Patent Application
20240224791
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 voltage is applied to an 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 on a compound to be used for an organic EL device in order to enhance the performance of the organic EL device (see, for instance, Patent Literatures 1 to 5). The performance of the organic EL device is evaluable in terms of, for instance, luminance, emission wavelength, chromaticity, luminous efficiency, drive voltage, and lifetime.
An object of the invention is to provide an organic electroluminescence device excellent in performance. Another object of the invention is to provide an organic electroluminescence device excellent in at least one of a lifetime or luminous efficiency, and an electronic device including the organic electroluminescence device.
According to an aspect of the invention, there is provided an organic electroluminescence device, including:
In the formula (1):
In the first compound represented by the formula (1), R901, R902, R903, R904, R905, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
According to another aspect of the invention, there is provided an organic electroluminescence device in which the first compound represented by the formula (1) is a compound represented by a formula (1000) below and the first emitting layer contains, as the first host material, the first compound represented by the formula (1000).
In the formula (1000),
In the first compound represented by the formula (1000), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
According to still another aspect of the invention, there is provided an organic electroluminescence device, including:
In the formula (1):
In the formula (2):
In the first compound represented by the formula (1) and the second compound represented by the formula (2), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
According to a further aspect of the invention, there is provided an organic electroluminescence device in which the first compound represented by the formula (1) is a compound represented by a formula (1001) below and the first emitting layer contains, as the first host material, the first compound represented by the formula (1001).
In the formula (1001):
In the formula (111):
According to a still further aspect of the invention, there is provided an organic electroluminescence device, including:
In the formula (1001):
In the formula (111):
In the first compound represented by the formula (1001), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
According to a still further aspect of the invention, there is provided an organic electroluminescence device in which the first compound represented by the formula (1) is a compound represented by a formula (1002) below and the first emitting layer contains, as the first host material, the first compound represented by the formula (1002).
In the formula (1002):
In the first compound represented by the formula (1002), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
According to a still further aspect of the invention, there is provided an organic electroluminescence device, including:
In the formula (1002):
In the first compound represented by the formula (1002), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
According to a still further aspect of the invention, there is provided an organic electroluminescence device in which the first compound represented by the formula (1) is a compound represented by a formula (1003) or (1004) below and the first emitting layer contains, as the first host material, the first compound represented by the formula (1003) or (1004).
In the formula (1003):
In the formula (1004):
In the first compound represented by each of the formula (1003) and the formula (1004), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
According to a still further aspect of the invention, there is provided an organic electroluminescence device, including:
In the formula (1003):
In the formula (1004):
In the first compound represented by the formula (1003) or (1004), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
According to a still further aspect of the invention, there is provided an organic electroluminescence device in which the first compound represented by the formula (1) is a compound represented by a formula (1005) below and the first emitting layer contains, as the first host material, the first compound represented by the formula (1005).
In the formula (1005):
In the first compound represented by the formula (1005), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
According to a still further aspect of the invention, there is provided an organic electroluminescence device, including:
In the formula (1005):
In the first compound represented by the formula (1005), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
According to a still further aspect of the invention, there is provided an organic electroluminescence device in which the first compound represented by the formula (1) is a compound represented by a formula (1006) below and the first emitting layer contains, as the first host material, the first compound represented by the formula (1006).
In the formula (1006):
In the first compound represented by the formula (1006), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
According to a still further aspect of the invention, there is provided an organic electroluminescence device, including:
In the formula (1006):
In the first compound represented by the formula (1006), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
According to a still further aspect of the invention, there is provided an organic electroluminescence device in which the first compound represented by the formula (1) is a compound represented by a formula (1007) below and the first emitting layer contains, as the first host material, the first compound represented by the formula (1007).
In the formula (1007):
In the first compound represented by the formula (1007), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
According to a still further aspect of the invention, there is provided an electronic device including the organic electroluminescence device according to the aspect of the invention.
According to a still further aspect of the invention, an organic electroluminescence device excellent in performance can be provided. According to a still further aspect of the invention, an organic electroluminescence device excellent in at least one of a lifetime or luminous efficiency can be provided. According to a still further 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 is 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 does not include atoms of a substituent(s) of the substituted ZZ group. Herein, “YY” is larger than “XX,” “XX” representing an integer of 1 or more and “YY” representing an integer of 2 or more.
Herein, an unsubstituted ZZ group refers to an “unsubstituted ZZ group” in a “substituted or unsubstituted ZZ group,” and a substituted ZZ group refers to a “substituted ZZ group” in a “substituted or unsubstituted ZZ group.”
Herein, the term “unsubstituted” used in a “substituted or unsubstituted ZZ group” means that a hydrogen atom(s) in the ZZ group is not substituted with a substituent(s). The hydrogen atom(s) in the “unsubstituted ZZ group” is protium, deuterium, or tritium.
Herein, the term “substituted” used in a “substituted or unsubstituted ZZ group” means that at least one hydrogen atom in the ZZ group is substituted with a substituent. Similarly, the term “substituted” used in a “BB group substituted by AA group” means that at least one hydrogen atom in the BB group is substituted with the AA group.
Substituent mentioned herein 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). (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.
a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, 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.
an 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 group derived by substituting at least one hydrogen atom of a monovalent group derived from one of the cyclic structures represented by the formulae (TEMP-1) to (TEMP-15) with a substituent.
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 an “unsubstituted heterocyclic group” and a “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.
a 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.
a furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
Unsubstituted Heterocyclic Groups Including Sulfur Atom (Specific Example Group G2A3):
a 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 the formulae (TEMP-16) to (TEMP-33), XA and YA are each independently an oxygen atom, a sulfur atom, NH or CH2, with a proviso that at least one of XA or YA is an oxygen atom, a sulfur atom, or NH.
When at least one of XA or YA in the formulae (TEMP-16) to (TEMP-33) is NH or CH2, the monovalent heterocyclic groups derived from the cyclic structures represented by the formulae (TEMP-16) to (TEMP-33) include a monovalent group derived by removing one hydrogen atom from NH or CH2.
(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.
a phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
a phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and a 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 an “unsubstituted alkyl group” and a “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.
a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
a 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 an “unsubstituted alkenyl group” and a “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.
a vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
a 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.
an 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.
a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
a 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:
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:
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:
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:
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 “unsubstituted 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, and 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 occasionally 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. A 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 the formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
The dibenzofuranyl group and dibenzothiophenyl group mentioned herein are, unless otherwise specified herein, each specifically represented by one of formulae below.
In the formulae (TEMP-34) to (TEMP-41), * represents a bonding position.
Preferable examples of the substituted or unsubstituted alkyl group mentioned herein include, unless otherwise specified herein, a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t-butyl group.
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 the formulae (TEMP-42) to (TEMP-52), Q1 to Q10 are each independently a hydrogen atom or a substituent.
In the formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
In the formulae (TEMP-53) to (TEMP-62), Q1 to Q10 are each independently a hydrogen atom or a substituent.
In the formulae, Q9 and Q10 may be mutually bonded through a single bond to form a ring.
In the formulae, (TEMP-53) to (TEMP-62), * represents a bonding position.
In the formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.
In the formulae (TEMP-63) to (TEMP-68), * represents a bonding position.
The substituted or unsubstituted divalent heterocyclic group mentioned herein is, unless otherwise specified herein, preferably a group represented by any one of formulae (TEMP-69) to (TEMP-102) below.
In the formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.
In the 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 a formula (TEMP-103) below will be used as an example for the description.
For instance, when “at least one combination of adjacent two or more of R921 to R930 are mutually bonded to form a ring,” the 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 the formula (TEMP-103) is represented by a formula (TEMP-104) below.
The instance where the “combination of adjacent two or more” form a ring means not only an instance where the “two” adjacent components are bonded but also an instance where adjacent “three or more” are bonded. For instance, R921 and R922 are mutually bonded to form a ring QA and R922 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 the formula (TEMP-103) is represented by a formula (TEMP-105) below. In the formula (TEMP-105) below, the ring QA and the ring Qc share R922.
The formed “monocyclic ring” or “fused ring” may be, in terms of the formed ring in itself, a saturated ring or an unsaturated ring. When the “combination of adjacent two” form a “monocyclic ring” or a “fused ring,” the “monocyclic ring” or “fused ring” may be a saturated ring or an unsaturated ring. For instance, the ring QA and the ring QB formed in the formula (TEMP-104) are each independently a “monocyclic ring” or a “fused ring.” Further, the ring QA and the ring Qc formed in the formula (TEMP-105) are each a “fused ring.” The ring QA and the ring Qc in the formula (TEMP-105) are fused to form a fused ring. When the ring QA in the formula (TEMP-104) is a benzene ring, the ring QA is a monocyclic ring. When the ring QA in the formula (TEMP-104) is a naphthalene ring, the ring QA is a fused ring.
The “unsaturated ring” represents an aromatic hydrocarbon ring or an aromatic heterocycle. The “saturated ring” represents an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
Specific examples of the aromatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G1 with a hydrogen atom.
Specific examples of the aromatic heterocycle include a ring formed by terminating a bond of an aromatic heterocyclic group in the specific example of the specific example group G2 with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G6 with a hydrogen atom.
The phrase “to form a ring” herein means that a ring is formed only by a plurality of atoms of a basic skeleton, or by a combination of a plurality of atoms of the basic skeleton and one or more optional atoms. For instance, the ring QA formed by mutually bonding R921 and R922 shown in the formula (TEMP-104) is a ring formed by a carbon atom of the anthracene skeleton bonded 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 any other optional element than the 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 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 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, the substituent for the substituted or unsubstituted group (hereinafter occasionally referred to as an “optional substituent”), 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;
In an exemplary embodiment, the substituent for the substituted or unsubstituted group is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, the substituent for the substituted or unsubstituted group is a 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.
Specific examples of the above optional substituent are the same as the specific examples of the substituent described 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 an exemplary arrangement of the exemplary embodiment includes: an anode; a cathode; and an emitting layer provided between the anode and the cathode, in which the emitting layer includes a first emitting layer and a second emitting layer, and the first emitting layer contains, as a first host material, a first compound represented by a formula (1) below.
In an organic electroluminescence device according to an exemplary arrangement of the exemplary embodiment, the second emitting layer contains, as a second host material, a second compound represented by a formula (2) below.
In an organic electroluminescence device according to an exemplary arrangement of the exemplary embodiment, the first emitting layer contains, as the first host material, the first compound represented by the formula (1) below and the second emitting layer contains, as the second host material, the second compound represented by the formula (2) below.
Herein, the “host material” refers to, for instance, a material that accounts for “50 mass % or more of the layer”. That is, for instance, the first emitting layer contains 50 mass % or more of the first compound represented by the formula (1) below with respect to the total mass of the first emitting layer. For instance, the second emitting layer contains 50 mass % or more of the second compound represented by the formula (2) below with respect to the total mass of the second emitting layer. The host material is occasionally referred to as a matrix material.
The organic electroluminescence device according to an exemplary arrangement of the exemplary embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when being driven, more preferably emits light having a maximum peak wavelength in a range from 430 nm to 480 nm.
The maximum peak wavelength of the light emitted from the organic EL device when being driven is measured as follows. Voltage is applied to the organic EL device such that a current density becomes 10 mA/cm2, where spectral radiance spectrum is measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). A peak wavelength of an emission spectrum, a luminous intensity of which is the maximum in the obtained spectral radiance spectrum, is measured and defined as the maximum peak wavelength (unit:nm).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first emitting layer contains, as the first host material, the first compound represented by the formula (1) below. The first host material is a compound different from the second host material contained in the second emitting layer.
The first emitting layer preferably contains a first emitting compound. The first emitting compound and a second emitting compound may be mutually the same or different, preferably mutually the same. The emitting compound is occasionally referred to as a dopant material, guest material, emitter, or luminescent material.
The first emitting layer preferably contains the first emitting compound that emits light having a maximum peak wavelength of 500 nm or less. The first emitting compound is preferably a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less.
A method of measuring the maximum peak wavelength of the compound is as follows. A toluene solution of a measurement target compound at a concentration of 5 μmol/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 can be measured using a spectrophotometer (apparatus name: F-7000) produced by Hitachi High-Tech Science Corporation. It should be noted that the apparatus for measuring the emission spectrum is not limited to the apparatus 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 is occasionally referred to as a maximum fluorescence peak wavelength (FL-peak). From the emission spectrum measured, a full width at half maximum FWHM (unit: nm) of the maximum peak of the compound can be measured.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is a compound represented by the formula (1) below.
Herein, the “cyclic structure” includes not only a monocyclic compound but also a fused-ring compound, cross-linking compound, carbon ring compound, and heterocyclic compound.
In the formula (1):
In the first compound represented by the formula (1), R901, R902, R903, R904, R905, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound represented by the formula (1) is a compound represented by a formula (1000) below.
In an example of the formula (1000),
In the first compound represented by the formula (1000), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
In an example of the formula (1000),
In the first compound represented by the formula (1000), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is also preferably a compound represented by a formula (1A) below.
In the formula (1A), a cyclic structure A, a cyclic structure B, X1, R72A, and R73A each independently represent the same as the cyclic structure A, the cyclic structure B, X1, R72A, and R73A in the formula (1000).
In the formula (1A), preferably, R72A and R73A are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (1A), more preferably, R72A and R73A are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted dibenzoselenophenyl group, or a substituted or unsubstituted naphthobenzoselenophenyl group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the cyclic structure A and the cyclic structure B are preferably each independently a cyclic structure selected from the group consisting of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted phenalene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzofluorene ring, a substituted or unsubstituted dibenzofluorene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted perylene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted azanaphthalene ring, a substituted or unsubstituted azaanthracene ring, a substituted or unsubstituted azaphenanthrene ring, and a substituted or unsubstituted phenanthroline ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by a formula (100) below.
In the formula (100):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, at least one combination of a combination of adjacent two or more of R71 to R76 in X1 and a plurality of R101 and a combination of adjacent two or more of a plurality of R102 are preferably mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R71 to R76, R101 and R102 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably 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 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, more preferably, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, 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 the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (11) to (13) below.
In the formulae (11) to (12):
In the formula (13):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by a formula (12A), (12B), (12C), or (12D) below.
In the formula (12A):
In the formulae (12B), (12C), and (12D):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is also preferably a compound represented by a formula (12E) below.
In the formula (12E):
In the formula (12E), more preferably, the cyclic structure A1 and the cyclic structure B1 are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted 9,9′-spirobifluorene ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted benzocarbazole ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthobenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted naphthobenzothiophene ring, a substituted or unsubstituted dibenzoselenophene ring, or a substituted or unsubstituted naphthobenzoselenophene ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R11 to R18, R21 to R30, R31 to R38, R71 to R76, R71A to R78A and R103 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably 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 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, more preferably, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted dibenzoselenophenyl group, or a substituted or unsubstituted naphthobenzoselenophenyl group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is more preferable that:
In an example of the first compound, the groups specified to be “substituted or unsubstituted” are each preferably an unsubstituted group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound represented by the formula (1) is a compound represented by a formula (1001) below. A cyclic structure represented by the formula (1001) corresponds to the cyclic structure B in the formula (1), and a cyclic structure A in a formula (111) below corresponds to the cyclic structure A in the formula (1).
In the formula (1001):
In the formula (111):
In the first compound represented by the formula (1001), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the organic EL device according to an exemplary arrangement of the above exemplary embodiment, the structure represented by the formula (111) is preferably a structure represented by a formula (11A) below.
In the formula (11A):
In the formula (11A), preferably, no combination of adjacent two or more of R1 to R4 are mutually bonded.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (12) to (14) below.
In the formulae (12) to (14), R101 to R110 and X1 each independently represent the same as R101 to R110 and X1 in the formula (1001), and R1 to R4 each independently represent the same as R1 to R4 in the formula (11A).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is also preferably a compound represented by a formula (12-1), (13-1), or (14-1) below.
In the formula (12-1), (13-1), or (14-1), R1 to R4, R101 to R106, R108 and X1 each independently represent the same as R1 to R4, R101 to R106, R108 and X1 in the formula (1), and R1 to R4 each independently represent the same as R1 to R4 in the formula (11A).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R101 to R110, R1 to R4, and R71 to R76 forming neither the monocyclic ring nor the fused ring are preferably 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 cycloalkyl group having 3 to 50 ring carbon atoms, 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 -(L900)nx-Ar900.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, more preferably, R101 to R110 and R1 to R4 forming neither the monocyclic ring nor the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a group represented by -(L900)nx-Ar900.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R71 to R76 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the group represented by -(L900)nx-Ar900 is preferably a group represented by one of formulae (12A) to (14A) below.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, more preferably, the group represented by -(L900)nx-Ar900 is a group represented by one of the formulae (12A) to (14A) below and one of R1 to R4 is a group represented by one of the formulae (12A) to (14A) below.
In the formulae (12A) to (14A):
In the formulae (12A) to (14A):
In the formulae (12A) to (14A), it is preferable that:
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, nx in the group represented by -(L900)nx-Ar900 is preferably 0, 1 or 2.
L900 in the group represented by -(L900)nx-Ar900 is preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothienylene group.
Ar900 in the group represented by -(L900)nx-Ar900 is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, Ra, R1 to R4, R71 to R76, R101 to R110 and R1001 to R1010 forming neither the monocyclic ring nor the fused ring are preferably 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 cycloalkyl group having 3 to 50 ring carbon atoms, 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 -(L900)nx-Ar900, more preferably, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a group represented by -(L900)nx-Ar900.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, X1 is preferably an oxygen atom, a sulfur atom, NR71, or C(R72)(R73).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when X1 is C(R72)(R73), a combination of R72 and R73 are preferably mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when X1 is C(R72)(R73), a combination of R72 and R73 are also preferably not mutually bonded.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when X1 is NR71 or C(R72)(R73), R71 to R73 are preferably 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, more preferably, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, 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 example of the first compound, the groups specified to be “substituted or unsubstituted” are each preferably an unsubstituted group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound represented by the formula (1) is a compound represented by a formula (1002) below. In the formula (1002), a cyclic structure having R1 to R4 corresponds to the cyclic structure B in the formula (1), and cyclic structures respectively having A10, B10 and C10 correspond to the cyclic structure A in the formula (1).
In the formula (1002):
In the formulae (111P) to (116P) and (111A) to (112A):
In the first compound represented by the formula (1002), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
In the formula (1002), R71B, R72B, R73B, R74B, R75B, R76B, R77B, and R78B each independently represent the same as R71A, R72A, R73A, R74A, R75A, R76A, R77A, and R78A in the formula (1).
In an example of the formula (1002),
In the first compound represented by the formula (1002), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (11P) to (16P) below.
In the formulae (11P) to (16P):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (11AP) to (16AP) below.
In the formulae (11 AP) to (16AP):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is also preferably a compound represented by one of formulae (17A) to (22A) below.
In the formulae (17A) to (22A):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, at least one combination of a combination of adjacent two or more of R1 to R4, and a combination of adjacent two or more of R1, R4, R71 to R78, R71A to R78A, R71B to R78B and a plurality of Ra are preferably mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, also preferably, none of a combination of adjacent two or more of R1 to R4 and a combination of adjacent two or more of R1, R4, R71 to R76, R71A to R78A, R71B to R78B and a plurality of Ra are mutually bonded.
In the organic EL device according to an exemplary arrangement of the above exemplary embodiment, it is preferable that:
In the organic EL device according to an exemplary arrangement of the above exemplary embodiment, it is preferable that R1 to R4, R71 to R78, R71A to R78A, R71B to R78B, and Ra forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring 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 cycloalkyl group having 3 to 50 ring carbon atoms, 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 -(L900)nx-Ar900.
In the formulae (11 AP) to (16AP) and (17A) to (22A), it is preferable that:
In the formulae (11AP) to (16AP) and (17A) to (22A), it is preferable that R1 to R4, R71 to R78, R71A to R78A, and Ra forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring 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 cycloalkyl group having 3 to 50 ring carbon atoms, 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 -(L900)nx-Ar900.
In the organic EL device according to an exemplary arrangement of the above exemplary embodiment, R1 to R4, R71 to R78, R71A to R78A, R71B to R78B, and Ra forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a group represented by -(L900)nx-Ar900.
In the organic EL device according to an exemplary arrangement of the above exemplary embodiment, it is more preferable that R1 to R4, R71 to R78, R71A to R78A, R71B to R78B, and Ra forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benz(a)anthracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, or a group represented by -(L900)nx-Ar900.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, nx in the group represented by -(L900)nx-Ar900 is preferably 0, 1 or 2.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, L900 in the group represented by -(L900)nx-Ar900 is preferably 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, more preferably a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, Ar900 in the group represented by -(L900)nx-Ar900 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, more preferably, 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 example of the first compound, the groups specified to be “substituted or unsubstituted” are each preferably an unsubstituted group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound represented by the formula (1) is a compound represented by a formula (1003) or (1004) below.
A cyclic structure A in the formula (1003) corresponds to the cyclic structure A in the formula (1), and a cyclic structure B in the formula (1003) corresponds to the cyclic structure B in the formula (1).
A cyclic structure Ax in the formula (1004) corresponds to the cyclic structure A in the formula (1), and a cyclic structure B in the formula (1004) corresponds to the cyclic structure B in the formula (1).
In the formula (1003):
In the formula (1004):
In the formula (1003), R102X represents the same as R71A in the formula (1). In the first compound represented by each of the formula (1003) and the formula (1004), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
In the first compound represented by each of the formula (1003) and the formula (1004), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by a formula (1-1) below.
In the formula (1-1):
In the formula (1-1), preferably, no combination of adjacent two or more of R11 to R26 are mutually bonded.
In the formula (1-1), R11 to R26 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably 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 cycloalkyl group having 3 to 50 ring carbon atoms, 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 -(L900)nx-Ar900.
In the formula (1-1), R11 to R26 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a group represented by —Si(R901)(R902)(R903), or a group represented by -(L900)nx-Ar900.
The group represented by -(L900)nx-Ar900 is preferably a group represented by a formula (1-2) or (1-3) below, more preferably a group represented by the formula (1-2).
In the formula (1-2):
In the formula (1-3):
In the formulae (1-2) and (1-3), R11A to R18A, R23A to R26A, R31, R31A to R41A and R71A to R73A forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably 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 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; more preferably, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, 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 the organic EL device according to an exemplary arrangement of the exemplary embodiment, nx in the group represented by -(L900)nx-Ar900 is preferably 0, 1 or 2.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, L900 in the group represented by -(L900)nx-Ar900 is preferably a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothienylene group, or a group represented by —Si(R901A)(R902B)—.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when L900 is a group represented by —Si(R901A)(R902B)—, R901A and R902B are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, 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 the organic EL device according to an exemplary arrangement of the exemplary embodiment, Ar900 in the group represented by -(L900)nx-Ar900 is also preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by a formula (100-1) below.
The compound represented by the formula (100-1) is usable also as an emitting compound. In this arrangement, the compound represented by the formula (100-1) is usable, for instance, as the second emitting compound and a third emitting compound described later.
In the formula (100-1):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by a formula (100-2) below.
In the formula (100-2):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R102X and R103X forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R101 to R111 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably 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 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 an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by a formula (100-21), (100-21A), or (100-21B) below.
In the formula (100-21):
In an exemplary embodiment, R101 to R111 and R542 to R551 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, R101 to R111 and R542 to R551 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, R101 to R111 and R542 to R551 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, R101 to R111 and R542 to R551 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
In an exemplary embodiment, the compound represented by the formula (100-21) is a compound represented by a formula (100-21A) below.
In the formula (100-21A), R102, R106, R109, R544 and R549 each independently represent the same as R102, R106, R109, R544 and R549 in the formula (100-21).
In the formula (100-21B), R102, R105, R110, R543 and R550 each independently represent the same as R102, R105, R110, R543 and R550 in the formula (100-21).
In an example of the first compound, the groups specified to be “substituted or unsubstituted” are each preferably an unsubstituted group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound represented by the formula (1) is a compound represented by a formula (1005) below.
A cyclic structure having R17 to R20 in the formula (1005) corresponds to the cyclic structure A in the formula (1), and a cyclic structure having R11 to R16 in the formula (1005) corresponds to the cyclic structure B in the formula (1).
In the formula (1005):
In the first compound represented by the formula (1005), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
In the first compound represented by the formula (1005), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, preferably, none of a combination of adjacent two or more of R11 to R16 and a combination of adjacent two or more of R17 to R20 are mutually bonded.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, also preferably, at least one combination of a combination of adjacent two or more of R11 to R16, and a combination of adjacent two or more of R17 to R20 are mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (11Q) to (14Q) below.
In the formulae (11 Q) to (14Q):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is also preferably a compound represented by one of formulae (15) to (20) below.
In the formulae (15) to (20):
In the formulae (11Q) to (14Q) and (15) to (20), R11 to R20 are preferably 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 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; more preferably, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, 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 the organic EL device according to an exemplary arrangement of the exemplary embodiment, nx in the group represented by -(L900)nx-Ar900 is preferably 0, 1 or 2.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, L900 in the group represented by -(L900)nx-Ar900 is preferably each independently a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms; more preferably, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothienylene group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, Ar900 in the group represented by -(L900)nx-Ar900 is preferably each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a group represented by a formula (1A) below; more preferably, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benz(a)anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a group represented by a formula (1A) below.
In the formula (1A):
Assuming that the first compound is a compound represented by one of the formulae (11Q) to (14Q) and (15) to (20), one of carbon atoms bonded to R11A to R20A and R72 to R73, a nitrogen atom bonded to R71, a silicon atom bonded to R74 to R75, and a phosphorus atom bonded to R76 is bonded, when nx is 0, to *1 in the formulae (11Q) to (14Q) and (15) to (20), and is bonded, when nx is 1, 2, or 3, to L900.
In the organic EL device according to an exemplary arrangement of the above exemplary embodiment, R11 to R20 and R71 to R76 are preferably 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 cycloalkyl group having 3 to 50 ring carbon atoms, 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 -(L900)nx-Ar900.
In the organic EL device according to an exemplary arrangement of the above exemplary embodiment, it is preferable that:
In an example of the first compound, the groups specified to be “substituted or unsubstituted” are each preferably an unsubstituted group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound represented by the formula (1) is a compound represented by a formula (1006) below. A cyclic structure A in the formula (1006) corresponds to the cyclic structure A in the formula (1), and a cyclic structure B in the formula (1006) corresponds to the cyclic structure B in the formula (1).
In the formula (1006):
In the first compound represented by the formula (1006), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1006).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that one of Z1 and Z2 is a carbon atom, and it is more preferable that Z1 and Z2 are each a carbon atom.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the cyclic structure A and the cyclic structure B are preferably each independently a cyclic structure selected from the group consisting of a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted phenalene ring, a substituted or unsubstituted pyrene ring, a substituted or unsubstituted chrysene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzofluorene ring, a substituted or unsubstituted dibenzofluorene ring, a substituted or unsubstituted fluoranthene ring, a substituted or unsubstituted perylene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted azanaphthalene ring, a substituted or unsubstituted azaanthracene ring, a substituted or unsubstituted azaphenanthrene ring, and a substituted or unsubstituted phenanthroline ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by a formula (10) below.
In the formula (10):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, at least one combination of a combination of adjacent two or more of R1 to R4, and a combination of adjacent two or more of R5 to R8 are preferably mutually bonded to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 18 ring atoms.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, at least one combination of two or more of a combination of R1 and R2, a combination of R3 and R4, a combination of R5 and R6, and R7 and R8 are more preferably mutually bonded to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 18 ring atoms.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R1 to R8 and R71 to R76 forming neither the monocyclic ring nor the fused ring are preferably 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 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 an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (11R) to (16R) below.
In the formula (11R):
In the formula (11R), at least one combination of adjacent two or more of R1 to R2, R7 to Ra, R11 to R14 and R21 to R24 preferably form neither a substituted or unsubstituted monocyclic ring nor a substituted or unsubstituted fused ring.
In the formula (12R), at least one combination of adjacent two or more of R1 to R2, R5 to R6, R11 to R14 and R31 to R34 preferably form neither a substituted or unsubstituted monocyclic ring nor a substituted or unsubstituted fused ring.
In the formula (13R), at least one combination of adjacent two or more of R1 to R2, R11 to R14, R21 to R24 and R31 to R34 preferably form neither a substituted or unsubstituted monocyclic ring nor a substituted or unsubstituted fused ring.
In the formula (14R), at least one combination of adjacent two or more of R3 to R4, R21 to R24, R31 to R34 and R41 to R44 preferably form neither a substituted or unsubstituted monocyclic ring nor a substituted or unsubstituted fused ring.
In the formula (15R), at least one combination of adjacent two or more of R1 to R4, R21 to R24 and R31 to R34 preferably form neither a substituted or unsubstituted monocyclic ring nor a substituted or unsubstituted fused ring.
In the formula (16R), at least one combination of adjacent two or more of R11 to R14, R21 to R24, R31 to R34 and R41 to R44 preferably form neither a substituted or unsubstituted monocyclic ring nor a substituted or unsubstituted fused ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that R1 to Ra, R11 to R14, R21 to R24, R31 to R34, R41 to R44 and R71 to R76 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 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; and it is more preferable that R1 to Ra, R11 to R14, R21 to R24, R31 to R34, R41 to R44 and R71 to R76 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, 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 the organic EL device according to an exemplary arrangement of the exemplary embodiment, R1 to Ra, R11 to R14, R21 to R24, R31 to R34 and R41 to R44 are each preferably a hydrogen atom.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that:
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, X1 is preferably C(R72)(R73).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R71 to R76 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, 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 example of the first compound, the groups specified to be “substituted or unsubstituted” are each preferably an unsubstituted group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound represented by the formula (1) is a compound represented by a formula (1007) below.
A cyclic structure having R105 to R108 in the formula (1007) corresponds to the cyclic structure A in the formula (1), and a cyclic structure having R101 to R104 in the formula (1007) corresponds to the cyclic structure B in the formula (1).
In the formula (1007):
In the first compound represented by the formula (1007), R901, R902, R903, R904, R905, R801 and R802 each independently represent the same as R901, R902, R903, R904, R905, R801 and R802 in the formula (1).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that at least one combination of adjacent two or more of R101 to R110 are mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (101) to (105) below.
In the formulae (101) to (105):
The compound represented by the formula (1007) is preferably a compound in which the total number of rings of a basic skeleton is 5 or less. The compound in which the total number of rings of the basic skeleton is 5 or less is explained with examples.
For instance, in the compound represented by the formula (1007), when no combination of adjacent two or more of R101 to R110 are mutually bonded, “the total number of rings of the basic skeleton” is three.
In the compound represented by the formula (101), no combination of adjacent two or more of R103 to R110 are mutually bonded. Thus, in the compound represented by the formula (101), when the cyclic structure A100 is a substituted or unsubstituted benzene ring, “the total number of rings of the basic skeleton” is four. Further, when the cyclic structure A100 is a substituted or unsubstituted naphthalene ring, “the total number of rings of the basic skeleton” is five.
In the compound represented by the formula (104), no combination of adjacent two or more of R101 to R103 and R108 to R110 are mutually bonded. Thus, in the compound represented by the formula (104), when the combination of R72B and R73B are not mutually bonded, the combination of R74B and R75B are not mutually bonded, and the cyclic structure D100 is a substituted or unsubstituted benzene ring, “the total number of rings of the basic skeleton” is five.
In the compound represented by the formula (1007), the number of the ring atoms of a basic skeleton of a cyclic structure represented by the formula (1007) is preferably in a range from 18 to 22.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound is preferably a compound represented by one of formulae (101A) to (105A) below.
In the formulae (101A) to (105A), R101 to R114 each independently represent the same as R101 to R110 in the formula (1007), no combination of adjacent two or more of R101 to R114 being mutually bonded, and
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, no combination of adjacent two or more of R101 to R110 are preferably mutually bonded.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R101 to R114 forming neither the substituted or unsubstituted monocyclic ring nor the substituted or unsubstituted fused ring are preferably 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 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 an exemplary arrangement of the exemplary embodiment, it is preferable that X100 is an oxygen atom, a sulfur atom, NR71B, or C(R72B)(R73B); and R71B, R72B, and R73B are each independently 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 substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first compound can be produced by a known method. The first compound can also be produced 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. However, the invention is not limited to the specific examples of the first compound.
In addition to the above examples, the following examples are also included in the specific examples of the first compound.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when the first emitting layer contains the first host material and the first emitting compound, a singlet energy of the first host material S1(H1) and a singlet energy of the first emitting compound S1(D1) preferably satisfy a relationship of a numerical formula (Numerical Formula 1) below.
S
1(H1)>S1(D1) (Numerical Formula 1)
An 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 (300K). A tangent is drawn to the fall of the absorption spectrum close to the long-wavelength region, 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.
Conversion Equation(F2): S1[eV]=12390.85/λedge
Any apparatus for measuring the absorption spectrum is usable. For instance, a spectrophotometer (U3310 produced by Hitachi, Ltd.) is usable.
The tangent to the fall of the absorption spectrum close to the long-wavelength region is drawn as follows. While moving on a curve of the absorption spectrum from the local maximum value closest to the long-wavelength region, among the local maximum values of the absorption spectrum, in a long-wavelength direction, a tangent at each point on the curve is checked. An inclination of the tangent is decreased and increased in a repeated manner as the curve falls (i.e., a value of the ordinate axis is decreased). A tangent drawn at a point where the inclination of the curve is the local minimum closest to the long-wavelength region (except when absorbance is 0.1 or less) is defined as the tangent to the fall of the absorption spectrum close to the long-wavelength region.
The local maximum absorbance of 0.2 or less is not counted as the above-mentioned local maximum absorbance closest to the long-wavelength region.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when the first emitting layer and the second emitting layer are layered in this order from a side close to the anode, it is preferable that an electron mobility of the first host material μE1(H1), a hole mobility of the first host material μH1(H1), an electron mobility of the second host material μE2(H2), and a hole mobility of the second host material μH2(H2) satisfy a relationship of a numerical formula (Numerical Formula 15) below.
(μE2(H2)/μH2(H2))>(μE1(H1)/μH1(H1)) (Numerical Formula 15)
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when the first emitting layer and the second emitting layer are layered in this order from the side close to the anode, it is preferable that the electron mobility of the first host material μE1(H1) and the electron mobility of the second host material μE2(H2) satisfy a relationship of a numerical formula (Numerical Formula 16) below.
When the first host material and the second host material satisfy the relationship of the numerical formula (Numerical Formula 16), a recombination ability between holes and electrons in the first emitting layer is improved.
μE2(H2)>μE1(H1) (Numerical Formula 16)
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when the first emitting layer and the second emitting layer are layered in this order from the side close to the anode, it is also preferable that the hole mobility of the first host material μH1(H1) and the hole mobility of the second host material μH2(H2) satisfy a relationship of a numerical formula (Numerical Formula 17) below.
μH1(H1)>μH2(H2) (Numerical Formula 17)
The electron mobility can be measured according to an impedance measurement using a mobility evaluation device produced by the following steps. The mobility evaluation device is, for instance, produced by the following steps.
A compound Target, which is to be measured for an electron mobility, is vapor-deposited on a glass substrate having an aluminum electrode (anode) so as to cover the aluminum electrode, thereby forming a measurement target layer. A compound ET-A below is vapor-deposited on this measurement target layer to form an electron transporting layer. LiF is vapor-deposited on this formed electron transporting layer to form an electron injecting layer. Metal aluminum (Al) is vapor-deposited on this formed electron injecting layer to form a metal cathode.
An arrangement of the mobility evaluation device above is roughly shown as follows.
Numerals in parentheses represent a film thickness (nm).
The mobility evaluation device for the electron mobility is set in an impedance measurement apparatus to perform an impedance measurement. In the impedance measurement, a measurement frequency is swept from 1 Hz to 1 MHz. At this time, an alternating current amplitude of 0.1 V and a direct current voltage V are applied to the device. A modulus M is calculated from a measured impedance Z using a relationship of a calculation formula (C1) below.
Calculation formula(C1): M=jωZ
In the calculation formula (C1), j is an imaginary unit whose square is −1 and ω is an angular frequency [rad/s].
In a bode plot in which an imaginary part of the modulus M is represented by an ordinate axis and the frequency [Hz] is represented by an abscissa axis, an electrical time constant τ of the mobility evaluation device is obtained from a frequency fmax showing a peak using a calculation formula (C2) below.
Calculation formula(C2): τ=1/(2ττfmax)
ττ in the calculation formula (C2) is a symbol representing a circumference ratio.
An electron mobility μe is calculated from a relationship of a calculation formula (C3-1) below using τ.
Calculation formula(C3-1): μe=d2/(Vτ)
d in the calculation formula (C3-1) is a total film thickness of organic thin film(s) forming the device. In a case of the arrangement of the mobility evaluation device for the electron mobility, d=210 [nm] is satisfied.
The hole mobility can be measured according to an impedance measurement using a mobility evaluation device produced by the following steps. The mobility evaluation device is, for instance, produced by the following steps.
A compound HA-2 below is vapor-deposited on a glass substrate having an ITO transparent electrode (anode) so as to cover the transparent electrode, thereby forming a hole injecting layer. A compound HT-A below is vapor-deposited on this formed hole injecting layer to form a hole transporting layer. Subsequently, a compound Target, which is to be measured for a hole mobility, is vapor-deposited to form a measurement target layer. Metal aluminum (Al) is vapor-deposited on this measurement target layer to form a metal cathode.
An arrangement of the mobility evaluation device above is roughly shown as follows.
ITO(130)/HA-2(5)/HT-A(10)/Target(200)/Al(80)
Numerals in parentheses represent a film thickness (nm).
The mobility evaluation device for the hole mobility is set in an impedance measurement apparatus to perform an impedance measurement. In the impedance measurement, a measurement frequency is swept from 1 Hz to 1 MHz. At this time, an alternating current amplitude of 0.1 V and a direct current voltage V are applied to the device. A modulus M is calculated from a measured impedance Z using the relationship of the calculation formula (C1).
In a bode plot in which an imaginary part of the modulus M is represented by an ordinate axis and the frequency [Hz] is represented by an abscissa axis, an electrical time constant T of the mobility evaluation device is obtained from a frequency fmax showing a peak using the calculation formula (C2).
A hole mobility μh is calculated from a relationship of a calculation formula (C3-2) below using T obtained from the calculation formula (C2).
Calculation formula(C3-2): ρh=d2/(VT)
d in the calculation formula (C3-2) is a total film thickness of organic thin film(s) forming the device. In a case of the arrangement of the mobility evaluation device for the hole mobility, d=215 [nm] is satisfied.
The electron mobility and the hole mobility herein are each a value obtained in a case where a square root of an electric field intensity meets E1/2=500 [V1/2/cm1/2]. The square root of the electric field intensity, E1/2, can be calculated from a relationship of a calculation formula (C4) below.
Calculation formula(C4): E1/2=V1/2/d1/2
For the impedance measurement, a 1260 type by Solartron Analytical is used as the impedance measurement apparatus, and for a higher accuracy, a 1296 type dielectric constant measurement interface by Solartron Analytical can be used together therewith.
The first emitting layer preferably does not contain a phosphorescent material (phosphorescent dopant material).
The first 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 first emitting layer also preferably does not contain a metal complex.
The film thickness of the first emitting layer is preferably 3 nm or more, more preferably 5 nm or more. When the film thickness of the first emitting layer is 3 nm or more, the film thickness is sufficiently large to cause recombination of holes and electrons in the first emitting layer.
The film thickness of the first emitting layer is preferably 15 nm or less, more preferably 10 nm or less.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the film thickness of the first emitting layer is more preferably in a range from 3 nm to 15 nm.
When the first emitting layer contains the first host material as the first compound and the first emitting compound, the content of each of the first host material and the first emitting compound in the first emitting layer preferably falls, for instance, within a range below.
The content of the first host material is preferably in a range from 80 mass % to 99 mass %, more preferably in a range from 90 mass % to 99 mass %, and still more preferably in a range from 95 mass % to 99 mass %.
The content of the first emitting compound is preferably in a range from 1 mass % to 10 mass %, more preferably in a range from 1 mass % to 7 mass %, and still more preferably in a range from 1 mass % to 5 mass %.
The upper limit of the total of the contents of the first host material and the first emitting compound in the first emitting layer is 100 mass %.
It should be noted that the first emitting layer of the exemplary embodiment may further contain any other material(s) than the first host material and the first emitting compound.
The first emitting layer may contain a single type of the first host material or may contain two or more types of the first host material. The first emitting layer may contain a single type of the first emitting compound or may contain two or more types of the first emitting compound.
The second emitting layer contains, as the second host material, the second compound represented by a formula (2) below. The second host material is a compound different from the first host material contained in the first emitting layer.
The second emitting layer preferably contains the second emitting compound. The second emitting compound and the first emitting compound may be mutually the same or different, preferably mutually the same.
The second emitting layer preferably contains the second emitting compound that emits light having a maximum peak wavelength of 500 nm or less. The second emitting compound is preferably a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less.
A measurement method of the maximum peak wavelength of the compound is as follows.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the second compound is a compound represented by the formula (2) below.
In the formula (2):
In the second compound represented by the formula (2), R901, R902, R903, R904, R905, R906, R907, R801 and R802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that:
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that:
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, Ar201 and Ar202 are preferably each independently 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 according to an exemplary arrangement of the exemplary embodiment, the second compound represented by the formula (2) is preferably a compound represented by a formula (201), a formula (202), a formula (203), a formula (204), a formula (205), a formula (206), a formula (207), a formula (208), or a formula (209) below.
In the formulae (201) to (209):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that:
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that:
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that Ar201 and Ar202 are each independently 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.
The second compound represented by the formula (2) is also preferably a compound represented by a formula (221), a formula (222), a formula (223), a formula (224), a formula (225), a formula (226), a formula (227), a formula (228), or a formula (229) below.
In the formulae (221), (222), (223), (224), (225), (226), (227), (228) and (229):
The second compound represented by the formula (2) is also preferably a compound represented by a formula (241), a formula (242), a formula (243), a formula (244), a formula (245), a formula (246), a formula (247), a formula (248), or a formula (249) below.
In the formulae (241), (242), (243), (244), (245), (246), (247), (248) and (249):
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, R201 to R208 that are substituents of an anthracene skeleton in the second compound represented by the formula (2) are preferably hydrogen atoms in terms of preventing inhibition of intermolecular interaction and inhibiting a decrease in electron mobility. However, R201 to R208 may be 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.
It should be noted that substituents, namely, a haloalkyl group, alkenyl group, alkynyl group, group represented by —Si(R901)(R902)(R903), group represented by —O—(R904), group represented by —S—(R905), group represented by —N(R906)(R907), aralkyl group, group represented by —C(═O)R801, group represented by —COOR802, halogen atom, cyano group, and nitro group are likely to be bulky, and an alkyl group and cycloalkyl group are likely to be further bulky.
In the second compound represented by the formula (2), R201 to R208, which are the substituents on the anthracene skeleton, are each preferably not a bulky substituent and preferably not an alkyl group and cycloalkyl group. More preferably, R201 to R208 are each not an alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, group represented by —Si(R901)(R902)(R903), group represented by —O—(R904), group represented by —S—(R905), group represented by —N(R906)(R907), aralkyl group, group represented by —C(═O)R801, group represented by —COOR802, halogen atom, cyano group, and nitro group.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is also preferable that R201 to R208 in the second compound represented by the 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 an exemplary arrangement of the exemplary embodiment, R201 to R208 in the second compound represented by the formula (2) are each preferably a hydrogen atom.
In the second compound, examples of the substituent for the “substituted or unsubstituted” group on R201 to R208 also preferably do not include the above-described substituent that is likely to be bulky, especially a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group. When examples of the substituent for the “substituted or unsubstituted” group on R201 to R208 do not include a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group, the inhibition of intermolecular interaction to be caused by the presence of a bulky substituent such as an alkyl group and a cycloalkyl group can be prevented, thereby preventing a decrease in the electron mobility. Moreover, when the second compound described above is used in the second emitting layer, a decrease in a recombination ability between holes and electrons in the first emitting layer and a decrease in the luminous efficiency can be inhibited.
Further preferably, R201 to R208 that are the substituents on the anthracene skeleton are not bulky substituents and R201 to R208 as the substituents are unsubstituted. Assuming that R201 to R208 that are the substituents on the anthracene skeleton are not bulky substituents and substituents are bonded to R201 to R208 that are not the bulky substituents, the substituents bonded to R201 to R208 are preferably not bulky substituents; and the substituents bonded to R201 to R208 serving as the substituents are preferably not an alkyl group and cycloalkyl group, more preferably not an alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, group represented by —Si(R901)(R902)(R903), group represented by —O—(R904), group represented by —S—(R905), group represented by —N(R906)(R907), aralkyl group, group represented by —C(═O)R801, group represented by —COOR802, halogen atom, cyano group, and nitro group.
In the second compound, the groups specified to be “substituted or unsubstituted” are each preferably an unsubstituted group.
The second compound can be produced by a known method. The second compound can also be produced 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. However, the invention is not limited to the specific examples of the second compound.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, when the second emitting layer contains the second host material and the second emitting compound, a singlet energy of the second host material S1(H2) and a singlet energy of the second emitting compound S1(D2) preferably satisfy a relationship of a numerical formula (Numerical Formula 2) below.
S
1(H2)>S1(D2) (Numerical Formula 2)
The second emitting layer preferably does not contain a phosphorescent material (phosphorescent dopant material).
The second 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 second emitting layer also preferably does not contain a metal complex.
The film thickness of the first emitting layer is preferably 5 nm or more, more preferably 15 nm or more.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the film thickness of the second emitting layer is preferably 20 nm or less.
When the second emitting layer contains the second host material as the second compound and the second emitting compound, the content of each of the second host material and the second emitting compound in the second emitting layer preferably falls, for instance, within a range below.
The content of the second host material is preferably in a range from 80 mass % to 99 mass %, more preferably in a range from 90 mass % to 99 mass %, and still more preferably in a range from 95 mass % to 99 mass %.
The content of the second emitting compound is preferably in a range from 1 mass % to 10 mass %, more preferably in a range from 1 mass % to 7 mass %, and still more preferably in a range from 1 mass % to 5 mass %.
The upper limit of the total of the contents of the second host material and the second emitting compound in the second emitting layer is 100 mass %.
The second emitting layer of the exemplary embodiment may further contain any other material than the second host material and the second emitting compound.
The second emitting layer may contain a single type of the second host material or may contain two or more types of the second host material. The second emitting layer may contain a single type of the second emitting compound or may contain two or more types of the second emitting compound.
In addition to the first emitting layer and the second emitting layer, the organic EL device according to an exemplary arrangement of the exemplary embodiment may include one or more organic layers. Examples of the organic layer include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an emitting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, and an electron blocking layer.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, only the first emitting layer and the second emitting layer may be included as the organic layers. Alternatively, 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 may be further included as the organic layer.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the hole transporting layer is preferably provided between the emitting layers and the anode.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the electron transporting layer is preferably provided between the emitting layers and the cathode.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is preferable that the first emitting layer is preferably provided between the anode and the cathode and the second emitting layer is provided between the first emitting layer and the cathode.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the anode, the first emitting layer, the second emitting layer, and the cathode may be provided in this order. Alternatively, the anode, the second emitting layer, the first emitting layer, and the cathode may be provided in this order.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, it is also preferable that the first emitting layer is provided between the anode and the cathode and the second emitting layer is provided between the first emitting layer and the anode.
The organic EL device 1 includes a light-transmissive substrate 2, an anode 3, a cathode 4, and organic layers 10 provided between the anode 3 and the cathode 4. The organic layers 10 include the hole injecting layer 6, the hole transporting layer 7, the first emitting layer 51, the second emitting layer 52, the electron transporting layer 8, and the electron injecting layer 9 that are layered on the anode 3 in this order.
An organic EL device 1A includes the light-transmissive substrate 2, the anode 3, the cathode 4, and organic layers 10A provided between the anode 3 and the cathode 4. The organic layers 10A include the hole injecting layer 6, the hole transporting layer 7, the second emitting layer 52, the first emitting layer 51, the electron transporting layer 8, and the electron injecting layer 9 that are layered on the anode 3 in this order.
The organic EL device according to an exemplary arrangement of the exemplary embodiment may further include a third emitting layer.
The third emitting layer contains a third host material, and the first host material, the second host material, and the third host material are preferably different from each other.
The third emitting layer preferably contains a third emitting compound. The first emitting compound, the second emitting compound, and the third emitting compound may be mutually the same or different, preferably mutually the same.
The third emitting layer preferably contains a compound that emits light having a maximum peak wavelength of 500 nm or less. The third emitting compound is more preferably a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less.
A measurement method of the maximum peak wavelength of the compound is as follows.
The third host material is not particularly limited. For instance, at least one material selected from the group consisting of the first host material and the second host material is usable.
The third emitting compound is not particularly limited. For instance, at least one compound selected from the group consisting of the first emitting compound and the second emitting compound is usable.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first emitting layer and the second emitting layer are preferably in direct contact with each other.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, a layer arrangement in which “the first emitting layer and the second emitting layer are in direct contact with each other” may include one of embodiments (LS1), (LS2), and (LS3) below.
(LS1) An embodiment in which a region containing both the first host material and the second host material is generated in a process of vapor-depositing the compound of the first emitting layer and vapor-depositing the compound of the second emitting layer, and is present on the interface between the first emitting layer and the second emitting layer.
(LS2) An embodiment in which in a case of containing an emitting compound in the first emitting layer and the second emitting layer, a region containing the first host material, the second host material and the emitting compound is generated in a process of vapor-depositing the compound of the first emitting layer and vapor-depositing the compound of the second emitting layer, and is present on the interface between the first emitting layer and the second emitting layer.
(LS3) An embodiment in which in a case of containing an emitting compound in the first emitting layer and the second emitting layer, a region containing the emitting compound, a region containing the first host material or a region containing the second host material is generated in a process of vapor-depositing the compound of the first emitting layer and vapor-depositing the compound of the second emitting layer, and is present on the interface between the first emitting layer and the second emitting layer.
When the organic EL device according to an exemplary arrangement of the exemplary embodiment includes the third emitting layer, preferably, the first emitting layer and the second emitting layer are in direct contact with each other and the second emitting layer and the third emitting layer are in direct contact with each other.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, in a case where “the first emitting layer and the second emitting layer are in direct contact with each other”, a layer arrangement in which “the second emitting layer and the third emitting layer are in direct contact with each other” may include one of embodiments (LS4), (LS5), and (LS6) below.
(LS4) An embodiment in which a region containing both the second host material and the third host material is generated in a process of vapor-depositing the compound of the second emitting layer and vapor-depositing the compound of the third emitting layer, and is present on the interface between the second emitting layer and the third emitting layer.
(LS5) An embodiment in which in a case of containing an emitting compound in the second emitting layer and the third emitting layer, a region containing the second host material, the third host material and the emitting compound is generated in a process of vapor-depositing the compound of the second emitting layer and vapor-depositing the compound of the third emitting layer, and is present on the interface between the second emitting layer and the third emitting layer.
(LS6) An embodiment in which in a case of containing an emitting compound in the second emitting layer and the third emitting layer, a region containing the emitting compound, a region containing the second host material or a region containing the third host material is generated in a process of vapor-depositing the compound of the second emitting layer and vapor-depositing the compound of the third emitting layer, and is present on the interface between the second emitting layer and the third emitting layer.
Also preferably, the organic EL device according to an exemplary embodiment of the exemplary embodiment further includes an interposed layer.
When the organic EL device according to an exemplary arrangement of the exemplary embodiment includes an interposed layer, the interposed layer is preferably disposed between the first emitting layer and the second emitting layer.
The interposed layer is preferably a non-doped layer. The interposed layer is preferably a layer that contains no emitting compound. The interposed layer preferably contains no metal atom.
The interposed layer contains an interposed layer material. The interposed layer material is preferably not an emitting compound.
The interposed layer material, which is not particularly limited, is preferably a material except for the emitting compound.
Examples of the interposed layer material include: 1) a heterocyclic compound such as an oxadiazole derivative, benzimidazole derivative, or phenanthroline derivative; 2) a fused aromatic compound such as a carbazole derivative, anthracene derivative, phenanthrene derivative, pyrene derivative or chrysene derivative; and 3) an aromatic amine compound such as a triarylamine derivative or a fused polycyclic aromatic amine derivative.
The interposed layer material may be one or both of the first host material contained in the first emitting layer and the second host material contained in the second emitting layer.
When the interposed layer contains a plurality of interposed layer materials, the content of each interposed layer material is preferably 10 mass % or more with respect to the total mass of the interposed layer.
The interposed layer contains the interposed layer material preferably at 60 mass % or more, more preferably at 70 mass % or more, still more preferably at 80 mass % or more, still further more preferably at 90 mass % or more, and yet still further more preferably at 95 mass % or more, with respect to the total mass of the interposed layer.
The interposed layer may contain a single type of the interposed layer material or may contain two or more types of the interposed layer material.
When the interposed layer contains two or more types of the interposed layer material, the upper limit of the total of the contents of the two or more types of the interposed layer material is 100 mass %.
It should be noted that the interposed layer of the exemplary embodiment may further contain any other material than the interposed layer material.
The interposed layer may be provided in the form of a single layer or a laminate of two or more layers.
The film thickness of the interposed layer is not particularly limited, however preferably in a range from 3 nm to 15 nm, more preferably from 5 nm to 10 nm per layer.
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the first emitting layer preferably contains the first emitting compound (preferably the first emitting compound that emits light having a maximum peak wavelength of 500 nm or less).
In the organic EL device according to an exemplary arrangement of the exemplary embodiment, the second emitting layer preferably contains the second emitting compound (preferably the second emitting compound that emits light having a maximum peak wavelength of 500 nm or less).
The first emitting compound contained in the first emitting layer and the second emitting compound contained in the second emitting layer are mutually the same or different.
The first emitting compound and the second emitting compound are each independently at least one compound selected from the group consisting of a compound represented by a formula (3) below, a compound represented by a formula (4) below, a compound represented by a formula (5) below, a compound represented by a formula (6) below, a compound represented by a formula (7) below, a compound represented by a formula (8) below, a compound represented by a formula (9) below, and a compound represented by a formula (10) below.
The compound represented by the formula (3) will be described below.
In the formula (3):
In the formula (31):
In the first and second emitting compounds, R901, R902, R903, R904, R905, R906, and R907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the formula (3), two of R301 to R310 are each preferably a group represented by the formula (31).
In an exemplary embodiment, the compound represented by the formula (3) is a compound represented by a formula (33) below.
In the formula (33):
In the formula (31), L301 is preferably a single bond, and L302 and L303 are each preferably a single bond.
In an exemplary embodiment, the compound represented by the formula (3) is represented by a formula (34) or a formula (35) below.
In the formula (34):
In the formula (35):
In the formula (31), at least one of Ar301 or Ar302 is preferably a group represented by a formula (36) below.
In the formulae (33) to (35), at least one of Ar312 or Ar313 is preferably a group represented by the formula (36) below.
In the formulae (33) to (35), at least one of Ar315 or Ar316 is preferably a group represented by the formula (36).
In the formula (36):
At least one of R321 to R327 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (31), preferably, Ar301 is a group represented by the formula (36) and Ar302 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the formulae (33) to (35), preferably, Ar312 is a group represented by the formula (36) and Ar313 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the formulae (33) to (35), preferably, Ar315 is a group represented by the formula (36) and Ar316 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, the compound represented by the formula (3) is represented by a formula (37) below.
In the formula (37):
Specific examples of the compound represented by the formula (3) include compounds shown below.
The compound represented by the formula (4) will be described below.
In the formula (4):
The “aromatic hydrocarbon ring” for the ring A1 and the ring A2 has the same structure as a compound formed by introducing a hydrogen atom to the “aryl group” described above.
Ring atoms of the “aromatic hydrocarbon ring” for the ring A1 and the ring A2 include two carbon atoms on a fused bicyclic structure at the center of the formula (4).
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include a compound formed by introducing a hydrogen atom to the “aryl group” described in the specific example group G1.
The “heterocycle” for the ring A1 and the ring A2 has the same structure as a compound formed by introducing a hydrogen atom to the “heterocyclic group” described above.
Ring atoms of the “heterocycle” for the ring A1 and the ring A2 include two carbon atoms on a fused bicyclic structure at the center of the formula (4).
Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include a compound formed by introducing a hydrogen atom to the “heterocyclic group” described in the specific example group G2.
Rb is bonded to any one of carbon atoms forming the aromatic hydrocarbon ring as the ring A1 or any one of atoms forming the heterocycle as the ring A1.
Rc is bonded to any one of carbon atoms forming the aromatic hydrocarbon ring as the ring A2 or any one of atoms forming the heterocycle as the ring A2.
At least one of Ra, Rb, or Rc is preferably a group represented by a formula (4a) below. More preferably, at least two of Ra, Rb, or Rc are each a group represented by the formula (4a).
[Formula 240]
*-L401-Ar401 (4a)
In the formula (4a):
In the formula (4b):
In an exemplary embodiment, the compound represented by the formula (4) is represented by a formula (42) below.
In the formula (42):
At least one of R401 to R411 is preferably a group represented by the formula (4a). More preferably, at least two of R401 to R411 are each a group represented by the formula (4a).
R404 and R411 are each preferably a group represented by the formula (4a).
In an exemplary embodiment, the compound represented by the formula (4) is a compound formed by bonding a structure represented by a formula (4-1) or a formula (4-2) below to the ring A1.
Further, in an exemplary embodiment, the compound represented by the formula (42) is a compound formed by bonding a structure represented by the formula (4-1) or the formula (4-2) to a ring bonded to R404 to R407.
In the formula (4-1), two bonds * are each independently bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring or a ring atom of the heterocycle as the ring A1 in the formula (4) or bonded to one of R404 to R407 in the formula (42);
In an exemplary embodiment, the compound represented by the formula (4) is a compound represented by a formula (41-3), a formula (41-4) or a formula (41-5) below.
In the formulae (41-3), (41-4), and (41-5):
In an exemplary embodiment, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms as the ring A1 in the 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 as the ring A1 in the formula (41-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
In an exemplary embodiment, the compound represented by the formula (4) or the formula (42) is selected from the group consisting of compounds represented by formulae (461) to (467) below.
In the formulae (461), (462), (463), (464), (465), (466), and (467):
In an exemplary embodiment, at least one combination of adjacent two or more of R401 to R411 in the compound represented by the formula (42) are mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring. This exemplary embodiment will be described in detail below as a compound represented by a formula (45) below.
The compound represented by the formula (45) will be described below.
In the formula (45):
In the formula (45), Rn and Rn+1 (n being an integer selected from 461, 462, 464 to 466, and 468 to 470) are mutually bonded to form a substituted or unsubstituted monocyclic ring or fused ring together with two ring-forming carbon atoms bonded to 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 preferably 3 to 7 atoms, more preferably 5 or 6 atoms.
The number of the above cyclic structures in the compound represented by the formula (45) is, for instance, 2, 3, or 4. The two or more of the cyclic structures may be present on the same benzene ring on the basic skeleton represented by the formula (45) or may be present on different benzene rings. For instance, when three cyclic structures are present, each of the cyclic structures may be present on the corresponding one of the three benzene rings of the formula (45).
Examples of the above cyclic structures in the compound represented by the formula (45) include structures represented by formulae (451) to (460) below.
In the formulae (451) to (457):
In the formulae (458) to (460):
In the formula (45), preferably, 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 forming no cyclic structure.
(i) A substituent, if present, for a cyclic structure formed by Rn and Rn+1 in the formula (45), (ii) R461 to R471 forming no cyclic structure in the formula (45), and (iii) R4501 to R4514, R4515 to R4525 in the formulae (451) to (460) are preferably each independently a 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) below.
In the formulae (461) to (464):
In the first emitting compound and the second emitting compound, R901 to R907 are as defined above.
In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-1) to (45-6) below.
In the formulae (45-1) to (45-6):
In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-7) to (45-12) below.
In the formulae (45-7) to (45-12):
In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-13) to (45-21) below.
In the formulae (45-13) to (45-21):
When the cyclic structure g or the cyclic structure h further has a substituent, examples of the substituent include a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a group represented by the formula (461), a group represented by the formula (463), and a group represented by the formula (464).
In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-22) to (45-25) below.
In the formulae (45-22) to (45-25):
In an exemplary embodiment, the compound represented by the formula (45) is represented by a formula (45-26) below.
In the formula (45-26):
Specific examples of the compound represented by the formula (4) include compounds shown below. In the specific examples below, Ph represents a phenyl group, and D represents a deuterium atom.
The compound represented by the formula (5) will be described below. The compound represented by the formula (5) corresponds to a compound represented by the formula (41-3).
In the formula (5):
“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 or R511 to R517 are each a group represented by —N(R906)(R907).
In an exemplary embodiment, R501 to R507 and R511 to R517 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, the compound represented by the formula (5) is a compound represented by a formula (52) below.
In the formula (52):
In an exemplary embodiment, the compound represented by the formula (5) is a compound represented by a formula (53) below.
In the formula (53), R551, R552 and R561 to R564 each independently represent the same as R551, R552 and R561 to R564 in the formula (52).
In an exemplary embodiment, R561 to R564 in the formulae (52) and (53) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).
In an exemplary embodiment, R521 and R522 in the formula (5) and R551 and R552 in the formulae (52) and (53) are each a hydrogen atom.
In an exemplary embodiment, the substituent for the “substituted or unsubstituted” group in the formulae (5), (52) and (53) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Specific examples of the compound represented by the formula (5) include compounds shown below.
The compound represented by the formula (6) will be described below.
In the formula (6):
The ring a, ring b and ring c 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 a fused bicyclic structure formed of a boron atom and two nitrogen atoms at the center of the formula (6).
The “aromatic hydrocarbon ring” for the rings a, b, and c has the same structure as a compound formed by introducing a hydrogen atom to the “aryl group” described above.
Ring atoms of the “aromatic hydrocarbon ring” for the ring a include three carbon atoms on the fused bicyclic structure at the center of the formula (6).
Ring atoms of the “aromatic hydrocarbon ring” for the rings b and c include two carbon atoms on the fused bicyclic structure at the center of the formula (6).
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include a compound formed by introducing a hydrogen atom to the “aryl group” described in the specific example group G1.
The “heterocycle” for the rings a, b, and c has the same structure as a compound formed by introducing a hydrogen atom to the “heterocyclic group” described above.
Ring atoms of the “heterocycle” for the ring a include three carbon atoms on the fused bicyclic structure at the center of the formula (6). Ring atoms of the “heterocycle” for the rings b and c include two carbon atoms on the fused bicyclic structure at the center of the formula (6). Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include a compound formed by introducing a hydrogen atom to the “heterocyclic group” described in the specific example group G2.
R601 and R602 may be each independently bonded with the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle. The “heterocycle” in this arrangement includes a nitrogen atom on the fused bicyclic structure at the center of the formula (6). The heterocycle in the above arrangement optionally includes a hetero atom other than the nitrogen atom. R601 and R602 being bonded with the ring a, ring b, or ring c specifically means that atoms forming R601 and R602 are bonded with atoms forming the ring a, ring b, or ring c. For instance, R601 may be bonded with the ring a to form a bicyclic (or tri-or-more cyclic) fused nitrogen-containing heterocycle, in which the ring including R601 and the ring a 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 ring b, R602 bonded with the ring a, and R602 bonded with the ring c.
In an exemplary embodiment, the ring a, ring b and ring c in the formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
In an exemplary embodiment, the ring a, ring b and ring c in the 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 the formula (6) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, the compound represented by the formula (6) is a compound represented by a formula (62) below.
In the formula (62):
R601A and R602A in the formula (62) are groups corresponding to R601 and R602 in the formula (6), respectively.
For instance, R601A and R611 are optionally bonded with each other to form a bicyclic (or tri-or-more cyclic) fused nitrogen-containing heterocycle, in which the ring including R601A and R611 and a benzene ring corresponding to the ring a 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.
Optionally, at least one combination of adjacent two or more of R611 to R621 are mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring.
For instance, R611 and R612 are optionally mutually bonded to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring, benzothiophene ring or the like is 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 the formula (62) is a compound represented by a formula (63) below.
In the formula (63):
R631 is optionally 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 ring a are fused. Specific examples of the nitrogen-containing heterocycle include a compound corresponding to a 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
In an exemplary embodiment, the compound represented by the formula (63) is a compound represented by a formula (63A) below.
In the formula (63A):
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 the formula (63) is a compound represented by a formula (63B) below.
In the formula (63B):
In an exemplary embodiment, the compound represented by the formula (63) is a compound represented by a formula (63B′) below.
In the formula (63B′), R672 to R675 each independently represent the same as R672 to R675 in the 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 the formula (63) is a compound represented by a formula (63C) below.
In the formula (63C):
In an exemplary embodiment, the compound represented by the formula (63) is a compound represented by a formula (63C′) below.
In the formula (63C′), R683 to R686 each independently represent the same as R683 to R686 in the 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 carbon atoms.
The compound represented by the formula (6) is producible by initially bonding the ring a, ring b and ring c with linking groups (a group including N—R601 and a group including N—R602) to form an intermediate (first reaction), and bonding the ring a, ring b and ring c with a linking group (a group including a boron atom) to form a final product (second reaction). In the first reaction, an amination reaction (e.g. Buchwald-Hartwig reaction) is applicable. In the second reaction, Tandem Hetero-Friedel-Crafts Reactions or the like is applicable.
Specific examples of the compound represented by the formula (6) are shown below. It should however be noted that these specific examples are merely exemplary and do not limit the compound represented by the formula (6).
The compound represented by the formula (7) will be described below.
In the formula (7):
In the formula (7), each of the ring p, ring q, ring r, ring s, and ring t 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 the formula (72) or the formula (73) representing the ring r, m1=0 or m2=0 is satisfied.
In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-1) to (71-6) below.
In the formulae (71-1) to (71-6), R701, X7, Ar701, Ar702, L701, m1 and m3 respectively represent the same as R701, X7, Ar701, Ar702, L701, m1 and m3 in the formula (7).
In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-11) to (71-13) below.
In the formulae (71-11) to (71-13), R701, X7, Ar701, Ar702, L701, m1, m3 and m4 respectively represent the same as R701, X7, Ar701, Ar702, L701, m1, m3 and m4 in the formula (7).
In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-21) to (71-25) below.
In the formulae (71-21) to (71-25), R701, X7, Ar701, Ar702, L701, m1 and m4 respectively represent the same as R701, X7, Ar701, Ar702, L701, m1 and m4 in the formula (7).
In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-31) to (71-33) below.
In the formulae (71-31) to (71-33), R701, X7, Ar701, Ar702, L701, and m2 to m4 respectively represent the same as R701, X7, Ar701, Ar702, L701, and m2 to m4 in the formula (7).
In 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 the formula (7) include compounds shown below.
The compound represented by the formula (8) will be described below.
In the formula (8):
At least one of R801 to R804 not forming the divalent group represented by the formula (82) or R811 to R814 is a monovalent group represented by a formula (84) below;
In the formula (84):
In the formula (8), the positions for the divalent group represented by the formula (82) and the divalent group represented by the formula (83) to be formed are not specifically limited but the divalent groups may be formed at any possible positions on R801 to R808.
In an exemplary embodiment, the compound represented by the formula (8) is represented by any one of formulae (81-1) to (81-6) below.
In the formulae (81-1) to (81-6):
In an exemplary embodiment, the compound represented by the formula (8) is represented by any one of formulae (81-7) to (81-18) below.
In the formulae (81-7) to (81-18):
R801 to R808 not forming the divalent group represented by the formula (82) or (83) and not being the monovalent group represented by the formula (84), and R811 to R814 and R821 to R824 not being the monovalent group represented by the formula (84) are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
The monovalent group represented by the formula (84) is preferably represented by a formula (85) or (86) below.
In the formula (85):
In the formula (86):
In the formula (87):
Specific examples of the compound represented by the formula (8) include compounds shown below as well as the compounds disclosed in WO 2014/104144.
The compound represented by the formula (9) will be described below.
In the formula (9):
In the formula (92):
At least one of the ring A91 or the ring A92 is bonded to * in the structure represented by the formula (92). In other words, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the ring A91 in an exemplary embodiment are bonded to the * in the structure represented by the formula (92). Further, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the ring A92 in an exemplary embodiment are bonded to * in the structure represented by the formula (92).
In an exemplary embodiment, a group represented by a formula (93) below is bonded to one or both of the ring A91 and the ring A92.
In the formula (93):
In an exemplary embodiment, in addition to the ring A91, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the ring A92 are bonded to * in the structure represented by the formula (92). In this case, the structures represented by the 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 cyclic structures 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 cyclic structure 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 the formula (9) include compounds shown below.
The compound represented by the formula (10) will be described below.
In the formula (10):
In an exemplary embodiment, Ar1001 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, the ring Ax3 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 the formula (10) include compounds shown below.
In an exemplary embodiment, the emitting layer contains, as at least one of the first emitting compound or the second emitting compound, at least one compound selected from the group consisting of a compound represented by the formula (4), a compound represented by the formula (5), a compound represented by the formula (7), a compound represented by the formula (8), a compound represented by the formula (9) and a compound represented by a formula (63a) below.
In the formula (63a):
In an exemplary embodiment, the compound represented by the formula (4) is a compound represented by the formula (41-3), the formula (41-4), or the formula (41-5), the ring A1 in the formula (41-5) being a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, or a substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms.
In an exemplary embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formulae (41-3), (41-4) and (41-5) is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring; and
In an exemplary embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formula (41-3), (41-4) or (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring; and
In an exemplary embodiment, the compound represented by the formula (4) is selected from the group consisting of a compound represented by a formula (461) below, a compound represented by a formula (462) below, a compound represented by a formula (463) below, a compound represented by a formula (464) below, a compound represented by a formula (465) below, a compound represented by a formula (466) below, and a compound represented by a formula (467) below.
In the formulae (461) to (467):
In an exemplary embodiment, R421 to R427 and R440 to R448 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In 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 the formula (41-3) is a compound represented by a formula (41-3-1) below.
In the formula (41-3-1), R423, R425, R426, R442, R444 and R445 each independently represent the same as R423, R425, R426, R442, R444 and R445 in the formula (41-3).
In an exemplary embodiment, the compound represented by the formula (41-3) is a compound represented by a formula (41-3-2) below.
In the formula (41-3-2), R421 to R427 and R440 to R448 each independently represent the same as R421 to R427 and R440 to R448 in the formula (41-3); 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 the formula (41-3-2) are each a group represented by —N(R906)(R907).
In an exemplary embodiment, the compound represented by the formula (41-3-2) is a compound represented by a formula (41-3-3) below.
In the formula (41-3-3), R421 to R424, R440 to R443, R447, and R448 each independently represent the same as R421 to R424, R440 to R443, R447, and R448 in the formula (41-3); and RA, RB, RC, and RD are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
In an exemplary embodiment, the compound represented by the formula (41-3-3) is a compound represented by a formula (41-3-4) below.
In the formula (41-3-4), R447, R448, RA, RB, RC and RD each independently represent the same as R447, R448, RA, RB, RC and RD in the formula (41-3-3).
In 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 “the 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;
In an exemplary embodiment, the substituent for “the 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 “the 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.
The arrangement of the organic EL device will be further described below. It should be noted that the reference numerals are occasionally 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. Further, 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 indium tin oxide (ITO), 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 AILi) 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, the inkjet method, or the like is 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, 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 AILi) including the alkali metal or the alkaline earth metal, a 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 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) is 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 electron transporting layer is a layer containing a highly electron-transporting substance. For the electron transporting layer, 1) a metal complex such as an aluminum complex, beryllium complex, and zinc complex, 2) a hetero aromatic compound such as imidazole derivative, benzimidazole derivative, azine derivative, carbazole derivative, and phenanthroline derivative, and 3) a high polymer compound are usable. Specifically, as a low-molecule organic compound, a metal complex such as Alq, tris(4-methyl-8-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. The above-described substances mostly have an electron mobility of 10−6 cm2/Vs or more. It should be noted that any other substance than the above substance may be used for the electron transporting layer as long as the substance exhibits a higher electron transportability than the hole transportability. The electron transporting layer may be provided in the form of a single layer or a laminate of two or more layers of the above substance(s).
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.
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 hetero aromatic compound) of the substance forming the electron transporting layer are usable. As the electron donor, any substance exhibiting electron donating property to the organic compound is usable. Specifically, the electron donor is preferably alkali metal, alkaline earth metal and rare earth metal such as lithium, cesium, magnesium, calcium, erbium and ytterbium. The electron donor is also preferably alkali metal oxide and alkaline earth metal oxide such as lithium oxide, calcium oxide, and barium oxide. Moreover, a Lewis base such as magnesium oxide is usable. Further, the organic compound such as tetrathiafulvalene (abbreviation: TTF) is usable.
A method of forming each layer of the organic EL device according to an exemplary arrangement of 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.
The film thickness of each of the organic layers of the organic EL device according to an exemplary arrangement of 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 an excessively small film thickness is likely to cause defects (e.g. pin holes) and an excessively large thickness leads to the necessity of applying high voltage and consequent reduction in efficiency.
An electronic device according to a second exemplary embodiment is installed with one of the organic EL devices according to the exemplary embodiment. Examples of the electronic device include a display device and a light-emitting unit. Examples of the display device include a display component (e.g., an organic EL panel module), TV, mobile phone, tablet and personal computer. Examples of the light-emitting unit include an illuminator and a vehicle light.
The scope of the invention is not limited 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 number of emitting layers is not limited to two, and more than two emitting layers may be layered. When the organic EL device includes more than two emitting layers, it is only necessary that at least two of the emitting layers should satisfy the requirements mentioned 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.
For instance, a blocking layer may be provided adjacent to at least one of a side of the emitting layer close to the anode or a side of the emitting layer close to the cathode. The blocking layer is preferably provided in contact with the emitting layer to block at least one of holes, electrons, or excitons.
For instance, when the blocking layer is provided in contact with the side of the emitting layer close to the cathode, the blocking layer permits transport of electrons, and blocks holes from reaching a layer provided closer to the cathode (e.g., the electron transporting layer) beyond the blocking layer. When the organic EL device includes the electron transporting layer, the blocking layer is preferably interposed between the emitting layer and the electron transporting layer.
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 interposed between the emitting layer and the hole transporting layer.
Alternatively, the blocking layer may be provided adjacent to the emitting layer so that the excitation energy does not leak out from the emitting layer toward neighboring layer(s). The blocking layer blocks excitons generated in the emitting layer from being transferred to a layer(s) (e.g., the electron transporting layer and the hole transporting layer) closer to the electrode(s) beyond the blocking layer.
The emitting layer is preferably bonded with the blocking layer.
Specific structure, shape and the like of the components in the invention may be designed in any manner as long as an object of the invention can be achieved.
Structures of the compounds represented by the formula (1000) according to Examples are shown below.
Structures of the compounds represented by the formula (2) according to Examples are shown below.
Structures of other compounds used for producing organic EL devices according to Examples and Comparatives are shown below.
The organic EL devices were produced and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, produced by Geomatec Co., Ltd.) having an ITO 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.
After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum deposition apparatus. Firstly, a compound HT1 and a compound HA1 were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA1 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After forming the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
A compound HT2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer) (EBL).
A compound BH1-1 (first host material (BH)) and a compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
A compound BH2-1 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
A compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer) (HBL).
A compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
A device arrangement of the organic EL device in Example 1 is roughly shown as follows.
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. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1 or BH2-1) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL device in Example 2 was produced in the same manner as in Example 1 except that the compound BH1-1 (first host material) in the first emitting layer was changed to a compound shown in Table 1.
The organic EL device in Example 3 was produced in the same manner as in Example 1 except that the compound BH1-1 (first host material) in the first emitting layer was changed to a compound shown in Table 1 and the compound BH2-1 (second host material) in the second emitting layer was changed to a compound shown in Table 1.
The organic EL device in Comparative 1 was produced in the same manner as in Example 1 except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 1.
The organic EL device in Comparative 2 was produced in the same manner as in Example 2 except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 1.
The organic EL device in Comparative 3 was produced in the same manner as in Example 3 except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 1.
The organic EL devices produced in Examples 1 to 3 and Comparatives 1 to 3 were evaluated as follows. Table 1 shows the evaluation results.
Voltage was applied to the organic EL device such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
EQE (relative value) (unit: %) was calculated based on the measurement value of EQE of each example and a numerical formula (Numerical Formula 100) below.
EQE(Relative Value)=(EQE of Example X/EQE of Comparative X)×100 (Numerical Formula 100)
where, X is 1, 2 or 3.
Voltage was applied to the produced organic EL device such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured. The luminance intensity was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.).
LT95 (relative value) (unit: %) was calculated based on the measurement value of LT95 of each example and a numerical formula (Numerical Formula 101) below.
LT95(Relative Value)=(LT95 of Example X/LT95 of Comparative X)×100 (Numerical Formula 101)
where X is 1, 2 or 3.
As shown in Table 1, the organic EL device in Example 1 including the first emitting layer that contained the first compound as the first host material and the second emitting layer that contained the second compound as the second host material emitted light with higher luminous efficiency than the organic EL device in Comparative 1 only including the second emitting layer. The organic EL device in Example 2 had a longer lifetime than the organic EL device in Comparative 2. The organic EL device in Example 3 had a higher efficiency and longer lifetime than the organic EL device in Comparative 3.
A measurement target compound was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution. Using a fluorescence spectrometer (spectrophotofluorometer F-7000 produced by Hitachi High-Tech Science Corporation), the toluene solution of the measurement target compound was excited at 390 nm, where a maximum fluorescence peak wavelength λ (unit: nm) was measured.
The maximum fluorescence peak wavelength A of the compound BD1 was 458 nm.
Structures of the compounds represented by the formula (1001) according to Examples are shown below.
Structures of the compounds represented by the formula (2) according to Examples are shown below.
Structures of other compounds used for producing organic EL devices according to Examples and Comparatives are shown below.
The organic EL devices were produced and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, produced by Geomatec Co., Ltd.) having an ITO 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.
After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum deposition apparatus. Firstly, the compound HT1 and the compound HA1 were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA1 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After forming the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
The compound HT2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer) (EBL).
A compound BH1-1J (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
A compound BH2-1J (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer) (HBL).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
A device arrangement of the organic EL device in Example 1A is roughly shown as follows.
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. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1 or BH2-1J) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL devices in Examples 2A to 5A were produced in the same manner as in Example 1A except that the compound BH1-1J (first host material) in the first emitting layer and the compound BH2-1J (second host material) in the second emitting layer were changed to those shown in Table 2.
The organic EL device in Comparative 1A was produced in the same manner as in Example 1A except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 2.
The organic EL device in Comparative 2A was produced in the same manner as in Example 2A except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 2.
The organic EL device in Comparative 3A was produced in the same manner as in Example 3A except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 2.
The organic EL device in Comparative 4A was produced in the same manner as in Example 4A except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 2.
The organic EL device in Comparative 5A was produced in the same manner as in Example 5A except that the second emitting layer having a film thickness of 25 nm was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 2.
Evaluation of Organic EL Devices The organic EL devices produced in Examples 1A to 5A and Comparatives 1A to 5A were evaluated as follows. Table 2 shows the evaluation results.
Voltage was applied to the organic EL device such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
EQE (relative value) (unit: %) was calculated based on the measurement value of EQE of each example and a numerical formula (Numerical Formula 100A) below.
EQE(Relative Value)=(EQE of Example XA/EQE of Comparative XA)×100 (Numerical Formula 100A)
where, X is 1, 2, 3, 4, or 5.
Voltage was applied to the produced organic EL device such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured. The luminance intensity was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.).
LT95 (relative value) (unit: %) was calculated based on the measurement value of LT95 of each example and a numerical formula (Numerical Formula 101A) below.
LT95(Relative Value)=(LT95 of Example XA/LT95 of Comparative XA)×100 (Numerical Formula 101A)
where, X is 1, 2, 3, 4, or 5.
As shown in Table 2, the organic EL devices in Examples 1A to 5A, each of which included the first emitting layer that contained the first compound as the first host material and the second emitting layer that contained the second compound as the second host material, emitted light with higher luminous efficiency than the organic EL devices in Comparatives 1A to 5A each including only the second emitting layer. The organic EL devices in Examples 1A to 5A had a longer lifetime than the organic EL devices in Comparatives 1A to 5A.
A measurement target compound was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution. Using a fluorescence spectrometer (spectrophotofluorometer F-7000 produced by Hitachi High-Tech Science Corporation), the toluene solution of the measurement target compound was excited at 390 nm, where a maximum fluorescence peak wavelength A (unit: nm) was measured.
The maximum fluorescence peak wavelength A of the compound BD1 was 458 nm.
Structures of the compounds represented by the formula (1002) according to Examples are shown below.
Structures of the compounds represented by the formula (2) according to Examples are shown below.
Structures of other compounds used for producing organic EL devices according to Examples and Comparatives are shown below.
The organic EL devices were produced and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, produced by Geomatec Co., Ltd.) having an ITO 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.
After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum deposition apparatus. Firstly, the compound HT1 and the compound HA1 were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA1 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After forming the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
The compound HT2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer) (EBL).
A compound BH1-1P (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
A compound BH2-1P (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer) (HBL).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
A device arrangement of the organic EL device in Example 1B is roughly shown as follows.
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. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1P or BH2-1P) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL devices in Examples 2B to 8B were produced in the same manner as in Example 1B except that the compound BH1-1P (first host material) in the first emitting layer and the compound BH2-1P (second host material) in the second emitting layer were changed to those shown in Table 3.
The organic EL device in Comparative 1B was produced in the same manner as in Example 1B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL device in Comparative 2B was produced in the same manner as in Example 2B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL device in Comparative 3B was produced in the same manner as in Example 3B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL device in Comparative 4B was produced in the same manner as in Example 4B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL device in Comparative 5B was produced in the same manner as in Example 5B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL device in Comparative 6B was produced in the same manner as in Example 6B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL device in Comparative 7B was produced in the same manner as in Example 7B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL device in Comparative 8B was produced in the same manner as in Example 8B except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 3.
The organic EL devices produced in Examples 1B to 8B and Comparatives 1B to 8B were evaluated as follows. Table 3 shows the evaluation results.
External Quantum Efficiency EQE Voltage was applied to the organic EL device such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
EQE (relative value) (unit: %) was calculated based on the measurement value of EQE of each example and a numerical formula (Numerical Formula 100B) below.
EQE(Relative Value)=(EQE of Example XB/EQE of Comparative XB)×100 (Numerical Formula 100B)
where, X is 1, 2, 3, 4, 5, 6, 7, or 8.
Voltage was applied to the produced organic EL device such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured. The luminance intensity was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.).
LT95 (relative value) (unit: %) was calculated based on the measurement value of LT95 of each example and a numerical formula (Numerical Formula 101B) below.
LT95(Relative Value)=(LT95 of Example XB/LT95 of Comparative XB)×100 (Numerical Formula 101B)
where, X is 1, 2, 3, 4, 5, 6, 7, or 8.
As shown in Table 3, the organic EL devices in Examples 1B to 7B, each of which included the first emitting layer that contained the first compound as the first host material and the second emitting layer that contained the second compound as the second host material, had a longer lifetime than the organic EL devices in Comparatives 1B to 7B each including only the second emitting layer. Further, the organic EL devices in Examples 1B to 3B and Examples 5B to 7B emitted light with higher luminous efficiency than the organic EL devices in Comparatives 1B to 3B and Comparatives 5B to 7B. The organic EL device in Example 8B had a higher efficiency and longer lifetime than the organic EL device in Comparative 8B.
A measurement target compound was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution. Using a fluorescence spectrometer (spectrophotofluorometer F-7000 produced by Hitachi High-Tech Science Corporation), the toluene solution of the measurement target compound was excited at 390 nm, where a maximum fluorescence peak wavelength A (unit: nm) was measured.
The maximum fluorescence peak wavelength A of the compound BD1 was 458 nm.
Structures of the first compound according to Examples are shown below.
A Structure of the second compound according to Examples is shown below.
Structures of other compounds used for producing organic EL devices according to Examples and Comparatives are shown below.
The organic EL devices were produced and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, produced by Geomatec Co., Ltd.) having an ITO 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.
After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum deposition apparatus. Firstly, the compound HT1 and the compound HA1 were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA1 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After forming the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
The compound HT2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer) (EBL).
A compound BH1-1K (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
A compound BH2-1K (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer) (HBL).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
A device arrangement of the organic EL device in Example 1C is roughly shown as follows.
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. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1K or BH2-1K) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL device in Example 2C was produced in the same manner as in Example 1C except that the compound BH1-1K (first host material) in the first emitting layer was changed to a compound shown in Table 4.
The organic EL device in Comparative 1C was produced in the same manner as in Example 1C except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 4.
The organic EL device in Comparative 2C was produced in the same manner as in Example 2C except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 4.
The organic EL devices produced in Examples 1C to 2C and Comparatives 1C to 2C were evaluated as follows. Table 4 shows the evaluation results.
Voltage was applied to the organic EL device such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
EQE (relative value) (unit: %) was calculated based on the measurement value of EQE of each example and a numerical formula (Numerical Formula 1000) below.
EQE(Relative Value)=(EQE of Example XC/EQE of Comparative XC)×100 (Numerical Formula 1000),
Voltage was applied to the produced organic EL device such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured. The luminance intensity was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.).
LT95 (relative value) (unit: %) was calculated based on the measurement value of LT95 of each example and a numerical formula (Numerical Formula 101C) below.
LT95(Relative Value)=(LT95 of Example XC/LT95 of Comparative XC)×100 (Numerical Formula 101C)
where, X is 1 or 2.
As shown in Table 4, the organic EL devices in Examples 1C to 2C, each of which included the first emitting layer that contained the first compound as the first host material and the second emitting layer that contained the second compound as the second host material, emitted light with higher luminous efficiency than the organic EL devices in Comparatives 1C to 2C each including only the second emitting layer. The organic EL devices in Examples 1C to 2C had a longer lifetime than the organic EL devices in Comparatives 1C to 2C.
A measurement target compound was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution. Using a fluorescence spectrometer (spectrophotofluorometer F-7000 produced by Hitachi High-Tech Science Corporation), the toluene solution of the measurement target compound was excited at 390 nm, where a maximum fluorescence peak wavelength A (unit: nm) was measured.
The maximum fluorescence peak wavelength A of the compound BD1 was 458 nm.
Structures of the compounds represented by the formula (1005) according to Examples are shown below.
A Structure of the compound represented by the formula (2) according to Examples is shown below.
Structures of other compounds used for producing organic EL devices according to Examples and Comparatives are shown below.
The organic EL devices were produced and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, produced by Geomatec Co., Ltd.) having an ITO 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.
After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum deposition apparatus. Firstly, the compound HT1 and the compound HA1 were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA1 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After forming the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
The compound HT2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer) (EBL).
A compound BH1-1Q (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
A compound BH2-1Q (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer) (HBL).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
A device arrangement of the organic EL device in Example 1D is roughly shown as follows.
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. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1Q or BH2-1 Q) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL device in Example 2D was produced in the same manner as in Example 1D except that the compound BH1-1Q (first host material) in the first emitting layer was changed to a compound shown in Table 5.
The organic EL device in Comparative 1 D was produced in the same manner as in Example 1 D except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 5.
The organic EL device in Comparative 2D was produced in the same manner as in Example 2D except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 5.
The organic EL devices produced in Examples 1 D to 2D and Comparatives 1 D to 2D were evaluated as follows. Table 5 shows the evaluation results.
Voltage was applied to the organic EL device such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
EQE (relative value) (unit: %) was calculated based on the measurement value of EQE of each example and a numerical formula (Numerical Formula 100D) below.
EQE(Relative Value)=(EQE of Example XD/EQE of Comparative XD)×100 (Numerical Formula 100D),
Voltage was applied to the produced organic EL device such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured. The luminance intensity was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.).
LT95 (relative value) (unit: %) was calculated based on the measurement value of LT95 of each example and a numerical formula (Numerical Formula 101 D) below.
LT95(Relative Value)=(LT95 of Example XD/LT95 of Comparative XD)×100 (Numerical Formula 101D)
where X is 1 or 2.
As shown in Table 5, the organic EL devices in Examples 1 D to 2D, each of which included the first emitting layer that contained the first compound as the first host material and the second emitting layer that contained the second compound as the second host material, emitted light with higher luminous efficiency than the organic EL devices in Comparatives 1 D to 2D each including only the second emitting layer. The organic EL devices in Examples 1 D to 2D had a longer lifetime than the organic EL devices in Comparatives 1 D to 2D.
A measurement target compound was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution. Using a fluorescence spectrometer (spectrophotofluorometer F-7000 produced by Hitachi High-Tech Science Corporation), the toluene solution of the measurement target compound was excited at 390 nm, where a maximum fluorescence peak wavelength A (unit: nm) was measured.
The maximum fluorescence peak wavelength A of the compound BD1 was 458 nm.
Structures of the compounds represented by the formula (1006) according to Examples are shown below.
Structures of the compounds represented by the formula (2) according to Examples are shown below.
Structures of other compounds used for producing organic EL devices according to Examples and Comparatives are shown below.
The organic EL devices were produced and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, produced by Geomatec Co., Ltd.) having an ITO 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.
After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum deposition apparatus. Firstly, the compound HT1 and the compound HA1 were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA1 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After forming the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
The compound HT2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer) (EBL).
A compound BH1-1R (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
A compound BH2-1R (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer) (HBL).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
A device arrangement of the organic EL device in Example 1E is roughly shown as follows.
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. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1R or BH2-1R) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL devices in Examples 2E to 4E were produced in the same manner as in Example 1E except that the compound BH1-1R (first host material) in the first emitting layer and the compound BH2-1R (second host material) in the second emitting layer were changed to those shown in Table 6.
The organic EL device in Comparative 1E was produced in the same manner as in Example 1E except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 6.
The organic EL device in Comparative 2E was produced in the same manner as in Example 2E except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 6.
The organic EL device in Comparative 3E was produced in the same manner as in Example 3E except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 6.
The organic EL device in Comparative 4E was produced in the same manner as in Example 4E except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 6.
The organic EL devices produced in Examples 1E to 4E and Comparatives 1E to 4E were evaluated as follows. Table 6 shows the evaluation results.
Voltage was applied to the organic EL device such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
EQE (relative value) (unit: %) was calculated based on the measurement value of EQE of each example and a numerical formula (Numerical Formula 100E) below.
EQE(Relative Value)=(EQE of Example XE/EQE of Comparative XE)×100 (Numerical Formula 100E),
Voltage was applied to the produced organic EL device such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured. The luminance intensity was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.).
LT95 (relative value) (unit: %) was calculated based on the measurement value of LT95 of each example and a numerical formula (Numerical Formula 101E) below.
LT95(Relative Value)=(LT95 of Example XE/LT95 of Comparative XE)×100 (Numerical Formula 101E)
where, X is 1, 2, 3, or 4.
As shown in Table 6, the organic EL devices in Examples 1E to 4E, each of which included the first emitting layer that contained the first compound as the first host material and the second emitting layer that contained the second compound as the second host material, emitted light with higher luminous efficiency than the organic EL devices in Comparatives 1E to 4E each including only the second emitting layer. The organic EL devices in Examples 1E to 4E had a longer lifetime than the organic EL devices in Comparatives 1E to 4E.
A measurement target compound was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution. Using a fluorescence spectrometer (spectrophotofluorometer F-7000 produced by Hitachi High-Tech Science Corporation), the toluene solution of the measurement target compound was excited at 390 nm, where a maximum fluorescence peak wavelength A (unit: nm) was measured.
The maximum fluorescence peak wavelength A of the compound BD1 was 458 nm.
Structures of the compound represented by the formula (1007) and the compound represented by the formula (2) according to Examples are shown below.
Structures of other compounds used for producing organic EL devices according to Examples and Comparatives are shown below.
The organic EL devices were produced and evaluated as follows.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, produced by Geomatec Co., Ltd.) having an ITO 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.
After the glass substrate having the transparent electrode line was cleaned, the glass substrate was mounted on a substrate holder of a vacuum deposition apparatus. Firstly, the compound HT1 and the compound HA1 were co-deposited on a surface of the glass substrate where the transparent electrode line was provided in a manner to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer (HI). The ratios of the compound HT1 and the compound HA1 in the hole injecting layer were 97 mass % and 3 mass %, respectively.
After forming the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick first hole transporting layer (HT).
The compound HT2 was vapor-deposited on the first hole transporting layer to form a 10-nm-thick second hole transporting layer (also referred to as an electron blocking layer) (EBL).
A compound BH1-1S (first host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
A compound BH2-1 S (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
The compound ET1 was vapor-deposited on the second emitting layer to form a 10-nm-thick first electron transporting layer (also referred to as a hole blocking layer) (HBL).
The compound ET2 was vapor-deposited on the first electron transporting layer to form a 15-nm-thick second electron transporting layer (ET).
LiF was vapor-deposited on the second electron transporting layer to form a 1-nm-thick electron injecting layer.
Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
A device arrangement of the organic EL device in Example 1E is roughly shown as follows.
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. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1S or BH2-1S) and the compound BD1 in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
The organic EL device in Comparative 1F was produced in the same manner as in Example 1F except that a 25-nm-thick second emitting layer was formed as the emitting layer and the second emitting layer was formed on the second hole transporting layer without forming the first emitting layer, as shown in Table 7.
The organic EL devices produced in Example 1F and Comparative 1F were evaluated as follows. Table 7 shows the evaluation results.
Voltage was applied to the organic EL device such that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
EQE (relative value) (unit: %) was calculated based on the measurement value of EQE of each example and a numerical formula (Numerical Formula 100F) below.
EQE(Relative Value)=(EQE of Example 1F/EQE of Comparative 1F)×100 (Numerical Formula 100F)
Voltage was applied to the produced organic EL device such that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured. The luminance intensity was measured by a spectroradiometer CS-2000 (produced by Konica Minolta, Inc.).
LT95 (relative value) (unit: %) was calculated based on the measurement value of LT95 of each example and a numerical formula (Numerical Formula 101F) below.
LT95(Relative Value)=(LT95 of Example 1F/LT95 of Comparative 1F)×100 (Numerical Formula 101F)
As shown in Table 7, the organic EL device in Example 1F that included the first emitting layer that contained the first compound as the first host material and the second emitting layer that contained the second compound as the second host material had a higher efficiency and longer lifetime than the organic EL device in Comparative 1F including only the second emitting layer.
A measurement target compound was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution. Using a fluorescence spectrometer (spectrophotofluorometer F-7000 produced by Hitachi High-Tech Science Corporation), the toluene solution of the measurement target compound was excited at 390 nm, where a maximum fluorescence peak wavelength A (unit: nm) was measured.
The maximum fluorescence peak wavelength A of the compound BD1 was 458 nm.
1, 1A . . . organic EL device, 2 . . . substrate, 3 . . . anode, 4 . . . cathode, 51 . . . first emitting layer, 52 . . . second emitting layer, 6 . . . hole injecting layer, 7 . . . hole transporting layer, 8 . . . electron transporting layer, 9 . . . electron injecting layer
| Number | Date | Country | Kind |
|---|---|---|---|
| 2021-038257 | Mar 2021 | JP | national |
| 2021-038296 | Mar 2021 | JP | national |
| 2021-038517 | Mar 2021 | JP | national |
| 2021-038518 | Mar 2021 | JP | national |
| 2021-038611 | Mar 2021 | JP | national |
| 2021-038612 | Mar 2021 | JP | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/JP2022/010742 | 3/10/2022 | WO |
