that of the first electron transporting layer.
More preferably, the first emitting layer contains a pyrene derivative as the host material, and the second emitting layer contains an anthracene derivative as the host material.
Preferably, the first and second emitting layers contain no phosphorescent material as the dopant material.
Further, the first and second emitting layers preferably contain no heavy metal complex and no phosphorescent rare earth metal complex. Examples of the heavy-metal complex herein include iridium complex, osmium complex, and platinum complex.
The first and second emitting layers also preferably contain no metal complex.
The first compound is a compound represented by Formula (1) below. The first compound has at least one group represented by Formula (11) below.
In Formula (1),
R101 to R110 each independently represent 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 Formula (11),
at least one of R101 to R110 is a group represented by Formula (11),
when a plurality of groups represented by Formula (11) are present, the plurality of groups represented by 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 Formula (11) represents a bonding position to a pyrene ring in Formula (1).
In the first compound represented by Formula (1), R901, R902, R903, R904, R905, R906, R907, R801, and R802 each independently represent 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 Ram 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.
Preferably, the group represented by Formula (11) is a group represented by Formula (111) below.
In Formula (111),
X1 is CR123R124, an oxygen atom, a sulfur atom, or NR125,
L111 and L112 each independently represent 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 Formula (11),
R121, R122, R123, R124, and R125 each independently represent 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,
md is 3, and
three R122 are mutually the same or different.
Among positions *1 to *8 of carbon atoms in a cyclic structure represented by Formula (111a) below in a group represented by Formula (111), L111 is bonded to one of the positions *1 to *4, R121 is bonded to each of three positions of the rest of *1 to *4, L112 is bonded to one of the positions *5 to *8, and R122 is bonded to each of three positions of the rest of *5 to *8.
For instance, in a group represented by Formula (111), when L111 is bonded to a carbon atom at a position *2 in the cyclic structure represented by Formula (111a) and L112 is bonded to a carbon atom at a position *7 in the cyclic structure represented by Formula (111a), the group represented by Formula (111) is represented by Formula (111b) below.
In 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 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 exemplary embodiment, the group represented by Formula (111) is preferably a group represented by Formula (111b).
In the organic EL device according to the 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 exemplary embodiment, it is preferable that ma be 0 or 1 and that mb be 0 or 1.
The group represented by Formula (111) in which ma is 0 and mb is 1 is represented by Formula (111c) below.
In Formula (111c), X1, L112, mc, md, Ar101, R121 and R122 each independently represent the same as X1, L112, mc, md, Ar101, R121 and R122 in Formula (111).
In the organic EL device according to the exemplary embodiment, Ar101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the organic EL device of the exemplary embodiment, Ar101 is preferably a substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted phenanthryl group, or substituted or unsubstituted fluorenyl group.
In the organic EL device of the exemplary embodiment, Ar101 is also preferably a group represented by Formula (12), Formula (13), or Formula (14).
In Formulae (12), (13), and (14),
R111 to R120 each independently represent 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 Formulae (12), (13) and (14) represents a bonding position to L101 in Formula (11), or a bonding position to L112 in Formula (111), (111b), or (111c).
It is also preferable that R124 and R125 in Formulae (12), (13) and (14) each independently represent the same as R801 and R802 described above.
The first compound is preferably represented by Formula (101) below.
In Formula (101),
R101 to R120 each independently represent 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.
The compound represented by Formula (101) in which R103 is a bonding position to L101 and R120 is a bonding position to L101 is represented by Formula (101A) below.
In Formula (101A), R101, R102, R104 to R119, L101 and mx respectively represent the same as R101, R102, R104 to R119, L101 and mx in Formula (101).
In the organic EL device of the exemplary embodiment, L101 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
In the organic EL device of the exemplary embodiment, the first compound is preferably represented by Formula (102) below.
In Formula (102),
R101 to R120 each independently represent the same as R101 to R120 of 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 each independently represent 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 each independently represent 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,
md is 3, and
three R122 are mutually the same or different.
In the compound represented by Formula (102), it is preferable that ma is 0, 1, or 2; and mb is 0, 1, or 2.
In the compound represented by Formula (102), it is preferable that ma is 0 or 1 and mb is 0 or 1.
In the organic EL device of the exemplary embodiment, two or more of R101 to R110 are preferably a group represented by Formula (11).
In the organic EL device of the exemplary embodiment, it is preferable that two or more of R101 to R110 are a group represented by 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 exemplary embodiment,
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 Formula (11) is not a substituted or unsubstituted pyrenyl group.
In the organic EL device according to the exemplary embodiment, it is preferable that R101 to R110 not being the group represented by Formula (11) each independently represent 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 exemplary embodiment, it is preferable that R101 to R110 not being the group represented by Formula (11) each independently represent 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 exemplary embodiment, R101 to R110 not being the group represented by Formula (11) each preferably represent a hydrogen atom.
In the organic EL device of the exemplary embodiment, X1 preferably represents CR123R124. For instance, when X1 is CR123R124, the group represented by Formula (111) is represented by Formula (111d) below.
In Formula (111d), L111, L112, ma, mb, ma+mb, Ar101, R121, R122, R123, R124, R125, mc and md represent the same as L111, L112, ma, mb, ma+mb, Ar101, R121, R122, R123, R124, R125, mc and md in Formula (111).
In the organic EL device of the exemplary embodiment, it is preferable that R123 and R124 are not bonded to each other.
In the organic EL device of the exemplary embodiment, at least one of L111 or L112 preferably represents 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.
In the first compound, examples of the substituent for the “substituted or unsubstituted group” also preferably do not include a substituted or unsubstituted pyrenyl group.
In an exemplary embodiment, the first compound is a compound having only one pyrene ring in a molecule (sometimes referred to as a monopyrene compound).
In an exemplary embodiment, the first compound is a compound having only two pyrene rings in a molecule (sometimes referred to as a bispyrene compound).
In the first compound, all groups described as “substituted or unsubstituted” are preferably “unsubstituted” groups.
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 include the following compounds. It should however be noted that the invention is not limited to the specific examples of the first compound.
The fourth compound and the sixth compound each independently represent at least one compound selected from the group consisting of a compound represented by Formula (3A) below, a compound represented by Formula (4) below, a compound represented by Formula (5) below, a compound represented by Formula (6) below, a compound represented by Formula (7) below, a compound represented by Formula (8) below, a compound represented by Formula (9) below, and a compound represented by Formula (10) below.
A compound represented by Formula (3A) will be described below.
In Formula (3A),
at least one combination of adjacent two or more of Ra301, Ra302, Ra303, Ra304, Ra305, Ra306, Ra307, Ra308, Ra309 and Ra310 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 Ra301 to Ra310 is a monovalent group represented by Formula (31A) below,
Ra301 to Ra310 forming neither the monocyclic ring nor the fused ring and not being the monovalent group represented by Formula (31A) each independently represent 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 Formula (31A),
Ara301 and Ara302 each independently represent 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,
La301, La302, and La303 each independently represent 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 a pyrene ring in Formula (3A).
In the fourth and sixth compounds, R901, R902, R903, R904, R905, R906, and R907 each independently represent 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 Formula (3A), two of Ra301 to Ra310 are each preferably a group represented by Formula (31A).
In an exemplary embodiment, the compound represented by Formula (3A) is a compound represented by Formula (33A) below.
In Formula (33A),
Ra311, Ra312, Ra313, Ra314, Ra315, Ra316, Ra317 and Ra318 each independently represent the same as Ra301 to Ra310 in Formula (3A) that are not the monovalent group represented by Formula (31A),
La312, La313, La314, La315, and La316 each independently represent 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
Ara312, Ara313, Ara315, and Ara316 each independently represent 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 Formula (31A), La301 is preferably a single bond, and La302 and La303 are preferably a single bond.
In an exemplary embodiment, the compound represented by Formula (3A) is represented by Formula (34A) or Formula (35A) below.
In Formula (34A,
Ra311 to Ra318 each independently represent the same as Ra301 to Ra310 in Formula (3A) that are not the monovalent group represented by Formula (31A),
La312, La313, La315 and La316 each independently represent the same as La312, La313, La315 and La316 in Formula (33A), and
Ara312, Ara313, Ara315 and Ara316 each independently represent the same as Ara312, Ara313, Ara315 and Ara316 in Formula (33A).
In Formula (35A),
Ra311 to Ra318 each independently represent the same as Ra301 to Ra310 in Formula (3A) that are not the monovalent group represented by Formula (31A), and
Ara312, Ara313, Ara315 and Ara316 each independently represent the same as Ara312, Ara313, Ara315 and Ara316 in Formula (33A).
In Formula (31A), at least one of Ara301 or Ara302 is preferably a group represented by Formula (36A) below.
In Formulae (33A) to (35A), at least one of Ara312 or Ara313 is preferably a group represented by Formula (36A).
In Formulae (33A) to (35A), at least one of Ara315 or Ara316 is preferably a group represented by Formula (36A).
In Formula (36A),
Xa3 represents an oxygen atom or a sulfur atom,
at least one combination of adjacent two or more of Ra321 to Ra327 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,
Ra321, Ra322, Ra323, Ra324, Ra325, Ra326 and Ra327 not forming the monocyclic ring and not forming the fused ring each independently represent 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 La302, La303, La312, La313, La315 or La316.
Xa3 is preferably an oxygen atom.
Preferably, at least one of Ra321 to Ra327 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.
In Formula (31A), Ara301 is preferably a group represented by Formula (36A) and Ara302 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In Formulae (33A) to (35A), Ara312 is preferably a group represented by Formula (36A) and Ara313 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In Formulae (33A) to (35A), Ara315 is preferably a group represented by Formula (36A) and Ara316 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, a compound represented by Formula (3A) is represented by Formula (37A).
In Formula (37A),
Ra311 to Ra318 each independently represent the same as Ra301 to Ra310 in Formula (3A) that are not the monovalent group represented by Formula (31A),
at least one combination of adjacent two or more of Ra321 to Ra327 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 Ra341 to Ra347 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,
Ra321 to Ra327 and Ra341 to Ra347 not forming the monocyclic ring and not forming the fused ring each independently represent 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
Ra331 to Ra335 and Ra351 to Ra355 each independently represent 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 Formula (3A) include compounds shown below.
Compound Represented by Formula (4)
A compound represented by Formula (4) will be described below.
In Formula (4),
Z each independently represent CRa or a nitrogen atom,
A1 ring and A2 ring each independently represent 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 each independently represent 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 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 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, or Rc is preferably a group represented by Formula (4a) below. More preferably, at least two of Ra, Rb, and Rc are each a group represented by Formula (4a).
[Formula 73]
*-L401-Ar401 (4a)
In Formula (4a),
L401 is 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 Formula (4b) below.
In Formula (4b),
L402 and L403 each independently represent 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,
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 each independently represent 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 an exemplary embodiment, the compound represented by Formula (4) is represented by Formula (42) below.
In 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
R401 to R411 neither forming the monocyclic ring nor forming the fused ring each independently represent 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 Formula (4a). More preferably, at least two of R401 to R411 are each a group represented by Formula (4a).
R404 and R411 are each preferably a group represented by Formula (4a).
In an exemplary embodiment, the compound represented by Formula (4) is a compound formed by bonding a moiety represented by Formula (4-1) or Formula (4-2) below to the A1 ring.
Further, in an exemplary embodiment, the compound represented by Formula (42) is a compound formed by bonding the moiety represented by Formula (4-1) or Formula (4-2) to the ring bonded with R404 to R407.
In 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 Formula (4), or bonded to one of R404 to R407 in Formula (42).
In 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 Formula (4), or bonded to one of R404 to R407 in 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.
R421 to R427 and R431 to R438 forming neither the monocyclic ring nor the fused ring each independently represent 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 an exemplary embodiment, the compound represented by Formula (4) is a compound represented by Formula (41-3), Formula (41-4) or Formula (41-5) below.
In Formulae (41-3), (41-4), and (41-5),
A1 ring is as defined for Formula (4),
R421 to R427 each independently represent the same as R421 to R427 in Formula (4-1), and
R440 to R448 each independently represent the same as R401 to R411 in Formula (42).
In an exemplary embodiment, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms for the A1 ring in Formula (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring.
In an exemplary embodiment, a substituted or unsubstituted heterocycle having 5 to 50 ring atoms for the A1 ring in Formula (41-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
In an exemplary embodiment, the compound represented by Formula (4) or Formula (42) is a compound selected from the group consisting of compounds represented by Formulae (461) to (467) below.
In Formulae (461), (462), (463), (464), (465), (466), and (467),
R421 to R427 each independently represent the same as R421 to R427 in Formula (4-1),
R431 to R438 each independently represent the same as R431 to R438 in Formula (4-2),
R440 to R448 and R451 to R454 each independently represent the same as R401 to R411 in Formula (42),
X4 is an oxygen atom, NR801, or C(R802)(R803),
R801, R802, and R803 each independently represent 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 an exemplary embodiment, in the compound represented by 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 or a substituted or unsubstituted fused ring. The compound represented by Formula (42) in the exemplary embodiment is described in detail as a compound represented by Formula (45).
A compound represented by Formula (45) will be described.
In Formula (45)
two or 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 R465 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 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 form a ring at the same time.
At least two rings formed by R461 to R471 are mutually the same or different.
R461 to R471 forming neither the monocyclic ring nor the fused ring each independently represent 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), —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 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 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 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 Formula (45).
Examples of the above cyclic structures in the compound represented by Formula (45) include structures represented by Formulae (451) to (460) below.
In 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
R4501 to R4514 not forming the monocyclic ring and not forming the fused ring each independently represent the same as R461 to R471 in Formula (45).
In 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
R4512 to R4513, R4515 to R4521 and R4522 to R4525 not forming the monocyclic ring and not forming the fused ring, and R4514 each independently represent the same as R461 to R471 in Formula (45).
In Formula (45), it is preferable that at least one of R462, R464, R465, R470 or R471 (preferably, at least one of R462, R465 or 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 Formula (45), (ii) R461 to R471 not forming the cyclic structure in Formula (45), and (iii) R4501 to R4514, R4515 to R4525 in 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 groups represented by Formulae (461) to (464).
In Formulae (461) to (464),
Rd each independently represent 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 each independently represent 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 Formulae (461) to (464), * each independently represents a bonding position to a cyclic structure.
In the fourth and sixth compounds, R901 to R907 represent the same as R901 to R907 as described above.
In an exemplary embodiment, the compound represented by Formula (45) is represented by one of Formulae (45-1) to (45-6) below.
In 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 Formula (45).
In an exemplary embodiment, the compound represented by Formula (45) is represented by one of Formulae (45-7) to (45-12) below.
In 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 Formula (45).
In an exemplary embodiment, the compound represented by Formula (45) is represented by one of formulae (45-13) to (45-21) below.
In 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 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 Formula (461), a group represented by Formula (463), and a group represented by Formula (464).
In an exemplary embodiment, the compound represented by Formula (45) is represented by one of Formulae (45-22) to (45-25) below.
In 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 each independently represent the same as R461 to R471 in Formula (45).
R801, R802, and R803 each independently represent 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 an exemplary embodiment, the compound represented by Formula (45) is represented by Formula (45-26) below.
In 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 Formula (45),
R801, R802, and R803 each independently represent 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.
Specific examples of the compound represented by Formula (4) include compounds shown below. In the specific examples below, Ph represents a phenyl group, and D represents a deuterium atom.
A compound represented by Formula (5) will be described below. The compound represented by Formula (5) corresponds to a compound represented by Formula (41-3) described above.
In 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,
R501 to R507 and R511 to R517 forming neither the monocyclic ring nor the fused ring each independently represent 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,
R521 and R522 each independently represent 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 combination of R501 and R502, a combination of R502 and R503, a combination of R503 and R504, a combination of R505 and R506, a combination of R506 and R507, and a combination of R501, R502, and R503.
In an exemplary embodiment, at least one, preferably two of R501 to R507 and R511 to R517 are each a group represented by —N(R906)(R907).
In an exemplary embodiment, R501 to R507 and R511 to R517 each independently represent 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 an exemplary embodiment, the compound represented by Formula (5) is a compound represented by Formula (52).
In 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,
R531 to R534, R541 to R544 forming neither the monocyclic ring nor the fused ring, and R551 and R552 each independently represent 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 each independently represent 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 an exemplary embodiment, the compound represented by Formula (5) is a compound represented by Formula (53).
In Formula (53), R551, R552 and R561 to R564 each independently represent the same as R551, R552 and R561 to R564 in Formula (52).
In an exemplary embodiment, R561 to R564 in 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 an exemplary embodiment, R521 and R522 in Formula (5) and R551 and R552 in Formulae (52) and (53) are hydrogen atoms.
In an exemplary embodiment, the substituent for “substituted or unsubstituted” in 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 Formula (5) include compounds shown below.
A compound represented by Formula (6) will be described below.
In 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 each independently bonded to the a ring, b ring or c ring to form a substituted or unsubstituted heterocycle, or not bonded thereto 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 structure formed of a boron atom and two nitrogen atoms at the center of 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 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 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 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 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 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 fused 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 an exemplary embodiment, the a ring, b ring and c ring in Formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
In an exemplary embodiment, the a ring, b ring and c ring in Formula (6) are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.
In an exemplary embodiment, R601 and R602 in 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 an exemplary embodiment, the compound represented by Formula (6) is a compound represented by Formula (62) below.
In Formula (62),
R601A is bonded with at least one of R611 or R621 to form a substituted or unsubstituted heterocycle, or not bonded therewith to form no substituted or unsubstituted heterocycle,
R602A is bonded with at least one of R613 or R614 to form a substituted or unsubstituted heterocycle, or not bonded therewith 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 Formula (62) are groups corresponding to R601 and R602 in Formula (6), respectively.
For instance, R601A and R611 are optionally bonded with each other to form a bicyclic (or tri-or-more cyclic) fused 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 fused 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 may be 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 fused 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 an exemplary embodiment, R611 to R621 not contributing 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 an exemplary embodiment, R611 to R621 not contributing 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 an exemplary embodiment, R611 to R621 not contributing to ring formation are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, R611 to R621 not contributing 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 an exemplary embodiment, the compound represented by Formula (62) is a compound represented by Formula (63) below.
In Formula (63),
R631 is bonded with R646 to form a substituted or unsubstituted heterocycle, or not bonded therewith to form no substituted or unsubstituted heterocycle,
R633 is bonded with R647 to form a substituted or unsubstituted heterocycle, or not bonded therewith to form no substituted or unsubstituted heterocycle,
R634 is bonded with R651 to form a substituted or unsubstituted heterocycle, or not bonded therewith to form no substituted or unsubstituted heterocycle,
R641 is bonded with R642 to form a substituted or unsubstituted heterocycle, or not bonded therewith 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 fused 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 fused 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 an exemplary embodiment, R631 to R651 not contributing 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 an exemplary embodiment, R631 to R651 not contributing 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 an exemplary embodiment, R631 to R651 not contributing to ring formation are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, R631 to R651 not contributing 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 an exemplary embodiment, the compound represented by Formula (63) is a compound represented by Formula (63A) below.
In 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 an exemplary embodiment, R661 to R665 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 an exemplary embodiment, R661 to R665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, the compound represented by Formula (63) is a compound represented by Formula (63B) below.
In Formula (63B),
R671 and R672 each independently represent 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 each independently represent 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 an exemplary embodiment, the compound represented by Formula (63) is a compound represented by Formula (63B′) below.
In Formula (63B′), R672 to R675 each independently represent the same as R672 to R675 in Formula (63B).
In an exemplary embodiment, 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 an exemplary embodiment,
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 an exemplary embodiment, the compound represented by Formula (63) is a compound represented by Formula (63C) below.
In Formula (63C),
R681 and R682 each independently represent 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 each independently represent 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 an exemplary embodiment, the compound represented by Formula (63) is a compound represented by Formula (63C′) below.
In Formula (63C′), R683 to R686 each independently represent the same as R683 to R686 in Formula (63C).
In an exemplary embodiment, R681 to R686 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 an exemplary embodiment, R681 to R686 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
The compound represented by 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 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 Formula (6).
A compound represented by Formula (7) will be described below.
In Formula (7),
r ring is a ring represented by Formula (72) or Formula (73), the r ring being fused with adjacent ring(s) at any position(s),
q ring and s ring are each independently a ring represented by Formula (74) and fused with adjacent ring(s) at any position(s),
p ring and t ring are each independently a structure represented by Formula (75) or Formula (76) and fused with adjacent ring(s) at any position(s),
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 each independently represent 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,
each m3 independently represents 0, 1, 2, or 3,
each m4 independently represents 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 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 an exemplary embodiment, in Formula (72) or Formula (73) representing the r ring, m1=0 or m2=0 is satisfied.
In an exemplary embodiment, the compound represented by Formula (7) is represented by any one of Formulae (71-1) to (71-6) below.
In 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 Formula (7).
In an exemplary embodiment, the compound represented by Formula (7) is represented by any one of Formulae (71-11) to (71-13) below.
In 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 Formula (7).
In an exemplary embodiment, the compound represented by Formula (7) is represented by any one of Formulae (71-21) to (71-25) below.
In 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 Formula (7).
In an exemplary embodiment, the compound represented by Formula (7) is represented by any one of Formulae (71-31) to (71-33) below.
In 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 Formula (7).
In an exemplary embodiment, Ar701 and Ar702 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, 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 Formula (7) include compounds shown below.
A compound represented by Formula (8) will be described below.
In Formula (8),
at least one combination of R801 and R802, R802 and R803, or R803 and R804 are mutually bonded to form a divalent group represented by Formula (82) below, or not mutually bonded, and
at least one combination of R805 and R806, R806 and R807, or R807 and R808 are mutually bonded to form a divalent group represented by Formula (83) below, or not mutually bonded.
At least one of R801 to R804 not forming the divalent group represented by Formula (82) or R811 to R814 is a monovalent group represented by Formula (84) below,
at least one of R805 to R808 not forming the divalent group represented by Formula (83) or R821 to R824 is a monovalent group represented by Formula (84) below,
X8 is CR81R82, an oxygen atom, a sulfur atom, or NR809, and a combination of R81 and R82 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
R801 to R808 not forming the divalent group represented by Formula (82) or (83) and not being the monovalent group represented by Formula (84), R811 to R814 and R821 to R824 not being the monovalent group represented by Formula (84), R81 and R82 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring, and R809 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 Formula (84),
A801 and Ar802 each independently represent 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 each independently represent 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 a 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 Formulae (84) represents a bonding position to the cyclic structure represented by Formula (8) or a bonding position to the group represented by Formula (82) or (83).
It is also preferable that at least one combination of R801 and R802, R802 and R803, or R803 and R804 are mutually bonded, and R805 and R806, R806 and R807, and R807 and R808 are not mutually bonded.
It is also preferable that R801 and R802, R802 and R803, and R803 and R804 are not mutually bonded, and at least one combination of R805 and R806, R806 and R807, or R807 and R808 are mutually bonded.
It is also preferable that at least one combination of R801 and R802, R802 and R803, or R803 and R804 are mutually bonded to form a divalent group represented by Formula (82), and at least one combination of R805 and R806, R806 and R807, or R807 and R808 are mutually bonded to form a divalent group represented by Formula (83).
In Formula (8), the positions for the divalent group represented by Formula (82) and the divalent group represented by 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 an exemplary embodiment, the compound represented by Formula (8) is represented by any one of Formulae (81A-1) to (81A-3) below.
In Formulae (81A-1) to (81A-3),
X8 represents the same as X8 in Formula (8),
at least one of R803, R804, or R811 to R814 in Formula (81A-1) is a monovalent group represented by Formula (84),
at least one of R801, R804, or R811 to R814 in Formula (81A-2) is a monovalent group represented by Formula (84),
at least one of R801, R802, or R811 to R814 in Formula (81A-3) is a monovalent group represented by Formula (84),
at least one of R805 to R808 in Formulae (81A-1) to (81A-3) is a monovalent group represented by Formula (84), and
R801 to R808 and R811 to R814 not being the monovalent group represented by 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 an exemplary embodiment, the compound represented by Formula (8) is represented by any one of Formulae (81-1) to (81-6) below.
In Formulae (81-1) to (81-6),
X8 represents the same as X8 in Formula (8),
at least two of R801 to R824 are each a monovalent group represented by Formula (84), and
R801 to R824 that are not the monovalent group represented by 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 an exemplary embodiment, the compound represented by Formula (8) is represented by any one of Formulae (81-7) to (81-18) below.
In Formulae (81-7) to (81-18),
X8 represents the same as X8 in Formula (8),
* is a single bond to be bonded with the monovalent group represented by Formula (84); and
R801 to R824 each independently represent the same as R801 to R824 in Formulae (81-1) to (81-6) that are not the monovalent group represented by Formula (84).
R801 to R808 not forming the divalent group represented by Formula (82) or (83) and not being the monovalent group represented by Formula (84), and R811 to R814 and R821 to R824 not being the monovalent group represented by 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 Formula (84) is preferably represented by Formula (85) or (86) below.
In Formula (85),
R831 to R840 each independently represent 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 Formula (85) represents the same as * in Formula (84).
In Formula (86),
Ar801, L801, and L803 represent the same as Ar801, L801, and L803 in Formula (84); and
HAr801 is a moiety represented by Formula (87) below.
In 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 Formula (8) include compounds shown below as well as the compounds disclosed in WO 2014/104144.
A compound represented by Formula (9) will be described below.
In 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, and
at least one of A91 ring or A92 ring is bonded with * in a structure represented by Formula (92) below.
In 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 not forming the monocyclic ring and not forming the fused ring, and R93 to R99 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 structure represented by 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 an exemplary embodiment are bonded to the bonds * in the structure represented by 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 an exemplary embodiment are bonded to the bonds * in the structure represented by Formula (92).
In an exemplary embodiment, the group represented by Formula (93) below is bonded to one or both of the A91 ring and A92 ring.
In 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 each independently represent 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 a 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 Formula (93) represents a bonding position to one of A91 ring and A92 ring.
In an exemplary embodiment, 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 structure represented by Formula (92). In this case, the structures represented by Formula (92) may be mutually the same or different.
In an exemplary embodiment, R91 and R92 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, R91 and R92 are mutually bonded to form a fluorene structure.
In an exemplary embodiment, 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 an exemplary embodiment, 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 an exemplary embodiment, X9 is an oxygen atom or a sulfur atom.
Specific examples of the compound represented by Formula (9) include compounds shown below.
A compound represented by Formula (10) will be described below.
In Formula (10),
Ax1 ring is a ring represented by Formula (10a) and fused with adjacent ring(s) at any position(s),
Ax2 ring is a ring represented by Formula (10b) and fused with adjacent ring(s) at any position(s),
two * in 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 and mx2 is 2,
a plurality of R1001 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, a plurality of Ar1001 are mutually the same or different.
In an exemplary embodiment, Ar1001 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, 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 an exemplary embodiment, R1003 and R1004 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, ax is 1.
Specific examples of the compound represented by Formula (10) include compounds shown below.
In an exemplary embodiment, the emitting layer contains, as the fourth compound or the sixth compound, at least one compound selected from the group consisting of a compound represented by Formula (4), a compound represented by Formula (5), a compound represented by Formula (7), a compound represented by Formula (8), a compound represented by Formula (9), and a compound represented by Formula (63a) below.
In Formula (63a),
R631 is bonded with R646 to form a substituted or unsubstituted heterocycle, or not bonded therewith to form no substituted or unsubstituted heterocycle,
R633 is bonded with R647 to form a substituted or unsubstituted heterocycle, or not bonded therewith to form no substituted or unsubstituted heterocycle,
R634 is bonded with R651 to form a substituted or unsubstituted heterocycle, or not bonded therewith to form no substituted or unsubstituted heterocycle,
R641 is bonded with R642 to form a substituted or unsubstituted heterocycle, or not bonded therewith 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 is 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 an exemplary embodiment, the compound represented by Formula (4) is a compound represented by Formula (41-3), Formula (41-4) or Formula (41-5), the A1 ring in 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 an exemplary embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in 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 fused 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 an exemplary embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in 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 fused 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 an exemplary embodiment, the compound represented by Formula (4) is selected from the group consisting of a compound represented by Formula (461) below, a compound represented by Formula (462) below, a compound represented by Formula (463) below, a compound represented by Formula (464) below, a compound represented by Formula (465) below, a compound represented by Formula (466) below, and a compound represented by Formula (467) below.
In Formulae (461) to (467),
at least one combination of adjacent two or more of 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 each independently represent 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 an exemplary embodiment, R421 to R427 and R440 to R448 each independently represent 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 an exemplary embodiment, 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 an exemplary embodiment, the compound represented by Formula (41-3) is a compound represented by Formula (41-3-1) below.
In 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 Formula (41-3).
In an exemplary embodiment, the compound represented by Formula (41-3) is represented by Formula (41-3-2) below.
In 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 Formula (41-3), and at least one of R421 to R427 or R440 to R446 is a group represented by —N(R906)(R907).
In an exemplary embodiment, two of R421 to R427 and R440 to R446 in Formula (41-3-2) are each a group represented by —N(R906)(R907).
In an exemplary embodiment, the compound represented by Formula (41-3-2) is a compound represented by Formula (41-3-3) below.
In 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
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 an exemplary embodiment, the compound represented by Formula (41-3-3) is a compound represented by Formula (41-3-4) below.
In 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 Formula (41-3-3).
In an exemplary embodiment, RA, RB, RC, and RD are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
In an exemplary embodiment, RA, RB, RC, and RD are each independently a substituted or unsubstituted phenyl group.
In an exemplary embodiment, R447 and R448 are each a hydrogen atom.
In an exemplary embodiment, the substituent for “substituted or unsubstituted” group in each of the formulae 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 each independently represent 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 Ra904a 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 an exemplary embodiment, the substituent for “substituted or unsubstituted” group in each of the formulae 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 an exemplary embodiment, the substituent for “substituted or unsubstituted” group in each of the formulae 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.
In the organic EL device according to the exemplary embodiment, the fourth compound is preferably a compound that emits light having a maximum peak wavelength in a range from 430 nm to 480 nm.
In the organic EL device according to the exemplary embodiment, the sixth compound is preferably a compound that emits light having a maximum peak wavelength in a range from 430 nm to 480 nm.
A measurement method of the maximum peak wavelength of a 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 exhibiting the maximum luminous intensity is defined as the maximum peak wavelength. Herein, the maximum peak wavelength of fluorescence is sometimes referred to as the maximum fluorescence peak wavelength (FL-peak).
In the fourth and sixth compounds, all groups described as “substituted or unsubstituted” groups are preferably “unsubstituted” groups.
In the organic EL device of the exemplary embodiment, when the emitting layer contains the first compound and the fourth compound, a singlet energy S1(H1) of the first compound and a singlet energy S1(D4) of the fourth compound preferably satisfy a relationship of a numerical formula (Numerical Formula 1) below.
S
1(H1)>S1(D4) (Numerical Formula 1)
In the organic EL device of the exemplary embodiment, when the emitting layer contains the fifth compound and the sixth compound, a singlet energy S1(H5) of the fifth compound and a singlet energy S1(D6) of the sixth compound preferably satisfy a relationship of a numerical formula (Numerical Formula 1A) below.
S
1(H5)>S1(D6) (Numerical Formula 1A)
Singlet Energy S1
A method of measuring a singlet energy S1 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 (300 K). 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.
S
1 [eV]=1239.85/λedge Conversion Formula (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 in a long-wavelength direction from the local maximum closest to the long-wavelength side among the local maximums of the absorption spectrum, 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 falls (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 local maximum absorbance of 0.2 or less is not included in the above-mentioned local maximum absorbance closet to the long-wavelength side.
A film thickness of the emitting layer of the organic EL device in the exemplary embodiment is preferably in a range from 5 nm to 50 nm, more preferably in a range from 7 nm to 50 nm, further preferably in a range from 10 nm to 50 nm. When the film thickness of the emitting layer is 5 nm or more, the emitting layer is easily formable and chromaticity is easily adjustable. When the film thickness of the emitting layer is 50 nm or less, a rise of the drive voltage is easily suppressible.
When the emitting layer contains the first compound and the fourth compound, a content ratio of each of the first compound and the fourth compound in the emitting layer preferably falls, for instance, within a range below.
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 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 %.
The upper limit of the total of the content ratios of the first compound and the fourth compound in the emitting layer is 100 mass %.
It is not excluded that the emitting layer of the exemplary embodiment further contains a material(s) other than the first and fourth compounds.
The emitting layer may include a single type of the first compound or may include two or more types of the first compound. The emitting layer may include a single type of the fourth compound or may include two or more types of the fourth compound.
The content ratios of first and fourth compounds described above also apply to a case where the first emitting layer contains first and fourth compounds.
It is not excluded that the first emitting layer of the exemplary embodiment further contains a material(s) other than the first and fourth 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 fourth compound or may include two or more types of the fourth compound.
When the second emitting layer contains the fifth and sixth compounds, a content ratio of each of the fifth and sixth compounds in the second emitting layer preferably falls, for instance, within a range below.
The content ratio of the fifth 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 sixth 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 %.
The upper limit of the total of the content ratios of the fifth compound and the sixth compound in the second emitting layer is 100 mass %.
It is not excluded that the second emitting layer of the exemplary embodiment further contains a material(s) other than the fifth and sixth compounds.
The second emitting layer may include a single type of the fifth compound or may include two or more types of the fifth compound. The second emitting layer may include a single type of the sixth compound or may include two or more types of the sixth compound.
In the organic EL device of the exemplary embodiment, the first electron transporting layer is directly adjacent to the emitting layer. The first electron transporting layer contains the second compound represented by Formula (2) below.
The second compound represented by Formula (2) according to the exemplary embodiment will be described.
In Formula (2),
R201 to R208 each independently represent 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 each independently represent 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 each independently represent 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 exemplary embodiment, R901, R902, R903, R904, R905, R906, R907, R801, and R802 each independently represent 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 of the 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 each independently represent 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 each independently represent 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 of the exemplary embodiment, it is preferable that L201 and L202 each independently represent a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and
Ar201 and Ar202 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the organic EL device of the exemplary embodiment, it is preferable that Ar201 and Ar202 each independently represent a phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, diphenylfluorenyl group, dimethylfluorenyl group, benzodiphenylfluorenyl group, benzodimethylfluorenyl group, dibenzofuranyl group, dibenzothienyl group, naphthobenzofuranyl group, or naphthobenzothienyl group.
In the organic EL device of the exemplary embodiment, the second compound represented by Formula (2) is preferably a compound represented by Formula (201), Formula (202), Formula (203), Formula (204), Formula (205), Formula (206), Formula (207), Formula (208), Formula (209) or Formula (210).
In Formulae (201) to (210),
L201 and Ar201 represent the same as L201 and Ar201 in Formula (2), and
R201 to R208 each independently represent the same as R201 to R208 in Formula (2).
It is also preferable that the second compound represented by Formula (2) is a compound represented by Formula (221), Formula (222), Formula (223), Formula (224), Formula (225), Formula (226), Formula (227), Formula (228), or
Formula (229) below.
In 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 Formula (2),
L201 and Ar201 represent the same as L201 and Ar201 in Formula (2),
L203 represents the same as L201 in Formula (2),
L203 and L201 are mutually the same or different,
Ar203 represents the same as Ar201 in Formula (2), and
Ar203 and Ar201 are mutually the same or different.
The second compound represented by Formula (2) is also preferably a compound represented by Formula (241), (242), (243), (244), (245), (246), (247), (248) or (249).
In 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 Formula (2),
L201 and Ar201 represent the same as L201 and Ar201 in Formula (2),
L203 represents the same as L201 in Formula (2),
L203 and L201 are mutually the same or different,
Ar203 represents the same as Ar201 in Formula (2), and
Ar203 and Ar201 are mutually the same or different.
In the second compound represented by Formula (2), R201 to R208 that are not represented by Formula (21) 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, 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 preferably a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.
In the organic EL device according to the exemplary embodiment, it is preferable that R201 to R208 in the second compound represented by Formula (2) 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, or a group represented by —Si(R901)(R902)(R903).
In the organic EL device according to the exemplary embodiment, R201 to R208 in the second compound represented by 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 exemplary embodiment, the first electron transporting layer preferably consists of the 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 include the following compounds. It should however be noted that the invention is not limited to the specific examples of the second compound.
In the organic EL device of the exemplary embodiment, the second electron transporting layer is directly adjacent to the first electron transporting layer. The second electron transporting layer contains the third compound represented by Formula (3) below.
The third compound represented by Formula (3) will be described.
In Formula (3),
Z31, Z32, and Z33 each independently represent a nitrogen atom, or CR3,
two or three of Z31, Z32, and Z33 are nitrogen atoms,
R3 is a hydrogen atom, a cyano group, 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 group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), 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 is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms,
B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms,
L is a single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or a (n+1)-valent group having a structure in which two or more different substituted or unsubstituted aromatic hydrocarbon rings are bonded to each other,
C is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,
n is 1, 2, or 3,
when n is 2 or more, L is not a single bond, and
when n is 2 or more, a plurality of C are mutually the same or different.
In the third compound represented by Formula (3), R901, R902, R903, R904, R905, R906, R907, R801, and R802 each independently represent 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 of the exemplary embodiment, the third compound is preferably a compound represented by Formula (37).
In Formula (37),
A, B and L represent the same as A, B and L defined in Formula (3),
Z31, Z32, and Z33 represent the same as Z31, Z32, and Z33 in Formula (3),
Cz is a group represented by Formula (Cz1), (Cz2), or (Cz3),
n is 1, 2, or 3, and
when n is 2 or 3, a plurality of Cz are mutually the same or different.
In Formulae (Cz1), (Cz2), and (Cz3),
at least one combination of adjacent two or more of R311 to R318 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 R320 to R324 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 R330 to R334 and RX 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 R340 to R344 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 R351 to R358 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,
R311 to R318, R320 to R324, R330 to R334, RX, R340 to R344 and R351 to R358 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, 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 group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), 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,
n1, n2, and n3 are 3;
three R320 are mutually the same or different,
three R330 are mutually the same or different,
three R340 are mutually the same or different,
* in the formulae (Cz1), (Cz2), and (Cz3) is bonded to L, and
R901, R902, R903, and R904 represent the same as R901, R902, R903, and R904 in Formula (3).
In the organic EL device of the exemplary embodiment, the third compound is preferably a compound represented by Formula (37).
In Formula (371),
A, B and L represent the same as A, B and L defined in Formula (3),
Cz represents the same as Cz defined in Formula (3),
n is 1, 2, or 3, and
when n is 2 or 3, a plurality of Cz are mutually the same or different.
In the organic EL device according to the exemplary embodiment, the third compound is preferably a compound represented by Formula (372) below.
In Formula (372),
A and B represent the same as A and B defined in Formula (3),
Z31, Z32, and Z33 represent the same as Z31, Z32, and Z33 defined in Formula (3),
Cza and Czb each independently represent a group represented by Formula (Cz1), (Cz2), or (Cz3), and
L is a single bond, a substituted or unsubstituted trivalent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted trivalent heterocyclic group having 5 to 13 ring atoms, or a trivalent group having a structure in which two or more different substituted or unsubstituted aromatic hydrocarbon rings are bonded to each other.
In the organic EL device according to the exemplary embodiment, L is preferably a single bond, or a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 12 ring carbon atoms.
In the organic EL device according to the exemplary embodiment, the third compound is preferably a compound represented by Formula (36) below.
In Formula (36),
A, B, and C represent the same as A, B, and C defined in Formula (3),
Z31, Z32, and Z33 represent the same as Z31, Z32, and Z33 defined in Formula (3),
at least one combination of adjacent two or more of R32 to R39 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,
R32 to R39 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, 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 group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), 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
R901, R902, R903, and R904 represent the same as R901, R902, R903, and R904 defined in Formula (3).
In the organic EL device according to the exemplary embodiment, the third compound is preferably a compound represented by Formula (361) below.
In Formula (361),
A and B represent the same as A and B defined in Formula (3),
Z31, Z32, and Z33 represent the same as Z31, Z32, and Z33 defined in Formula (3),
R32 to R39 represent the same as R32 to R39 defined in Formula (36),
at least one combination of adjacent two or more of R360 to R364 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,
a combination of R369 and R370 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,
R360 to R364, R369, and R370 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, 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 group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), 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,
R901, R902, R903, and R904 represent the same as R901, R902, R903, and R904 defined in Formula (3), and
n4 is 3, and three R360 are mutually the same or different.
In the organic EL device according to the exemplary embodiment, C is preferably a substituted or unsubstituted aryl group having 13 to 24 ring carbon atoms.
In the organic EL device according to the exemplary embodiment, A is preferably a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
In the organic EL device according to the exemplary embodiment, A is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
In the organic EL device according to the exemplary embodiment, A is preferably a phenyl group, a biphenyl group, or a naphthyl group.
In the organic EL device according to the exemplary embodiment, B is preferably a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
In the organic EL device according to the exemplary embodiment, B is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
In the organic EL device according to the exemplary embodiment, the third compound preferably has no substituted or unsubstituted pyridine ring in a molecule.
In the organic EL device according to the exemplary embodiment, the third compound preferably has no substituted or unsubstituted imidazole ring in a molecule.
In the organic EL device according to the exemplary embodiment, the second electron transporting layer preferably consists of the third compound.
The third compound can be manufactured by a known method. Moreover, the third 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 third compound include the following compounds. It should however be noted that the invention is not limited to the specific examples of the third compound.
In the organic EL device according to the exemplary embodiment, the substituent for “substituted or unsubstituted” group is preferably at least one group 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.
In the organic EL device according to the exemplary embodiment, the substituent for “substituted or unsubstituted” group is preferably an alkyl group having 1 to 5 carbon atoms.
Arrangement(s) of the organic EL device will be further described below. It should be noted that the reference numerals will be sometimes omitted below.
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 is a bendable substrate, which is exemplified by a plastic substrate. 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.
Metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more) is 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.
It is preferable to use metal, an alloy, an electroconductive compound, a mixture thereof, or the like having 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.
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[2,3-f: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.
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).
The organic EL device according to the exemplary embodiment may further include an additional electron transporting layer (e.g., a third electron transporting layer) between the second electron transporting layer and the cathode.
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 heteroaromatic 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-quinolinato)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 for the additional electron transporting layer. The above-described substances mostly have an electron mobility of 10−6 cm2/Vs 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.
Further, 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 cathode.
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 heteroaromatic 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.
A method for forming each layer of the organic EL device in the 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 are applicable.
A film thickness of each of the organic layers of the organic EL device in the exemplary embodiment is not limited unless otherwise specified in the above. In general, the thickness preferably ranges from several nanometers to 1 μm because 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 organic electroluminescence device of the exemplary embodiment preferably emits light having a maximum peak wavelength in a range from 430 nm to 480 nm when the organic electroluminescence device is driven.
The maximum peak wavelength of the light emitted from the organic EL device when being 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 obtained spectral radiance spectrum is at the maximum, is measured and defined as a maximum peak wavelength (unit: nm).
According to the exemplary embodiment, an organic electroluminescence device that emits light for a long lifetime can be provided.
In the organic EL device according to the exemplary embodiment, an emitting layer containing the first compound represented by Formula (1) or the like, the first electron transporting layer containing the second compound represented by Formula (2) or the like, and the second electron transporting layer containing the third compound represented by Formula (3) or the like are in direct contact with each other. Injection of electrons into the first electron transporting layer is reduced appropriately by laminating the emitting layer, the first electron transporting layer, and the second electron transporting layers as described above. As a result, the organic EL device according to the exemplary embodiment has a longer lifetime than known organic EL devices using the second electron transporting layer that contains a pyridine derivative or imidazole derivative.
An electronic device according to a second 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 device. 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 device include an illuminator and a vehicle light.
The scope of the invention is not limited to 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, the emitting layer is not limited to a single layer, but may be provided by laminating two or more emitting layers. When the organic EL device has two or more emitting layers, it is only required that at least one of the emitting layers satisfies the conditions described in the above exemplary embodiments. For instance, the rest of the emitting layers may be 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.
When the organic EL device includes a plurality of emitting layers, these emitting layers may be mutually adjacently provided, or may form a so-called tandem organic EL device in which a plurality of emitting units are layered via an intermediate layer.
Further, for instance, a blocking layer may be provided adjacent to a side of the emitting layer close to the anode. The blocking layer provided at the side of the emitting layer close to the anode is preferably in direct contact with the emitting layer. The blocking layer provided at the side of the emitting layer close to the anode preferably blocks at least one of electrons or excitons.
For instance, when the blocking layer is provided in contact with the side of the emitting layer close to the anode, the blocking layer permits transport of holes and blocks electrons from reaching a layer provided closer to 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 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.
The invention will be described in further detail with reference to Example(s). It should be noted that the scope of the invention is by no means limited to Examples.
Structures of compounds represented by Formula (1) and used for manufacturing organic EL devices in Examples 1 to 8 are shown below.
Structures of compounds represented by Formula (2) and used for manufacturing organic EL devices in Examples 1 to 8 are shown below.
Structures of compounds represented by Formula (3) and used for manufacturing organic EL devices in Examples 1 to 8 are shown below.
Structures of other compounds used for manufacturing organic EL devices in Examples 1 to 8 and Comparative Examples 1 to 8 are shown below.
The organic EL devices were manufactured 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, a compound HT1 and a compound HA1 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. The ratios of the compound HT1 and the compound HA1 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 second hole transporting layer.
After the formation of the second hole transporting layer, a compound HT2 was vapor-deposited to form a 10-nm-thick first hole transporting layer.
A compound PY1 (host material) and a compound BD1 (dopant material (BD)) were co-deposited on the first hole transporting layer such that the ratio of the compound BD1 accounted for 4 mass %, thereby forming a 12.5-nm-thick emitting layer.
A compound AN1 was vapor-deposited on the emitting layer to form a 12.5-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
A compound ET1 was vapor-deposited on the first electron transporting layer to form a 10-nm-thick second electron transporting layer (ET).
A compound ET3 was vapor-deposited on the second electron transporting layer to form a 15-nm-thick third electron transporting layer.
LiF was vapor-deposited on the third 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.
A device arrangement of the organic EL device in Example 1 is roughly shown as follows.
ITO (130)/HT1:HA1 (10, 97%:3%)/HT1 (80)/HT2 (10)/PY1:BD1 (12.5, 96%/4%)/AN1 (12.5)/ET1 (10)/ET3 (15)/LiF (1)/Al (80)
The numerals in parentheses represent a film thickness (unit: nm).
The numerals (97%:3%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound HT1 and the compound HA1 in the hole injecting layer, and the numerals (96%:4%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (the compound PY1) and the compound BD1 in the emitting layer. Similar notations apply to the description below.
The organic EL device of Example 2 was manufactured in the same manner as in Example 1, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 1 with the compound listed in Table 1.
The organic EL device of Comparative Example 1 was manufactured in the same manner as in Example 1, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 1 with the compound listed in Table 1.
The organic EL device of Comparative Example 2 was manufactured in the same manner as in Example 1, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 1 with the compound listed in Table 1.
The organic EL devices manufactured in Examples 1 to 8 and Comparative Examples 1 to 8 were evaluated as follows. Evaluation results are shown in Tables 1 to 4.
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.
Table 1 shows relative values of lifetime LT90 of the organic EL devices of Example 1, Example 2, Comparative Example 1, and Comparative Example 2 to lifetime LT90 of the organic EL device of Comparative Example 1. The lifetimes as relative values were calculated according to an equation below.
Lifetime (relative value)=LTA/LTB
LTA: LT90 of the organic EL device for which the relative value is calculated
LTB: LT90 of the organic EL device of Comparative Example 1
Table 2 shows relative values of lifetime LT90 of the organic EL devices of Example 3, Example 4, Comparative Example 3, and Comparative Example 4 to lifetime LT90 of the organic EL device of Comparative Example 3. The lifetimes as relative values were calculated according to an equation below.
Lifetime (relative value)=LTA/LTB
LTA: LT90 of the organic EL device for which the relative value is calculated
LTB: LT90 of the organic EL device of Comparative Example 3
Table 3 shows relative values of lifetime LT90 of the organic EL devices of Example 5, Example 6, Comparative Example 5, and Comparative Example 6 to lifetime LT90 of the organic EL device of Comparative Example 5. The lifetimes as relative values were calculated according to an equation below.
Lifetime (relative value)=LTA/LTB
LTA: LT90 of the organic EL device for which the relative value is calculated
LTB: LT90 of the organic EL device of Comparative Example 5
Table 4 shows relative values of lifetime LT90 of the organic EL devices of Example 7, Example 8, Comparative Example 7, and Comparative Example 8 to lifetime LT90 of the organic EL device of Comparative Example 7. The lifetimes as relative values were calculated according to an equation below.
Lifetime (relative value)=LTA/LTB
LTA: LT90 of the organic EL device for which the relative value is calculated
LTB: LT90 of the organic EL device of Comparative Example 7
Each of the organic EL devices according to Examples 1 and 2 and Comparative Examples 1 and 2 includes the emitting layer, the first electron transporting layer directly adjacent to the emitting layer, and the second electron transporting layer directly adjacent to the first electron transporting layer. The emitting layer contains the first compound represented by Formula (1), and the first electron transporting layer contains the second compound represented by Formula (2). In Examples 1 and 2, the second electron transporting layer contains the third compound represented by Formula (3). In Comparative Examples 1 and 2, the second electron transporting layer contains a pyridine or imidazole derivative.
As shown in Table 1, the organic EL devices according to Examples 1 and 2 emitted light for a long lifetime by using the third compound represented by Formula (3) in the second electron transporting layer.
The organic EL devices were manufactured 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, a compound HT3 and the compound HA1 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. The ratios of the compound HT3 and the compound HA1 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 second hole transporting layer.
After the formation of the second hole transporting layer, a compound HT4 was vapor-deposited to form a 5-nm-thick first hole transporting layer.
A compound PY2 (host material) and a compound BD2 (dopant material (BD)) were co-deposited on the first hole transporting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 10-nm-thick first emitting layer.
A compound AN3 (host material) and the compound BD2 (dopant material) were co-deposited on the first emitting layer such that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 10-nm-thick second emitting layer.
A compound AN2 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 ET1 was vapor-deposited on the first electron transporting layer to form a 5-nm-thick second electron transporting layer (ET).
A compound ET4 and a compound Liq were co-deposited on the second electron transporting layer (ET) to form a 20-nm-thick third electron transporting layer (ET). The ratios of the compound ET4 and the compound Liq in the third electron transporting layer (ET) were both 50 mass %. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium.
Liq was vapor-deposited on the third 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.
A device arrangement of the organic EL device in Example 3 is roughly shown as follows.
ITO (130)/HT3:HA1 (10, 97%:3%)/HT3 (85)/HT4 (5)/PY2:BD2 (10, 98%:2%)/AN3:BD2 (10, 98%/2%)/AN2 (5)/ET1 (5)/ET4:Liq (20, 50%:50%)/Liq (1)/Al (80)
The numerals in parentheses represent a film thickness (unit: nm).
The numerals (97%:3%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound HT3 and the compound HA1 in the hole injecting layer, the numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (the compound PY2 or AN3) and the compound BD2 in the emitting layer, and the numerals (50%:50%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound ET4 and the compound Liq in the third electron transporting layer. Similar notations apply to the description below.
The organic EL device of Example 4 was manufactured in the same manner as in Example 3, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 3 with the compound listed in Table 2.
The organic EL devices of Comparative Examples 3 and 4 were manufactured in the same manner as in Example 3, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 3 with the compounds listed in Table 2.
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 HA1 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. The ratios of the compound HT3 and the compound HA1 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 second hole transporting layer.
After the formation of the second hole transporting layer, the compound HT4 was vapor-deposited to form a 5-nm-thick first hole transporting layer.
A compound PY3 (host material) and the compound BD2 (dopant material (BD)) were co-deposited on the first 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 AN3 (host material) and the compound BD2 (dopant material) were co-deposited on the first emitting layer so that a ratio of the compound BD2 accounted for 2 mass %, thereby forming a 15-nm-thick second emitting layer.
The compound AN3 was vapor-deposited on the second emitting layer to form a 2-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET1 was vapor-deposited on the first electron transporting layer to form a 5-nm-thick second electron transporting layer (ET).
The compound ET4 and the compound Liq were co-deposited on the second electron transporting layer (ET) to form a 23-nm-thick third electron transporting layer (ET). The ratios of the compound ET4 and the compound Liq in the third electron transporting layer (ET) were both 50 mass %. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium.
Liq was vapor-deposited on the third 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.
A device arrangement of the organic EL device in Example 5 is roughly shown as follows.
ITO (130)/HT3:HA1 (10, 97%:3%)/HT3 (85)/HT4 (5)/PY3:BD2 (5, 98%:2%)/AN3:BD2 (15, 98%:2%)/AN3 (2)/ET1 (5)/ET4:Liq (23, 50%:50%)/Liq (1)/Al (80) Numerals in parentheses represent a film thickness (unit: nm).
The numerals (97%:3%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound HT3 and the compound HA1 in the hole injecting layer, the numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (the compound PY3 or AN3) and the compound BD2 in the emitting layer, and the numerals (50%:50%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound ET4 and the compound Liq in the third electron transporting layer. Similar notations apply to the description below.
The organic EL device of Example 6 was manufactured in the same manner as in Example 5, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 5 with the compound listed in Table 3.
The organic EL devices of Comparative Examples 5 and 6 were manufactured in the same manner as in Example 5, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 5 with the compounds listed in Table 3.
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 HA1 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. The ratios of the compound HT3 and the compound HA1 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 second hole transporting layer.
After the formation of the second hole transporting layer, the compound HT4 was vapor-deposited to form a 5-nm-thick first hole transporting layer.
A compound PY4 (host material) and the compound BD2 (dopant material (BD)) were co-deposited on the first hole transporting layer so that a ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
The compound AN3 (host material) and the compound BD2 (dopant material) were co-deposited on the first emitting layer so that a ratio of the compound BD2 accounted for 2 mass %, thereby forming a 15-nm-thick second emitting layer.
The compound AN3 was vapor-deposited on the second emitting layer to form a 1-nm-thick first electron transporting layer (also referred to as a hole blocking layer (HBL)).
The compound ET1 was vapor-deposited on the first electron transporting layer to form a 5-nm-thick second electron transporting layer (ET).
The compound ET4 and the compound Liq were co-deposited on the second electron transporting layer (ET) to form a 24-nm-thick third electron transporting layer (ET). The ratios of the compound ET4 and the compound Liq in the third electron transporting layer (ET) were both 50 mass %. It should be noted that Liq is an abbreviation for (8-quinolinolato)lithium.
Liq was vapor-deposited on the third 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.
A device arrangement of the organic EL device in Example 7 is roughly shown as follows.
ITO (130)/HT3:HA1 (10, 97%:3%)/HT3 (85)/HT4 (5)/PY4:BD2 (5, 98%:2%)/AN3:BD2 (15, 98%:2%)/AN3 (1)/ET1 (5)/ET4:Liq (24, 50%:50%)/Liq (1)/Al (80)
The numerals (97%:3%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound HT3 and the compound HA1 in the hole injecting layer, the numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (the compound PY4 or AN3) and the compound BD2 in the emitting layer, and the numerals (50%:50%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound ET4 and the compound Liq in the third electron transporting layer. Similar notations apply to the description below.
The organic EL device of Example 8 was manufactured in the same manner as in Example 7, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 7 with the compound listed in Table 4.
The organic EL devices of Comparative Examples 7 and 8 were manufactured in the same manner as in Example 7, except that the second electron transporting layer was formed by replacing the compound used for forming the second electron transporting layer in Example 7 with the compounds listed in Table 4.
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. A toluene solution of the compound BD2 was prepared in the same manner as the compound BD1.
Using a fluorescence spectrometer (spectrophotofluorometer F-7000 manufactured by Hitachi High-Tech Science Corporation), the toluene solution of the compound BD1 or the toluene solution of the compound BD2 was excited at 390 nm, where a maximum fluorescence peak wavelength was measured.
The maximum fluorescence peak wavelength of the compound BD1 was 450 nm.
The maximum fluorescence peak wavelength of the compound BD2 was 455 nm.
1 . . . organic EL device, 1A . . . organic EL device, 2 . . . substrate, 3 . . . anode, 4 . . . cathode, 5 . . . emitting layer, 51 . . . first emitting layer, 52 . . . second emitting layer, 6 . . . hole injecting layer, 7 . . . hole transporting layer, 81 . . . first electron transporting layer, 82 . . . second electron transporting layer, 9 . . . electron injecting layer, 10 . . . organic layer.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2019-203447 | Nov 2019 | JP | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/JP2020/041600 | 11/6/2020 | WO |
