Organic electroluminescence element and electronic device
A stacked OLED design with distinct host materials and a phenanthroline compound in the cathode-side layer addresses triplet-triplet fusion issues, enhancing efficiency and longevity.
Patent Information
- Application Number
- JP2024144576
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2020-02-14
- Filing Date
- 2024-08-26
- Publication Date
- 2025-12-09
- Estimated Expiration
- 2041-02-10
AI Technical Summary
Organic electroluminescent elements (OLEDs) with phenanthroline compounds in intermediate layers experience reduced device life and luminous efficiency due to triplet-triplet fusion phenomena.
Incorporating a stacked light-emitting unit with distinct light-emitting layers containing different host materials, where the triplet energy of the first host material exceeds that of the second, and using a phenanthroline compound in the cathode-side organic layer, to manage exciton formation and enhance efficiency.
Improves OLED performance by extending device life and enhancing luminous efficiency through controlled exciton generation and layer design.
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Abstract
Description
[Technical Field]
[0001] The present invention relates to an organic electroluminescence element and an electronic device. [Background technology]
[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays such as those for mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The injected holes and electrons then recombine in the light-emitting layer to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons at a rate of 75%. In order to improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Documents 1 to 6). For example, Patent Documents 6 and 7 discuss stacking multiple light-emitting layers. Furthermore, Patent Document 8 describes a phenomenon in which singlet excitons are generated by the collision and fusion of two triplet excitons (hereinafter sometimes referred to as the triplet-triplet fusion (TTF) phenomenon) in order to improve the performance of organic EL devices. Examples of the performance of organic EL devices include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. [Prior art documents] [Patent documents]
[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2013-157552 [Patent Document 2] International Publication No. 2004 / 018587 [Patent Document 3] International Publication No. 2005 / 115950 [Patent Document 4] International Publication No. 2011 / 077691 [Patent Document 5] Japanese Patent Application Publication No. 2018-125504 [Patent Document 6] US Patent Application Publication No. 2019 / 280209 [Patent Document 7] Japanese Patent Application Laid-Open No. 2007-294261 [Patent Document 8] International Publication No. 2010 / 134350 Summary of the Invention [Problem to be solved by the invention]
[0004] For example, Patent Document 7 describes an organic EL device in which bathophenanthroline (BCP), a phenanthroline compound having a phenanthroline skeleton, is vapor-deposited on an emitting layer to form an electron transport layer, BCP and cesium (Cs) are co-deposited to form an electron injection layer, and aluminum is vapor-deposited to form a cathode. When a phenanthroline compound is used in an intermediate layer disposed between light-emitting units of a tandem organic EL device having a plurality of light-emitting units, the device life tends to be shortened.
[0005] An object of the present invention is to provide an organic electroluminescent element with improved performance. Another object of the present invention is to provide an organic electroluminescent element with improved luminous efficiency and a longer life, and to provide an electronic device equipped with the organic electroluminescent element. [Means for solving the problem]
[0006] According to one aspect of the present invention, there is provided an organic electroluminescence device, an anode; A cathode; two or more light-emitting units disposed between the anode and the cathode; a first cathode-side organic layer disposed between the anode and the cathode; At least one of the two or more light-emitting units is a stacked light-emitting unit; the first cathode-side organic layer is disposed on the cathode side of at least one of the stacked light-emitting units; the first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton, the stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer; the first light-emitting layer contains a first host material; the second light-emitting layer contains a second host material; the first host material and the second host material are different from each other; the first light-emitting layer contains at least a first light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less, the second light-emitting layer contains at least a second light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less, the first luminescent compound and the second luminescent compound are the same or different from each other; The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 3): An organic electroluminescent device is provided. T1(H1)>T1(H2) ... (Number 3)
[0007] According to one aspect of the present invention, there is provided an organic electroluminescence device, an anode; A cathode; two or more light-emitting units disposed between the anode and the cathode; a first cathode-side organic layer disposed between the anode and the cathode; At least one of the two or more light-emitting units is a stacked light-emitting unit; the first cathode-side organic layer is disposed on the cathode side of at least one of the stacked light-emitting units; the first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton, the stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer; the first light-emitting layer contains a first host material; the second light-emitting layer contains a second host material; The first host material has, in a molecule, a structure satisfying the following condition (i) or a structure satisfying the following condition (ii): the second host material is an anthracene derivative, the first host material and the second host material are different from each other; the first light-emitting layer contains at least a first light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less, the second light-emitting layer contains at least a second light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less, the first luminescent compound and the second luminescent compound are the same or different from each other; An organic electroluminescent device is provided. Condition (i) The compound has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further connected by a bridge at at least one portion other than the single bond. Condition (ii) The compound has a linking structure including a benzene ring and a naphthalene ring linked by a single bond, and the benzene ring and the naphthalene ring in the linking structure are each independently further fused with a single ring or a fused ring, or are not fused with a fused ring, and the benzene ring and the naphthalene ring in the linking structure are further linked by a bridge at at least one portion other than the single bond.
[0008] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to the above-described aspect of the present invention.
[0009] According to one embodiment of the present invention, an organic electroluminescence element with improved performance can be provided. Furthermore, according to another embodiment of the present invention, an organic electroluminescence element with improved luminous efficiency and a longer life can be provided. Furthermore, according to another embodiment of the present invention, an electronic device incorporating the organic electroluminescence element can be provided. [Brief explanation of the drawings]
[0010] [Figure 1] 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION
[0011] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.
[0012] In this specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.
[0013] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, 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. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. Furthermore, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.
[0014] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.
[0015] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0016] In this specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY atoms" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.
[0017] In this specification, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. In this specification, "substituted" in the context of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the context of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.
[0018] "Substituents described herein" The substituents described in this specification will be explained below.
[0019] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. Unless otherwise specified in this specification, the "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. Unless otherwise specified, the "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
[0020] "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent, and examples of the substituted aryl group in the specific example group G1A below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.
[0021] Unsubstituted aryl groups (specific example group G1A): 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, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl groups, 9,9'-spirobifluorenyl group, benzofluorenyl groups, dibenzofluorenyl groups, fluoranthenyl group, benzofluoranthenyl group, perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).
[0022] [ka]
[0023] [ka]
[0024] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl groups, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.
[0025] "Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which a hydrogen atom of the "unsubstituted heterocyclic group" in the specific example group G2A below is replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are also included. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent.
[0026] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).
[0027] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).
[0028] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, a triazolyl group, tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, a triazinyl group, Indolyl groups, isoindolyl groups, an indolizinyl group, a quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, a quinazolinyl group, quinoxalinyl group, benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, acridinyl group, phenazinyl group, a carbazolyl group, a benzocarbazolyl group, morpholino group, phenoxazinyl group, a phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.
[0029] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and Diazanaphthobenzofuranyl group.
[0030] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
[0031] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):
[0032] [ka]
[0033] [ka]
[0034] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.
[0035] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and Biphenylylquinazolinyl group.
[0036] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].
[0037] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].
[0038] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):
[0039] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y A or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.
[0040] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when simply referring to an "alkyl group," both an "unsubstituted alkyl group" and a "substituted alkyl group" are included. The term "substituted alkyl group" refers to an "unsubstituted alkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Note that the examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent.
[0041] Unsubstituted alkyl groups (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
[0042] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.
[0043] "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to an "unsubstituted alkenyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of the alkenyl group itself has been further replaced with a substituent, and groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of a substituent has been further replaced with a substituent.
[0044] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group, and 3-butenyl group.
[0045] Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
[0046] "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.
[0047] Unsubstituted alkynyl groups (specific example group G5A): ethynyl groups.
[0048] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to an "unsubstituted cycloalkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" of specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself have been replaced with a substituent, and a group in the "substituted cycloalkyl group" of specific example group G6B in which a hydrogen atom of a substituent has been further replaced with a substituent.
[0049] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
[0050] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.
[0051] -Si(R 901 )(R 902 )(R 903 ) a group represented by -Si(R 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -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) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) may be the same as or different from each other.
[0052] -O-(R 904 ) a group represented by -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
[0053] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
[0054] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.
[0055] "Halogen atoms" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0056] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The term "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with a fluorine atom.
[0057] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. The term "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include the examples of the above-mentioned "alkyl groups" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.
[0058] "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.
[0059] "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.
[0060] "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0061] "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.
[0062] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.
[0063] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.
[0064] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.
[0065] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.
[0066] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.
[0067] [ka]
[0068] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:
[0069] [ka]
[0070] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
[0071] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.
[0072] [ka]
[0073] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.
[0074] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.
[0075] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.
[0076] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.
[0077] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group." Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.
[0078] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).
[0079] [ka]
[0080] [ka]
[0081] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
[0082] [ka]
[0083] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.
[0084] [ka]
[0085] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.
[0086] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).
[0087] [ka]
[0088] [ka]
[0089] [ka]
[0090] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.
[0091] [ka]
[0092] [ka]
[0093] [ka]
[0094] [ka]
[0095] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.
[0096] The above is the explanation of "substituents described in this specification."
[0097] - "When bonded to form a ring" In this specification, the phrase "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle, bond with each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle", the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring", or the case where "one or more pairs of adjacent groups do not bond with each other". In this specification, the cases where "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they bond to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be explained as an example.
[0098] [ka]
[0099] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.
[0100] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A At the same time, R 925 and R 926 and are bonded to each other to form ring Q B When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).
[0101] [ka]
[0102] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.
[0103] [ka]
[0104] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.
[0105] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R 921 and R 922 and Q are bonded together to form a ring A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by
[0106] Here, unless otherwise specified in this specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of carbon or nitrogen), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more groups" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more groups combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.
[0107] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").
[0108] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, 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(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and a group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms, where R 901 ~R 907 are each independently, hydrogen atoms, 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, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R 903 If there are two or more, there are two or more R903 are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.
[0109] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and The group is selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.
[0110] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; an aryl group having 6 to 18 ring carbon atoms, and The group is selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.
[0111] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."
[0112] Unless otherwise specified in this specification, any adjacent substituents may be bonded to each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.
[0113] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.
[0114] First Embodiment (organic electroluminescence element) The organic electroluminescence element according to this embodiment has the following basic configuration.
[0115] (Basic configuration) The organic electroluminescent device according to this embodiment includes an anode, a cathode, two or more light-emitting units disposed between the anode and the cathode, and a first cathode-side organic layer disposed between the anode and the cathode, wherein at least one of the two or more light-emitting units is a stacked light-emitting unit, the first cathode-side organic layer is disposed on the cathode side of at least one of the stacked light-emitting units, the first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton, and the stacked light-emitting units The light-emitting device includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer contains a first host material, and the second light-emitting layer contains a second host material, the first host material and the second host material being different from each other, the first light-emitting layer contains at least a first light-emitting compound that exhibits emission with a maximum peak wavelength of 500 nm or less, and the second light-emitting layer contains at least a second light-emitting compound that exhibits emission with a maximum peak wavelength of 500 nm or less, and the first light-emitting compound and the second light-emitting compound are the same as or different from each other.
[0116] In addition to the basic configuration described above, the organic EL device according to this embodiment further includes at least one of the following elements (Element 1) and (Element 2).
[0117] (Element 1) In element 1, the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 3). T1(H1)>T1(H2) ... (Number 3)
[0118] (Element 2) In Element 2, the first host material has a structure that satisfies the following condition (i) or the following condition (ii) in a molecule, the first benzene ring and the second benzene ring in the biphenyl structure are further linked by a bridge at at least one moiety other than the single bond, and the second host material is an anthracene derivative: Condition (i) The compound has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further connected by a bridge at at least one portion other than the single bond. Condition (ii) The compound has a linking structure including a benzene ring and a naphthalene ring linked by a single bond, and the benzene ring and the naphthalene ring in the linking structure are each independently further fused with a single ring or a fused ring, or are not fused with a fused ring, and the benzene ring and the naphthalene ring in the linking structure are further linked by a bridge at at least one portion other than the single bond.
[0119] Hereinafter, an organic EL element according to this embodiment including the above-described basic configuration and at least one of (element 1) and (element 2) will be described.
[0120] In this specification, an organic electroluminescent element having two or more light-emitting units disposed between an anode and a cathode is referred to as a tandem organic electroluminescent element (tandem organic EL element).
[0121] According to this embodiment, it is possible to provide an organic electroluminescence element with improved luminous efficiency. Triplet-triplet-annhilation (sometimes referred to as TTA) has been known as a technique for improving the luminous efficiency of organic electroluminescence devices. TTA is a mechanism in which triplet excitons collide with each other to generate singlet excitons. The TTA mechanism is also sometimes referred to as the TTF mechanism, as described in Patent Document 8.
[0122] The TTF phenomenon will be explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As has been conventionally known, the spin state of these excitons is 25% singlet excitons and 75% triplet excitons. In conventional fluorescent elements, 25% of the singlet excitons emit light when they relax to the ground state, but the remaining 75% of the triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent elements was said to be 25%. On the other hand, the behavior of triplet excitons generated inside organic materials has been theoretically investigated. According to S.M. Bachilo et al. (J.Phys.Chem.A,104,7711(2000)), assuming that higher-order excitons such as quintets immediately return to triplets, triplet excitons (hereinafter referred to as triplet excitons) 3 A * When the density of triplet excitons (hereinafter referred to as triplet excitons) increases, triplet excitons collide with each other, causing the reaction shown in the following formula: 1 A represents the ground state, 1 A * represents the lowest excited singlet exciton. 3 A * + 3 A * →(4 / 9) 1 A+(1 / 9) 1 A * +(13 / 9) 3 A * That is, 5 3 A * →4 1 A+1A *It is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will convert to singlet excitons. Therefore, the singlet excitons contributing to light are 40%, calculated by adding 75% × (1 / 5) = 15% to the initially generated 25%. In this case, the TTF ratio (TTF ratio) of the total luminescence intensity is 15 / 40, or 37.5%. Furthermore, if we assume that singlet excitons are generated by collisions between the initially generated 75% triplet excitons (i.e., one singlet exciton is generated from two triplet excitons), then an extremely high internal quantum efficiency of 62.5% is obtained by adding 75% × (1 / 2) = 37.5% to the initially generated 25% singlet excitons. In this case, the TTF ratio is 37.5 / 62.5 = 60%.
[0123] In the organic electroluminescent device according to this embodiment, triplet excitons generated by recombination of holes and electrons in the first light-emitting layer in the stacked light-emitting unit are thought to be less likely to be quenched at the interface between the first light-emitting layer and the organic layer, even if excess carriers are present at the interface between the first light-emitting layer and the organic layer that is in direct contact with the first light-emitting layer. For example, when the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching by excess electrons is thought to occur. On the other hand, when the recombination region is locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching by excess holes is thought to occur. The organic electroluminescent device according to this embodiment comprises a stacked light-emitting unit including at least two light-emitting layers (i.e., a first light-emitting layer and a second light-emitting layer) that satisfy a predetermined relationship, and the triplet energy T1(H1) of the first host material in the first light-emitting layer and the triplet energy T1(H2) of the second host material in the second light-emitting layer satisfy the relationship of the above-described mathematical formula (Mathematical Formula 3). By providing a stacked light-emitting unit including a first light-emitting layer and a second light-emitting layer so as to satisfy the relationship of the above mathematical formula (3), triplet excitons generated in the first light-emitting layer can migrate to the second light-emitting layer without being quenched by excess carriers, and reverse migration from the second light-emitting layer to the first light-emitting layer can be suppressed. As a result, the TTF mechanism is exerted in the second light-emitting layer, and singlet excitons are efficiently generated, improving the luminous efficiency. In this way, the stacked light-emitting unit in the organic electroluminescence device comprises, as distinct regions, a first light-emitting layer that mainly generates triplet excitons and a second light-emitting layer that mainly exhibits the TTF mechanism by utilizing triplet excitons transferred from the first light-emitting layer, and a compound having a smaller triplet energy than the first host material in the first light-emitting layer is used as the second host material in the second light-emitting layer, thereby creating a difference in triplet energy and improving the luminous efficiency.
[0124] Phenanthroline compounds having a phenanthroline skeleton are suitable for use as electron transport materials in so-called tandem organic EL devices having multiple light-emitting units because they easily generate electric charges. However, the phenanthroline compounds have low resistance to holes, and when holes move from the light-emitting layer to an organic layer (e.g., an electron transport layer) containing the phenanthroline compound, the phenanthroline compound tends to deteriorate, resulting in a shortened device life. In the organic EL device according to this embodiment, a first cathode-side organic layer containing a phenanthroline compound is disposed on the cathode side of a stacked light-emitting unit including a first light-emitting layer and a second light-emitting layer. This stacked light-emitting unit includes, as distinct regions, a first light-emitting layer that primarily generates triplet excitons and a second light-emitting layer that primarily exhibits the TTF mechanism by utilizing triplet excitons transferred from the first light-emitting layer. This allows the first cathode-side organic layer containing the phenanthroline compound, which is prone to degradation, to be spaced apart from the first light-emitting layer (recombination layer), thereby suppressing the number of holes that transfer from the stacked light-emitting unit to the first cathode-side organic layer, and thus prolonging the life of the organic EL device.
[0125] The first cathode-side organic layer is an organic layer disposed on the cathode side of at least one stacked light-emitting unit, and may be referred to as an intermediate layer.
[0126] The intermediate layer is also generally called an intermediate electrode, intermediate conductive layer, charge generating layer, electron withdrawing layer, connecting layer, connector layer, or intermediate insulating layer. The intermediate layer is a layer that supplies electrons to a layer disposed closer to the anode than the intermediate layer and supplies holes to a layer disposed closer to the cathode than the intermediate layer. The intermediate layer can be formed from a known material. The intermediate layer may consist of one layer or two or more layers. A unit consisting of two or more intermediate layers may be referred to as an intermediate unit. The compositions of the multiple intermediate layers contained in the intermediate unit may be the same or different.
[0127] Furthermore, a plurality of layers including an emitting layer disposed between an intermediate layer or intermediate unit and an anode or cathode may be referred to as an emitting unit. Examples of the device configuration of an organic EL device having a plurality of emitting units include the following device configurations (TND1) to (TND4). (TND1) Anode / First light-emitting unit / Intermediate layer / Second light-emitting unit / Cathode (TND2) Anode / First light-emitting unit / Intermediate unit / Second light-emitting unit / Cathode (TND3) Anode / First light-emitting unit / First intermediate layer / Second light-emitting unit / Second intermediate layer / Third light-emitting unit / Cathode (TND4) Anode / First light-emitting unit / First intermediate unit / Second light-emitting unit / Second intermediate unit / Third light-emitting unit / Cathode In the organic EL device of this embodiment, the number of light-emitting units and intermediate layers (or intermediate units) is not limited to the examples (TND1) to (TND4) shown here.
[0128] In the device configurations (TND1) to (TND4) above, it is also preferable that the first cathode-side organic layer is included as at least one of the intermediate layers, or included as an intermediate layer in at least one of the intermediate units.
[0129] The first light-emitting layer and the second light-emitting layer are preferably included in at least one of the first light-emitting unit, the second light-emitting unit, and the third light-emitting unit. It is also preferable that the first light-emitting layer and the second light-emitting layer are included in all light-emitting units of the organic EL device.
[0130] In the element configurations (TND1) to (TND4) above, it is preferable that the light-emitting unit disposed on the anode side of the intermediate layer as the first cathode-side organic layer or the light-emitting unit disposed on the anode side of the intermediate unit including the first cathode-side organic layer is a stacked light-emitting unit according to this embodiment.
[0131] The stacked light-emitting unit of the organic EL device according to this embodiment may include one or more organic layers in addition to the first and second light-emitting layers, such as at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.
[0132] In the organic EL device according to this embodiment, the organic layer of the stacked light-emitting unit may be composed of only the first light-emitting layer and the second light-emitting layer, or may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, and the like.
[0133] The region disposed on the anode side of the light-emitting layer in the light-emitting unit is sometimes referred to as a hole-transporting region. The hole-transporting region may be a single layer or multiple layers. In addition to the hole-transporting layer, examples of layers constituting the hole-transporting region include a hole-injecting layer and an electron-blocking layer.
[0134] The region disposed on the cathode side of the light-emitting layer of the light-emitting unit is sometimes referred to as an electron transport region. The electron transport region may be a single layer or multiple layers. In addition to the electron transport layer, examples of layers constituting the electron transport region include an electron injection layer and a hole blocking layer.
[0135] The organic EL device according to this embodiment may include an emitting unit having at least one emitting layer as an emitting unit other than the stacked emitting unit, and the emitting unit other than the stacked emitting unit may include, as an organic layer other than the emitting layer, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.
[0136] In the organic EL device according to this embodiment, the two or more light-emitting units preferably include a stacked light-emitting unit and at least one phosphorescent light-emitting unit different from the stacked light-emitting unit. The phosphorescent light-emitting unit preferably contains a phosphorescent compound that exhibits phosphorescence. The phosphorescent compound is preferably a metal complex. The metal complex as the phosphorescent compound is preferably an iridium complex, a copper complex, a platinum complex, an osmium complex, or a gold complex. The phosphorescent-emitting unit preferably has at least one phosphorescent-emitting layer containing a phosphorescent compound. The phosphorescent-emitting unit may have two or more phosphorescent-emitting layers. When the phosphorescent-emitting unit has two or more phosphorescent-emitting layers, the phosphorescent-emitting layers may or may not be in direct contact with each other. The phosphorescent-emitting unit preferably includes a green phosphorescent-emitting layer containing a green-emitting phosphorescent compound and a red phosphorescent-emitting layer containing a red-emitting phosphorescent compound. In this specification, green emission refers to emission having a maximum peak wavelength in the emission spectrum ranging from 500 nm to 550 nm. In this specification, red emission refers to emission having a maximum peak wavelength in the emission spectrum ranging from 600 nm to 640 nm. When the organic EL element according to this embodiment has a phosphorescent light-emitting unit, it preferably has two or more stacked light-emitting units. It is also preferable that the organic EL element according to this embodiment has one stacked light-emitting unit and one phosphorescent light-emitting unit.
[0137] It is also preferable that the organic EL device according to this embodiment does not include a phosphorescent unit.
[0138] 1 shows a schematic configuration of an organic EL element 1 as an example of an organic EL element according to this embodiment. The organic EL element 1 is a tandem organic EL element. The organic EL element 1 includes a substrate 2, a cathode 4, an anode 3, an intermediate unit 20 between the cathode 4 and the anode 3, a first light-emitting unit 11 between the intermediate unit 20 and the anode 3, and a second light-emitting unit 12 between the intermediate unit 20 and the cathode 4. In the organic EL device 1, the first light-emitting unit 11 and the second light-emitting unit 12 are connected in series via the intermediate unit 20. The organic EL element 1 includes two light-emitting units: a first light-emitting unit 11 and a second light-emitting unit 12. The first light-emitting unit 11 and the second light-emitting unit 12 in the organic EL element 1 are both stacked light-emitting units according to this embodiment. The first light-emitting unit 11 may be referred to as a first stacked light-emitting unit. The second light-emitting unit 12 may be referred to as a second stacked light-emitting unit.
[0139] The first light-emitting unit 11 is configured by laminating a hole injection layer 113, a hole transport layer 114, a first light-emitting layer 111, a second light-emitting layer 112, and an electron transport layer 115 in this order from the anode 3 side.
[0140] The second light-emitting unit 12 is configured by laminating a hole transport layer 123, a first light-emitting layer 121, a second light-emitting layer 122, an electron transport layer 124, and an electron injection layer 125 in this order from the anode 3 side.
[0141] The intermediate unit 20 is configured by laminating, in this order from the anode 3 side, a first cathode-side organic layer 21 (sometimes referred to as a first N layer) and a first P layer 22.
[0142] The present invention is not limited to the configuration of the organic EL element shown in Fig. 1. Examples of organic EL elements with different configurations include an embodiment in which, in the light-emitting unit, a second light-emitting layer and a first light-emitting layer are laminated in this order from the anode side. The numbers of light-emitting units and intermediate units are also not limited to the configuration of the organic EL element shown in Fig. 1. Other examples include an embodiment in which, instead of an intermediate unit, a first cathode-side organic layer is disposed between the first light-emitting unit and the second light-emitting unit as an intermediate layer.
[0143] The organic EL element according to this embodiment may be a bottom-emission type organic EL element, or may be a top-emission type organic EL element.
[0144] Furthermore, examples of the device configuration of an organic EL device having a stacked light-emitting unit and a phosphorescent light-emitting unit as the plurality of light-emitting units include the following device configurations (TND5) to (TND8). (TND5) Anode / First light-emitting unit (stacked light-emitting unit) / Intermediate layer / Second light-emitting unit (phosphorescent light-emitting unit) / Cathode (TND6) Anode / First light-emitting unit (stacked light-emitting unit) / Middle unit / Second light-emitting unit (phosphorescent light-emitting unit) / Cathode (TND7) Anode / First light-emitting unit (stacked light-emitting unit) / First intermediate layer / Second light-emitting unit (phosphorescent light-emitting unit) / Second intermediate layer / Third light-emitting unit (stacked light-emitting unit) / Cathode (TND8) Anode / First light-emitting unit (stacked light-emitting unit) / First intermediate unit / Second light-emitting unit (phosphorescent light-emitting unit) / Second intermediate unit / Third light-emitting unit (stacked light-emitting unit) / Cathode The number of light-emitting units and intermediate layers (or intermediate units) is not limited to the examples shown in (TND5) to (TND8), and the arrangement order of the stacked light-emitting units and phosphorescent light-emitting units is not limited to the examples shown in (TND5) to (TND8).
[0145] (First cathode-side organic layer) The first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton.
[0146] The first cathode-side organic layer preferably contains a phenanthroline compound and an electron-donating material. The electron donor material is preferably at least one selected from the group consisting of electron donating metals, metal compounds, and metal complexes. Specifically, the electron donor material is preferably at least one selected from the group consisting of alkali metals, alkali metal compounds, organometallic complexes containing alkali metals, alkaline earth metals, alkaline earth metal compounds, organometallic complexes containing alkaline earth metals, rare earth metals, rare earth metal compounds, and organometallic complexes containing rare earth metals. Among these, at least one selected from the group consisting of alkali metals, alkaline earth metals, and rare earth metals, compounds of rare earth metals, and complexes of rare earth metals is more preferred. For example, the first cathode-side organic layer preferably contains a phenanthroline compound and at least one metal selected from the group consisting of Li, Yb, and Cs.
[0147] (Intermediate unit) The organic EL device according to this embodiment may include an intermediate unit between the light-emitting units. The intermediate unit includes a plurality of organic layers. The first cathode-side organic layer may be an organic layer constituting the intermediate unit. In the organic EL device according to this embodiment, it is also preferable that an intermediate unit is disposed on the cathode side of at least one of the stacked light-emitting units, and that the intermediate unit includes a first cathode-side organic layer. The intermediate unit preferably includes at least one N layer and at least one P layer. The N layer is disposed closer to the anode than the P layer. In the organic EL device according to this embodiment, the intermediate unit preferably includes a first cathode-side organic layer as the N layer. The intermediate unit may have, as the multiple N layers, a first N layer disposed closer to the anode and a second N layer disposed closer to the cathode than the first N layer. The first cathode-side organic layer may be either the first N layer or the second N layer. If the second N layer is the first cathode-side organic layer, it is easy to separate the first cathode-side organic layer and the first light-emitting layer. The N layer preferably contains a π-electron deficient compound and an electron donating material. Examples of the π-electron deficient compound include compounds capable of coordinating with metal atoms. Examples of the π-electron deficient compound include phenanthroline compounds, benzimidazole compounds, azine compounds, and quinolinol. The P layer is a layer containing an acceptor material. The P layer may be a layer doped with an acceptor material (P-doped layer). The acceptor material may be appropriately selected from the "substances with high hole injection properties" exemplified in the section on the hole injection layer.
[0148] In the organic EL element according to this embodiment, a second cathode-side organic layer may be disposed between the first light-emitting layer and the first cathode-side organic layer. For example, the organic EL element according to this embodiment may have, from the anode side, a second light-emitting layer, a first light-emitting layer, a second cathode-side organic layer, and a first cathode-side organic layer in this order. In this manner, when the second light-emitting layer and the first light-emitting layer are arranged in this order from the anode side, the second cathode-side organic layer can separate the first light-emitting layer and the first cathode-side organic layer. Furthermore, for example, the organic EL device according to this embodiment may have, from the anode side, a first light-emitting layer, a second light-emitting layer, a second cathode-side organic layer, and a first cathode-side organic layer in this order. Note that when the first light-emitting layer and the second light-emitting layer are provided in this order from the anode side, the first light-emitting layer and the first cathode-side organic layer containing a phenanthroline compound can be spaced apart even if the second cathode-side organic layer is not provided.
[0149] In the organic EL device according to this embodiment, the second cathode-side organic layer preferably does not contain a phenanthroline compound having a phenanthroline skeleton.
[0150] The second cathode-side organic layer may be an N layer different from the first cathode-side organic layer in the intermediate unit. For example, the second cathode-side organic layer may be the first N layer, and the first cathode-side organic layer may be the second N layer. The second cathode-side organic layer may also be an electron transport layer or a hole blocking layer in the light-emitting unit.
[0151] In the organic EL element according to this embodiment, the first light-emitting layer and the first cathode-side organic layer are preferably spaced apart by 30 nm or more. This is thought to facilitate suppressing the amount of holes that move from the stacked light-emitting unit to the first cathode-side organic layer, thereby making it easier to extend the life of the organic EL element.
[0152] In the organic EL device according to this embodiment, at least one light-emitting unit may be disposed between the first cathode-side organic layer and the cathode. In the organic EL device according to this embodiment, the first cathode-side organic layer containing a phenanthroline compound may be disposed between the stacked light-emitting unit and another light-emitting unit different from the stacked light-emitting unit.
[0153] When the organic layer containing the phenanthroline compound is disposed at a position where it is easily subject to electron injection from the cathode (for example, when it is in direct contact with the cathode or the electron injection layer), the organic layer containing the phenanthroline compound is easily subject to electron injection, and therefore deterioration due to injection of holes transferred from the light-emitting layer is alleviated. On the other hand, when an organic layer containing a phenanthroline compound is disposed between light-emitting units and is not activated by the cathode (metal electrode) and is therefore less susceptible to electron injection, the phenanthroline compound is easily degraded by holes. In the organic EL element according to this embodiment, even if the first cathode-side organic layer containing a phenanthroline compound is disposed between the light-emitting units and is therefore less susceptible to electron injection, the stacked light-emitting units are disposed on the anode side of the first cathode-side organic layer, which is thought to suppress the amount of holes moving from the stacked light-emitting units to the first cathode-side organic layer and thereby extend the life of the organic EL element.
[0154] In the organic EL device according to this embodiment, the organic layer containing the phenanthroline compound may or may not be located closer to the cathode than the light-emitting unit that is located closest to the cathode among the two or more light-emitting units.
[0155] (Light-emitting unit) The organic EL device according to this embodiment includes two or more light-emitting units. Each light-emitting unit includes an emitting layer. The organic EL device according to this embodiment includes at least one stacked light-emitting unit, and the stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer, as described above. The organic EL device according to this embodiment may include two or more stacked light-emitting units. The light-emitting units other than the stacked light-emitting units may include a single light-emitting layer or multiple light-emitting layers.
[0156] In the organic EL device according to this embodiment, it is also preferable that the second light-emitting layer of the stacked light-emitting unit is disposed between the first light-emitting layer and the first cathode-side organic layer. Since the second light-emitting layer is disposed between the first light-emitting layer serving as a recombination layer and the first cathode-side organic layer containing a phenanthroline compound, the first light-emitting layer and the first cathode-side organic layer can be separated by the second light-emitting layer even when no other organic layer is disposed between the first light-emitting layer and the first cathode-side organic layer.
[0157] In the organic EL device according to this embodiment, it is also preferable that the first light-emitting layer of the stacked light-emitting unit is disposed between the second light-emitting layer and the first cathode-side organic layer.
[0158] The organic EL device according to this embodiment may have a first light-emitting layer and a second light-emitting layer in this order from the anode side, or may have a second light-emitting layer and a first light-emitting layer in this order from the anode side. Regardless of the order of the first light-emitting layer and the second light-emitting layer, by selecting a combination of materials that satisfies the relationship of the above mathematical formula (Mathematical Formula 3), the effect of the stacked light-emitting layer can be expected.
[0159] In the organic EL device according to this embodiment, when the first and second light-emitting layers are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is also preferable that the hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material satisfy the relationship shown in the following formula (31). When the first host material and the second host material satisfy the relationship shown in the following formula (31), the deterioration of the phenanthroline compound can be further suppressed. μh(H1)>μh(H2) …(Equation 31)
[0160] In the organic EL device according to this embodiment, when the first and second light-emitting layers are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is also preferable that the hole mobility μh(H1) of the first host material, the electron mobility μe(H1) of the first host material, the hole mobility μh(H2) of the second host material, and the electron mobility μe(H2) of the second host material satisfy the relationship shown in the following formula (32). When the first host material and the second host material satisfy the relationship shown in the following formula (32), deterioration of the phenanthroline compound can be further suppressed. (μe(H1) / μh(H1))<(μe(H2) / μh(H2)) …(Math. 32)
[0161] In the organic EL element according to this embodiment, when the first and second light-emitting layers are stacked in the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is also preferable that the electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the relationship of the following formula (33): When the first host material and the second host material satisfy the relationship of the following formula (33), the recombination ability of holes and electrons in the first light-emitting layer is improved. μe(H1)<μe(H2) …(Equation 33)
[0162] The electron mobility can be measured by measuring impedance using a mobility evaluation element fabricated by the following procedure. The mobility evaluation element is fabricated, for example, by the following procedure. A compound (Target) whose electron mobility is to be measured is vapor-deposited on a glass substrate with an aluminum electrode (anode) so as to cover the aluminum electrode, thereby forming a measurement target layer. An electron transport layer is formed on this measurement target layer by vapor-depositing the following compound ET-A. An electron injection layer is formed on this electron transport layer by vapor-depositing LiF. A metal cathode is formed on this electron injection layer by vapor-depositing metallic aluminum (Al). The above-mentioned configuration of the device for evaluating mobility can be shown in simplified form as follows. glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / Al(50) The numbers in parentheses indicate the film thickness (nm).
[0163] [ka]
[0164] The element for evaluating electron mobility is placed in an impedance measurement device and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship in the following calculation formula (C1). Calculation formula (C1): M=jωZ In the above formula (C1), j is an imaginary unit whose square is -1, and ω is the angular frequency [rad / s]. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the following calculation formula (C2). Calculation formula (C2): τ=1 / (2πfmax) In the above formula (C2), π is the symbol representing the ratio of the circumference of a circle to its diameter. Using the above τ, the electron mobility μe is calculated from the relationship of the following calculation formula (C3-1). Calculation formula (C3-1):μe=d 2 / (Vτ) In the above formula (C3-1), d is the total film thickness of the organic thin films that make up the device, and in the case of the device configuration for evaluating the electron mobility, d=210 [nm].
[0165] The hole mobility can be measured by measuring impedance using a mobility evaluation device fabricated by the following procedure. The mobility evaluation device is fabricated, for example, by the following procedure. On a glass substrate with an ITO transparent electrode (anode), the following compound HA-2 is vapor-deposited so as to cover the transparent electrode to form a hole injection layer. On top of this hole injection layer, the following compound HT-A is vapor-deposited to form a hole transport layer. Subsequently, a compound Target, whose hole mobility is to be measured, is vapor-deposited to form a measurement target layer. On top of this measurement target layer, metallic aluminum (Al) is vapor-deposited to form a metal cathode. The above-mentioned configuration of the device for evaluating mobility can be shown in simplified form as follows. ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80) The numbers in parentheses indicate the film thickness (nm).
[0166] [ka]
[0167] The hole mobility evaluation device is placed in an impedance measurement device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At this time, a DC voltage V is applied to the device simultaneously with an AC amplitude of 0.1 V. The modulus M is calculated from the measured impedance Z using the relationship in the above calculation formula (C1). In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax showing the peak using the above calculation formula (C2). Using τ obtained from the above formula (C2), the hole mobility μh is calculated from the relationship of the following formula (C3-2). Calculation formula (C3-2):μh=d 2 / (Vτ) In the above formula (C3-2), d is the total film thickness of the organic thin films that make up the device, and in the case of the device configuration for evaluating hole mobility, d=215 [nm].
[0168] The electron and hole mobilities herein are expressed as the square root of the electric field strength, E 1 / 2 =500[V 1 / 2 / cm1 / 2 The square root of the electric field strength E 1 / 2 can be calculated from the relationship of the following calculation formula (C4). Calculation formula (C4): E 1 / 2 =V 1 / 2 / d 1 / 2 The impedance measurement is performed using a Solartron 1260 model impedance measuring device, and for higher accuracy, a Solartron 1296 model dielectric constant measurement interface can also be used.
[0169] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 5). T1(H1)-T1(H2)>0.03 eV … (Equation 5)
[0170] (First light-emitting layer) The first light-emitting layer contains a first host material, which is a compound different from the second host material contained in the second light-emitting layer. The first light-emitting layer contains at least a first light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less. The first light-emitting compound is preferably a fluorescent compound that emits fluorescent light having a maximum peak wavelength of 500 nm or less.
[0171] In the organic EL device according to this embodiment, the first light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.
[0172] In the organic EL device according to this embodiment, the first light-emitting compound is preferably not a boron-containing complex, and more preferably not a complex.
[0173] In the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a metal complex. Also, in the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a boron-containing complex.
[0174] In the organic EL device according to this embodiment, the first light-emitting layer preferably does not contain a phosphorescent material (dopant material). The first light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex, such as an iridium complex, an osmium complex, or a platinum complex.
[0175] In the emission spectrum of the first light-emitting compound, the peak at which the emission intensity is greatest is defined as the maximum peak, and when the height of the maximum peak is defined as 1, the heights of other peaks appearing in the emission spectrum are preferably less than 0.6. Note that the peaks in the emission spectrum are defined as local maxima. In addition, it is preferable that the number of peaks in the emission spectrum of the first luminescent compound is less than three.
[0176] In the organic EL device according to this embodiment, the first light-emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the device is in operation. The maximum peak wavelength of the light emitted from the light-emitting layer when the device is operating can be measured by the following method.
[0177] The maximum peak wavelength λp of the light emitted from the light-emitting layer when the device is operating The maximum peak wavelength λp1 of the light emitted from the first light-emitting layer when the device is driven is determined by the following equation: 2 The spectral radiance spectrum when a voltage is applied to the element so that: is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the maximum peak wavelength λp1 (unit: nm) is calculated. The maximum peak wavelength λp2 of the light emitted from the second light-emitting layer when the device is driven is determined by the following equation: 2The spectral radiance spectrum when a voltage is applied to the element so that: is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the maximum peak wavelength λp2 (unit: nm) is calculated.
[0178] In the organic EL device according to this embodiment, it is preferable that the singlet energy S1(H1) of the first host material and the singlet energy S1(D1) of the first light-emitting compound satisfy the relationship shown in the following formula (Mathematical Formula 20). S1(H1)>S1(D1) ... (Number 20) The singlet energy S1 means the energy difference between the lowest excited singlet state and the ground state.
[0179] When the first host material and the first light-emitting compound satisfy the relationship of mathematical formula (Mathematical Formula 20), singlet excitons generated on the first host material can easily transfer energy from the first host material to the first light-emitting compound, contributing to the fluorescent emission of the first light-emitting compound.
[0180] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first light-emitting compound satisfy the relationship shown in the following formula (Mathematical Formula 20A). T1(D1)>T1(H1) ... (Math 20A)
[0181] When the first host material and the first light-emitting compound satisfy the relationship of mathematical formula (Mathematical Formula 20A), triplet excitons generated in the first light-emitting layer move over the first host material rather than the first light-emitting compound, which has a higher triplet energy, and therefore are more likely to move to the second light-emitting layer.
[0182] The organic EL element according to this embodiment preferably satisfies the relationship of the following mathematical formula (Mathematical Formula 20B). T1(D1)>T1(H1)>T1(H2) ... (Math 20B)
[0183] In the organic EL device according to this embodiment, the first light-emitting compound is preferably contained in the first light-emitting layer in an amount exceeding 1.1% by mass, i.e., the first light-emitting layer preferably contains the first light-emitting compound in an amount exceeding 1.1% by mass of the total mass of the first light-emitting layer, more preferably 1.2% by mass or more of the total mass of the first light-emitting layer, and even more preferably 1.5% by mass or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first light-emitting compound in an amount of 10 mass % or less of the total mass of the first light-emitting layer, more preferably 7 mass % or less of the total mass of the first light-emitting layer, and even more preferably 5 mass % or less of the total mass of the first light-emitting layer.
[0184] In the organic EL device according to this embodiment, the first emitting layer preferably contains the first compound as a first host material in an amount of 60 mass % or more of the total mass of the first emitting layer, more preferably 70 mass % or more of the total mass of the first emitting layer, even more preferably 80 mass % or more of the total mass of the first emitting layer, still more preferably 90 mass % or more of the total mass of the first emitting layer, and even more preferably 95 mass % or more of the total mass of the first emitting layer. The first emitting layer preferably contains the first host material in an amount of 99% by mass or less of the total mass of the first emitting layer. However, when the first light-emitting layer contains a first host material and a first light-emitting compound, the upper limit of the total content of the first host material and the first light-emitting compound is 100% by mass.
[0185] In this embodiment, the first light-emitting layer may contain a material other than the first host material and the first light-emitting compound. The first light-emitting layer may contain only one type of first host material or two or more types of first light-emitting compounds.
[0186] In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is preferably 3 nm or more, more preferably 5 nm or more, which is sufficient to cause recombination of holes and electrons in the first light-emitting layer. In the organic EL device according to this embodiment, the thickness of the first emitting layer is preferably 15 nm or less, more preferably 10 nm or less, which is thin enough to allow triplet excitons to migrate to the second emitting layer. In the organic EL device according to this embodiment, the thickness of the first light-emitting layer is more preferably 3 nm or more and 15 nm or less.
[0187] (Second light-emitting layer) The second light-emitting layer contains a second host material, which is a compound different from the first host material contained in the first light-emitting layer. The second light-emitting layer contains at least a second light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less. The second light-emitting compound is preferably a fluorescent compound that emits fluorescent light having a maximum peak wavelength of 500 nm or less. The method for measuring the maximum peak wavelength of the compound is as described above.
[0188] In the organic EL device according to this embodiment, the second light-emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the device is in operation.
[0189] In the organic EL device according to this embodiment, the half width of the maximum peak of the second light-emitting compound is preferably 1 nm or more and 20 nm or less.
[0190] In the organic EL device according to this embodiment, the Stokes shift of the second light-emitting compound is preferably more than 7 nm. If the Stokes shift of the second luminescent compound exceeds 7 nm, it becomes easier to prevent a decrease in luminous efficiency due to self-absorption. Self-absorption is a phenomenon in which emitted light is absorbed by the same compound, resulting in a decrease in luminous efficiency. Self-absorption is most pronounced in compounds with a small Stokes shift (i.e., a large overlap between the absorption spectrum and the fluorescence spectrum). Therefore, to suppress self-absorption, it is preferable to use a compound with a large Stokes shift (a small overlap between the absorption spectrum and the fluorescence spectrum). The Stokes shift can be measured using the following method. The compound to be measured is 2.0 x 10 -5 The compound is dissolved in toluene at a concentration of 1000 mol / L to prepare a measurement sample. The measurement sample is placed in a quartz cell and irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the absorption spectrum, for example, the Hitachi High-Tech Science U-3900 / 3900H spectrophotometer. The compound to be measured is dissolved in toluene at a concentration of 4.9 x 10 -6 The sample was dissolved in toluene at a concentration of 100 mol / L to prepare a measurement sample. The measurement sample was placed in a quartz cell and irradiated with excitation light at room temperature (300 K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) was measured. A spectrophotometer, such as the F-7000 spectrofluorometer manufactured by Hitachi High-Tech Science Corporation, can be used to measure the fluorescence spectrum. From these absorption and fluorescence spectra, the difference between the maximum absorption wavelength and the maximum fluorescence wavelength is calculated to determine the Stokes shift (SS), which is expressed in nm.
[0191] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(D2) of the second light-emitting compound and the triplet energy T1(H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 3A). T1(D2)>T1(H2) ... (Math 3A)
[0192] In the organic EL device according to this embodiment, the second light-emitting compound and the second host material satisfy the relationship of the above mathematical formula (Mathematical Formula 3A), and therefore, when triplet excitons generated in the first light-emitting layer move to the second light-emitting layer, they transfer energy to molecules of the second host material, not to the second light-emitting compound having a higher triplet energy. Furthermore, triplet excitons generated by recombination of holes and electrons on the second host material do not transfer to the second light-emitting compound having a higher triplet energy. Triplet excitons generated by recombination on molecules of the second light-emitting compound quickly transfer energy to molecules of the second host material. Triplet excitons in the second host material do not transfer to the second light-emitting compound, but instead efficiently collide with each other on the second host material due to the TTF phenomenon, generating singlet excitons.
[0193] In the organic EL device according to this embodiment, it is preferable that the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second light-emitting compound satisfy the relationship of the following mathematical formula (Mathematical Formula 4). S1(H2)>S1(D2)…(Math 4)
[0194] In the organic EL device according to this embodiment, the second light-emitting compound and the second host material satisfy the relationship of the above mathematical formula (Mathematical Formula 4), and therefore the singlet energy of the second light-emitting compound is smaller than the singlet energy of the second host material. Therefore, the singlet excitons generated by the TTF phenomenon transfer energy from the second host material to the second light-emitting compound, contributing to the fluorescent emission of the second light-emitting compound.
[0195] In the organic EL device according to this embodiment, the second light-emitting compound is preferably a compound that does not contain an azine ring structure in the molecule.
[0196] In the organic EL device according to this embodiment, the second light-emitting compound is preferably not a boron-containing complex, and more preferably not a complex.
[0197] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a metal complex. Also, in the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a boron-containing complex.
[0198] In the organic EL device according to this embodiment, the second light-emitting layer preferably does not contain a phosphorescent material (dopant material). The second light-emitting layer preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex, such as an iridium complex, an osmium complex, or a platinum complex.
[0199] In the organic EL device according to this embodiment, the second light-emitting compound is preferably contained in the second light-emitting layer in an amount exceeding 1.1% by mass, i.e., the second light-emitting layer preferably contains the second light-emitting compound in an amount exceeding 1.1% by mass of the total mass of the second light-emitting layer, more preferably 1.2% by mass or more of the total mass of the second light-emitting layer, and even more preferably 1.5% by mass or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second light-emitting compound in an amount of 10 mass % or less of the total mass of the second light-emitting layer, more preferably 7 mass % or less of the total mass of the second light-emitting layer, and even more preferably 5 mass % or less of the total mass of the second light-emitting layer.
[0200] The second emitting layer preferably contains the second compound as a second host material in an amount of 60 mass% or more of the total mass of the second emitting layer, more preferably 70 mass% or more of the total mass of the second emitting layer, even more preferably 80 mass% or more of the total mass of the second emitting layer, still more preferably 90 mass% or more of the total mass of the second emitting layer, and even more preferably 95 mass% or more of the total mass of the second emitting layer. The second emitting layer preferably contains the second host material in an amount of 99% by mass or less of the total mass of the second emitting layer. When the second light-emitting layer contains a second host material and a second light-emitting compound, the upper limit of the total content of the second host material and the second light-emitting compound is 100% by mass.
[0201] Note that this embodiment does not exclude the case where the second light-emitting layer contains a material other than the second host material and the second light-emitting compound. The second light-emitting layer may contain only one type of second host material or two or more types of second light-emitting compounds.
[0202] In the organic EL device according to this embodiment, the thickness of the second emitting layer is preferably 5 nm or more, more preferably 15 nm or more. When the thickness of the second emitting layer is 5 nm or more, triplet excitons that have migrated from the first emitting layer to the second emitting layer can be easily prevented from returning to the first emitting layer. Furthermore, when the thickness of the second emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from the recombination site in the first emitting layer. In the organic EL device according to this embodiment, the thickness of the second emitting layer is preferably 25 nm or less, more preferably 20 nm or less, which can increase the density of triplet excitons in the second emitting layer and make the TTF phenomenon more likely to occur. In the organic EL device according to this embodiment, the thickness of the second light-emitting layer is preferably 5 nm or more and 25 nm or less.
[0203] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(DX) of the first light-emitting compound or the second light-emitting compound, the triplet energy T1(H1) of the first host material, and the triplet energy T1(H2) of the second host material satisfy the relationship shown in the following mathematical formula (Mathematical Formula 10). 2.6eV>T1(DX)>T1(H1)>T1(H2)…(Number 10)
[0204] The triplet energy T1(D1) of the first light-emitting compound preferably satisfies the relationship of the following mathematical formula (Formula 10A). 2.6 eV > T1(D1) > T1(H1) > T1(H2) …(Formula 10A)
[0205] The triplet energy T1(D2) of the second light-emitting compound preferably satisfies the relationship of the following mathematical formula (Formula 10B). 2.6 eV > T1(D2) > T1(H1) > T1(H2) …(Formula 10B)
[0206] In the organic EL element according to the present embodiment, it is preferable that the triplet energy T1(DX) of the first light-emitting compound or the second light-emitting compound and the triplet energy T1(H1) of the first host material satisfy the relationship of the following mathematical formula (Formula 11). 0 eV < T1(DX) - T1(H1) < 0.6 eV …(Formula 11)
[0207] The triplet energy T1(D1) of the first light-emitting compound preferably satisfies the relationship of the following mathematical formula (Formula 11A). 0 eV < T1(D1) - T1(H1) < 0.6 eV …(Formula 11A)
[0208] The triplet energy T1(D2) of the second light-emitting compound preferably satisfies the relationship of the following mathematical formula (Formula 11B). 0 eV < T1(D2) - T1(H2) < 0.8 eV …(Formula 11B)
[0209] In the organic EL element according to the present embodiment, it is preferable that the triplet energy T1(H1) of the first host material satisfies the relationship of the following mathematical formula (Formula 12). T1(H1) > 2.0 eV …(Formula 12)
[0210] In the organic EL element according to the present embodiment, it is also preferable that the triplet energy T1(H1) of the first host material satisfies the relationship of the following mathematical formula (Formula 12A) and also satisfies the relationship of the following mathematical formula (Formula 12B). T1(H1) > 2.10 eV …(Formula 12A) T1(H1)>2.15 eV...(Math 12B)
[0211] In the organic EL device according to this embodiment, when the triplet energy T1(H1) of the first host material satisfies the relationship of the above formula (12A) or (12B), triplet excitons generated in the first emitting layer are easily transferred to the second emitting layer, and reverse transfer from the second emitting layer to the first emitting layer is easily suppressed. As a result, singlet excitons are efficiently generated in the second emitting layer, and luminous efficiency is improved.
[0212] In the organic EL device according to this embodiment, the triplet energy T1(H1) of the first host material preferably satisfies the relationship of the following mathematical formula (12C), and also preferably satisfies the relationship of the following mathematical formula (12D). 2.08eV>T1(H1)>1.87eV …(math 12C) 2.05eV>T1(H1)>1.90eV …(math 12D)
[0213] In the organic EL element according to this embodiment, when the triplet energy T1(H1) of the first host material satisfies the relationship of the above-mentioned formula (12C) or (12D), the energy of the triplet excitons generated in the first emitting layer becomes small, and the lifetime of the organic EL element can be expected to be extended.
[0214] In the organic EL device according to this embodiment, the triplet energy T1(D1) of the first light-emitting compound preferably satisfies the relationship of the following mathematical formula (14A), and also preferably satisfies the relationship of the following mathematical formula (14B). 2.60eV>T1(D1) ...(Number 14A) 2.50eV>T1(D1) ... (Math 14B) When the first light-emitting layer contains the first light-emitting compound that satisfies the relationship of the above mathematical formula (14A) or (14B), the life of the organic EL device is extended.
[0215] In the organic EL device according to this embodiment, it is also preferable that the triplet energy T1(D2) of the second light-emitting compound satisfies the relationship of the following mathematical formula (14C), and it is also preferable that the triplet energy T1(D2) of the second light-emitting compound satisfies the relationship of the following mathematical formula (14D). 2.60eV>T1(D2)…(Number 14C) 2.50eV>T1(D2) ...(Number 14D) When the second light-emitting layer contains a compound that satisfies the relationship of the above-mentioned formula (14C) or (14D), the life of the organic EL device is extended.
[0216] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(H2) of the second host material satisfies the relationship of the following mathematical formula (Mathematical Formula 13). T1(H2)≧1.9 eV … (Equation 13)
[0217] (Third light-emitting layer) The organic EL device according to this embodiment may further include a third light-emitting layer. The third emitting layer contains a third host material, and the first host material, second host material, and third host material are different from one another. The third emitting layer contains at least a third emitting compound that emits light with a maximum peak wavelength of 500 nm or less, and the first emitting compound, second emitting compound, and third emitting compound are the same as or different from one another. It is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(H3) of the third host material satisfy the relationship of the following mathematical formula (Mathematical Formula 1A). T1(H1)>T1(H3) ... (Math 1A)
[0218] When the organic EL device according to this embodiment includes a third light-emitting layer, it is preferable that the triplet energy T1(H2) of the second host material and the triplet energy T1(H3) of the third host material satisfy the relationship shown in the following mathematical formula (Mathematical Formula 1B). T1(H2)>T1(H3)…(Math 1B)
[0219] In the organic EL device according to this embodiment, the first light-emitting layer and the second light-emitting layer are preferably in direct contact with each other.
[0220] In this specification, a layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact with each other" can include, for example, any of the following embodiments (LS1), (LS2), and (LS3). (LS1) An embodiment in which a region in which both the first host material and the second host material are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer. (LS2) When the first emitting layer and the second emitting layer contain a light-emitting compound, a region in which the first host material, the second host material, and the light-emitting compound are mixed is generated during the process of vapor-depositing the compound for the first emitting layer and the process of vapor-depositing the compound for the second emitting layer, and this region is present at the interface between the first emitting layer and the second emitting layer. (LS3) When the first emitting layer and the second emitting layer contain a light-emitting compound, a region made of the light-emitting compound, a region made of the first host material, or a region made of the second host material is generated during the process of vapor-depositing the compound for the first emitting layer and the compound for the second emitting layer, and the region is present at the interface between the first emitting layer and the second emitting layer.
[0221] When the organic EL device according to this embodiment includes a third light-emitting layer, it is preferable that the first light-emitting layer and the second light-emitting layer are in direct contact with each other, and that the second light-emitting layer and the third light-emitting layer are in direct contact with each other.
[0222] In this specification, a layer structure in which "the second light-emitting layer and the third light-emitting layer are in direct contact with each other" can include, for example, any of the following embodiments (LS4), (LS5), and (LS6). (LS4) An embodiment in which a region in which both the second host material and the third host material are mixed is generated during the process of vapor-depositing the compound for the second emitting layer and the compound for the third emitting layer, and this region is present at the interface between the second emitting layer and the third emitting layer. (LS5) When the second emitting layer and the third emitting layer contain a luminescent compound, a region in which the second host material, the third host material, and the luminescent compound are mixed is generated during the process of vapor-depositing the compound for the second emitting layer and the process of vapor-depositing the compound for the third emitting layer, and this region is present at the interface between the second emitting layer and the third emitting layer. (LS6) When the second emitting layer and the third emitting layer contain a luminescent compound, a region made of the luminescent compound, a region made of the second host material, or a region made of the third host material is generated during the process of vapor-depositing the compound for the second emitting layer and the compound for the third emitting layer, and the region is present at the interface between the second emitting layer and the third emitting layer.
[0223] For example, in the organic EL device according to this embodiment, a first emitting layer containing a first compound represented by the general formula (1) or the like as a first host material and a second emitting layer containing a second compound represented by the general formula (2) or the like as a second host material may be in direct contact with each other. Stacking the first emitting layer and the second emitting layer in this manner also makes it possible to effectively utilize the generated singlet excitons and triplet excitons, thereby improving the luminous efficiency of the organic EL device.
[0224] (Layer not containing a light-emitting compound) Furthermore, the stacked light-emitting unit of the organic EL element according to this embodiment preferably further includes a layer (sometimes referred to as an intervening layer) that does not contain a light-emitting compound and is disposed between the organic layers.
[0225] When the stacked light-emitting unit of the organic EL element according to this embodiment has a layer (intervening layer) that does not contain a light-emitting compound, the layer (intervening layer) that does not contain a light-emitting compound is preferably disposed between the first light-emitting layer and the second light-emitting layer.
[0226] The intervening layer preferably does not contain metal atoms. The intervening layer contains an organic material, which is preferably not a light-emitting compound. Examples of organic materials contained in the intervening layer include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 3) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.
[0227] The organic material contained in the intervening layer 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.
[0228] When the intervening layer contains a plurality of organic materials, the content of each organic material is preferably 10% by mass or more of the total mass of the intervening layer. The intervening layer preferably contains the organic material in an amount of 60% by mass or more of the total mass of the intervening layer, more preferably 70% by mass or more of the total mass of the intervening layer, even more preferably 80% by mass or more of the total mass of the intervening layer, even more preferably 90% by mass or more of the total mass of the intervening layer, and even more preferably 95% by mass or more of the total mass of the intervening layer. The intervening layer may contain only one type of organic material, or may contain two or more types of organic materials. When the intervening layer contains two or more organic materials, the upper limit of the total content of the two or more organic materials is 100% by mass. It should be noted that this embodiment does not exclude the case where the intervening layer contains a material other than the organic material.
[0229] The intervening layer may be composed of a single layer or may be composed of two or more layers laminated together.
[0230] The thickness of the intervening layer is not particularly limited, but is preferably 3 nm or more and 15 nm or less, and more preferably 5 nm or more and 10 nm or less per layer.
[0231] In the first compound and the second compound, it is preferable that the groups described as "substituted or unsubstituted" are both "unsubstituted" groups.
[0232] In this specification, the term "host material" refers to a material that is contained in, for example, "50% by mass or more of a layer." Thus, for example, the first light-emitting layer contains a first compound represented by the following general formula (1) in an amount of 50% by mass or more of the total mass of the first light-emitting layer. The second light-emitting layer contains, for example, a second compound represented by the following general formula (2) in an amount of 50% by mass or more of the total mass of the second light-emitting layer.
[0233] (phenanthroline compounds) The phenanthroline compound has at least one group represented by the following general formula (21) and is preferably a compound represented by the following general formula (20).
[0234] [ka]
[0235] (In the general formula (20), X 21 ~X 28 are each independently a nitrogen atom, CR 21 or a carbon atom bonded to the group represented by the general formula (21), X 21 ~X 28 at least one of which is a carbon atom bonded to the group represented by general formula (21), When a plurality of groups represented by the general formula (21) are present, the plurality of groups represented by the general formula (21) are the same or different from each other, Multiple R 21 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 21 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 931 a group represented by -COOR 932 a group represented by -S(=O)2R 933 a group represented by -B(R 934 )(R 935 ) a group represented by -P(=O)(R 936 )(R 937 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0236] (In the general formula (21), Ar2 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, p is 1, 2, 3, 4 or 5; When two or more Ar2's are present, the two or more Ar2's are the same or different from each other, L2 is a single bond or a linking group; L2 as a linking group is a substituted or unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 50 carbon atoms; a substituted or unsubstituted polyvalent aromatic hydrocarbon group having 6 to 50 ring carbon atoms, a substituted or unsubstituted polyvalent heterocyclic group having 5 to 50 ring atoms, or a polyvalent multiple linking group formed by bonding two or three groups selected from the polyvalent aromatic hydrocarbon ring group and the polyvalent heterocyclic group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group may be the same or different, and adjacent groups may be bonded to each other to form a ring or may not be bonded to each other; Ar2 and L2 as a linking group are bonded to each other to form a ring or are not bonded to each other, L2 as a linking group and X adjacent to the carbon atom bonded to L2 21 ~X 28 Either carbon atom or CR 21 R 21 and are bonded to each other to form a ring or are not bonded to each other, In the general formula (21), * indicates the bonding position to the ring represented by the general formula (20).
[0237] (In the phenanthroline compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 931 , R 932 , R 933 , R 934 , R 935 , R936 and R 937 are each independently, hydrogen atoms, 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, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 931 If there are multiple R 931 are the same or different from each other, R 932 If there are multiple R 932 are the same or different from each other, R 933 If there are multiple R 933 are the same or different from each other, R 934 If there are multiple R 934 are the same or different from each other, R 935 If there are multiple R 935 are the same or different from each other, R 936 If there are multiple R 936 are the same or different from each other, R 937 If there are multiple R 937 are either identical or different.)
[0238] As used herein, —O—(R 904 ) is a group represented by R 904 When is a hydrogen atom, it is a hydroxy group. As used herein, -S-(R 905 ) is a group represented by R 905 When is a hydrogen atom, it is a thiol group. As used herein, -S(=O)R 933 The group represented by R 933 When is a substituent, it is a substituted sulfo group. As used herein, -B(R 934 )(R 935 ) is a group represented by R 934 and R 935 is a substituent, it is a substituted boryl group. As used herein, -P(=O)(R 936 )(R 937 ) is a group represented by R 936 and R 937 is a substituent, it is a substituted phosphine oxide group, and R 936 and R 937 When is an aryl group, it is an arylphosphoryl group.
[0239] The number of carbon atoms in the "unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon group" described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification. The number of ring carbon atoms of the "unsubstituted polyvalent aromatic hydrocarbon group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification. The "unsubstituted polyvalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
[0240] The heterocyclic group having 5 to 50 ring atoms in Ar2 of the general formula (21) preferably contains a substituted or unsubstituted group derived from the ring structure represented by the general formula (20).
[0241] X in the general formula (20) 21 and X 28 is also preferably a carbon atom bonded to the group represented by the general formula (21). X in the general formula (20) 21 and X 28 is a carbon atom bonded to the group represented by the general formula (21), and X 21 and X 28 It is also preferred that the other of the groups is a carbon atom bonded to a hydrogen atom.
[0242] X in the general formula (20) 21 ~X 28 are each independently, CR 21 Alternatively, it is preferably a carbon atom bonded to the group represented by the general formula (21). X in the general formula (20) 21 ~X 28 In the formula (21), the carbon atoms other than the carbon atom bonded to the group represented by the formula (21) are CR 21 That is, the compound represented by the general formula (20) is preferably a 1,10-phenanthroline derivative.
[0243] It is also preferable that Ar2 in the general formula (21) is a substituted or unsubstituted fused aromatic hydrocarbon group having 8 to 20 ring carbon atoms.
[0244] The fused aromatic hydrocarbon group having 8 to 20 ring carbon atoms is preferably a group derived from any aromatic hydrocarbon selected from the group consisting of, for example, naphthalene, anthracene, acephenanthrylene, aceanthrylene, benzanthracene, triphenylene, pyrene, chrysene, naphthacene, fluorene, phenanthrene, fluoranthene, and benzofluoranthene.
[0245] It is also preferable that Ar2 in the general formula (21) is a substituted or unsubstituted anthryl group.
[0246] It is also preferable that Ar2 in the general formula (21) is a substituted or unsubstituted heterocyclic group having 5 to 40 ring carbon atoms.
[0247] It is also preferable that Ar2 in the general formula (21) is a substituted or unsubstituted group derived from the ring structure represented by the general formula (20).
[0248] It is also preferable that Ar2 in the general formula (21) is a group represented by the following general formula (23).
[0249] [ka]
[0250] (In the general formula (23), X 21 ~X 28 are each independently a nitrogen atom, CR 21 , a group represented by the general formula (21) or L 22 Or L 23 is a carbon atom bonded to L 21 is a linking group, and L as a linking group 21 represents a substituted or unsubstituted linear, branched or cyclic trivalent aliphatic hydrocarbon group having 1 to 50 carbon atoms, a substituted or unsubstituted trivalent aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted trivalent heterocyclic group having 5 to 50 ring atoms, L 22and L 23 are each independently a single bond or a linking group, and L as a linking group 22 and L 23 are each independently a substituted or unsubstituted straight-chain, branched-chain, or cyclic divalent aliphatic hydrocarbon group having 1 to 50 carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
[0251] In the general formula of the phenanthroline compound, X 21 If there are multiple X 21 are the same or different from each other, X 22 If there are multiple X 22 are the same or different from each other, X 23 If there are multiple X 23 are the same or different from each other, X 24 If there are multiple X 24 are the same or different from each other, X 25 If there are multiple X 25 are the same or different from each other, X 26 If there are multiple X 26 are the same or different from each other, X 27 If there are multiple X 27 are the same or different from each other, X 28 If there are multiple X 28 are the same or different from each other.
[0252] X in the general formula (23) 21 ~X 28 are each independently a nitrogen atom, CR 21 , or L 22 Or L 23 Preferably, the carbon atom bonded to CR 21 , or L22 Or L 23 It is more preferable that the carbon atom bonded to
[0253] The phenanthroline compound is also preferably a compound represented by the following general formula (24).
[0254] [ka]
[0255] (In the general formula (24), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with Multiple R 22 are each independently R in the general formula (20). 21 is synonymous with L2 has the same meaning as L2 in the general formula (21), p is 1, 2, 3, 4 or 5; Multiple R 22 and L2 is bonded to any of the carbon atoms 1 to 10 of the anthracene ring.
[0256] The phenanthroline compound is also preferably a compound represented by the following general formula (24A).
[0257] [ka]
[0258] (In the general formula (24A), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with Multiple R 22 are each independently R in the general formula (20). 21 is synonymous with L2 has the same meaning as L2 in the general formula (21).
[0259] The phenanthroline compound is also preferably a compound represented by the following general formula (24B).
[0260] [ka]
[0261] (In the general formula (24B), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with Multiple R 22 are each independently R in the general formula (20). 21 is synonymous with L2 has the same meaning as L2 in the general formula (21).
[0262] The phenanthroline compound is also preferably a compound represented by the following general formula (25).
[0263] [ka]
[0264] (In the general formula (25), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with Multiple R 22 are each independently R in the general formula (20). 21 is synonymous with L2 has the same meaning as L2 in the general formula (21), p is 1, 2, 3, 4 or 5; Multiple R 22 and L2 is bonded to any of the carbon atoms 2 to 9 of the phenanthroline ring.
[0265] The phenanthroline compound is also preferably a compound represented by the following general formula (25A).
[0266] [ka]
[0267] (In the general formula (25A), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with Multiple R 22 are each independently R in the general formula (20). 21 is synonymous with L2 has the same meaning as L2 in the general formula (21).
[0268] It is also preferable that L2 in the general formulae (24), (24A), (24B), (25), and (25A) is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
[0269] The phenanthroline compound is also preferably a compound represented by the following general formula (25B).
[0270] [ka]
[0271] (In the general formula (25B), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with Multiple R 22 are each independently R in the general formula (20). 21 is synonymous with L3 is a linking group, and L3 as a linking group is a substituted or unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 50 carbon atoms; a substituted or unsubstituted polyvalent amino group, a substituted or unsubstituted polyvalent aromatic hydrocarbon ring group having 6 to 50 ring carbon atoms, a substituted or unsubstituted polyvalent heterocyclic group having 5 to 50 ring atoms, or a polyvalent multiple linking group formed by bonding two or three groups selected from the polyvalent aromatic hydrocarbon ring group and the polyvalent heterocyclic group, the aromatic hydrocarbon ring group and the heterocyclic group constituting L3 as the multiple linking group are the same or different, and adjacent groups are bonded to each other to form a ring or are not bonded to each other, p is 1, 2, 3, 4 or 5; Multiple R 22 and L3 is bonded to any of the carbon atoms at positions 1 to 10 of the phenanthrene ring.
[0272] The phenanthroline compound is also preferably a compound represented by the following general formula (25C).
[0273] [ka]
[0274] (In the general formula (25C), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with R 221 ~R 230 One of the R is a single bond that bonds to L3, and the other R is not a single bond that bonds to L3. 221 ~R 230 are each independently R in the general formula (20). 21 is synonymous with L3 is a linking group, and L3 as the linking group has the same meaning as L3 as the linking group in general formula (25B). p is 1, 2, 3, 4 or 5.
[0275] The phenanthroline compound is also preferably a compound represented by the following general formula (25D).
[0276] [ka]
[0277] (In the general formula (25D), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with R 221 ~R 232 One of the R is a single bond that bonds to L3, and the other R is not a single bond that bonds to L3. 221 ~R 232 are each independently R in the general formula (20). 21 is synonymous with L3 is a linking group, and L3 as the linking group has the same meaning as L3 as the linking group in general formula (25B). p is 1, 2, 3, 4 or 5.
[0278] The phenanthroline compound is also preferably a compound represented by the following general formula (25E).
[0279] [ka]
[0280] (In the general formula (25E), Multiple R 21 are each independently R in the general formula (20). 21 is synonymous with R 221 ~R 230 One of the R is a single bond that bonds to L3, and the other R is not a single bond that bonds to L3. 221 ~R 230 are each independently R in the general formula (20). 21 is synonymous with L3 is a linking group, and L3 as the linking group has the same meaning as L3 as the linking group in general formula (25B). p is 1, 2, 3, 4 or 5.
[0281] It is also preferable that L3 in the general formulae (25B), (25C), (25D), and (25E) is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
[0282] (Method of producing phenanthroline compound) The phenanthroline compound can be produced by a known method. Alternatively, the phenanthroline compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target product.
[0283] (Specific Examples of Phenanthroline Compounds) Specific examples of the phenanthroline compound include the following compounds, however, the present invention is not limited to these specific examples of the phenanthroline compound.
[0284] [ka]
[0285] [ka]
[0286] [ka]
[0287] [ka]
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[0289] [ka]
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[0291]
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[0292]
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[0300] [ka]
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[0303] (First Host Material, Second Host Material, and Third Host Material) In the organic EL device according to this embodiment, examples of the first host material, the second host material, and the third host material include a first compound represented by the following general formula (1), general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X), or general formula (16X), and a second compound represented by the following general formula (2). The first compound can also be used as the first host material and the second host material. In this case, the compound represented by the following general formula (1), or the following general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X), or general formula (16X), used as the second host material, may be referred to as the second compound for convenience.
[0304] (First Host Material) In the organic EL device according to this embodiment, it is also preferable that the first host material has, in its molecule, a structure satisfying the above-mentioned condition (ii), i.e., a linking structure including a benzene ring and a naphthalene ring linked by a single bond, and that the benzene ring and the naphthalene ring in the linking structure are each independently further fused with a single ring or a fused ring or are not fused with a single ring, and that the benzene ring and the naphthalene ring in the linking structure are further linked by a crosslink at at least one portion other than the single bond. When the first host material has a linking structure including such a crosslink, it is expected that deterioration of the chromaticity of the organic EL device can be suppressed. In this case, the first host material only needs to have, as a minimum unit in the molecule, a linked structure containing a benzene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X1) or (X2) (sometimes referred to as a benzene-naphthalene linked structure), and the benzene ring may be further fused with a single ring or a fused ring, or the naphthalene ring may be further fused with a single ring or a fused ring. For example, even when the first host material has, in the molecule, a linked structure containing a naphthalene ring and a naphthalene ring linked by a single bond, as represented by the following formula (X3), (X4), or (X5) (sometimes referred to as a naphthalene-naphthalene linked structure), one of the naphthalene rings contains a benzene ring, and therefore contains a benzene-naphthalene linked structure.
[0305] [ka]
[0306] In the organic EL device according to this embodiment, it is also preferable that the crosslink contains a double bond, i.e., the benzene ring and the naphthalene ring are further linked by a crosslinked structure containing a double bond at a portion other than the single bond.
[0307] When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge at at least one portion other than a single bond, for example, in the case of the formula (X1), the linked structure (fused ring) is represented by the following formula (X11), and in the case of the formula (X3), the linked structure (fused ring) is represented by the following formula (X31). When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge containing a double bond at a portion other than the single bond, for example, in the case of the formula (X1), the linked structure (fused ring) is represented by the following formula (X12); in the case of the formula (X2), the linked structure (fused ring) is represented by the following formula (X21), formula (X22), or formula (X23); in the case of the formula (X4), the linked structure (fused ring) is represented by the following formula (X41); and in the case of the formula (X5), the linked structure (fused ring) is represented by the following formula (X51). When the benzene ring and the naphthalene ring in the benzene-naphthalene linked structure are further linked by a bridge containing a heteroatom (e.g., an oxygen atom) in at least one portion other than the single bond, for example, in the case of the above formula (X1), the linked structure (fused ring) is represented by the following formula (X13).
[0308] [ka]
[0309] In the organic EL device according to this embodiment, it is also preferable that the first host material has a structure satisfying the above-mentioned condition (i), i.e., a biphenyl structure in which a first benzene ring and a second benzene ring are linked by a single bond in the molecule, and the first benzene ring and the second benzene ring in the biphenyl structure are further linked by a bridge at at least one part other than the single bond.
[0310] In the organic EL device according to this embodiment, it is also preferable that the first host material has a structure satisfying the above condition (i) in its molecule, and that the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the above bridge at a portion other than the single bond. When the first host material has a biphenyl structure containing such a bridge, it is expected that deterioration in chromaticity of the organic EL device can be suppressed.
[0311] In the organic EL device according to this embodiment, it is also preferable that the first host material has a structure that satisfies the above condition (i) in the molecule, and that the first benzene ring and the second benzene ring in the biphenyl structure are further linked by the above bridge at two portions other than the single bond.
[0312] In the organic EL device according to this embodiment, it is also preferable that the first host material has a structure that satisfies the above condition (i) in the molecule, and the crosslink contains a double bond. In the organic EL device according to this embodiment, it is also preferable that the first host material has a structure that satisfies the above condition (i) in the molecule, and the crosslink does not contain a double bond.
[0313] In the organic EL device according to this embodiment, it is also preferable that the first host material has a structure satisfying the above condition (i) in its molecule, the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the bridge at two portions other than the single bond, and the bridge does not contain a double bond. When the first host material has a biphenyl structure containing such a bridge, it is expected that deterioration in chromaticity of the organic EL device can be suppressed.
[0314] For example, when the first benzene ring and the second benzene ring in the biphenyl structure represented by the following formula (BP1) are further linked by a bridge at at least one moiety other than a single bond, the biphenyl structure becomes a linked structure (fused ring) such as those of the following formulae (BP11) to (BP15).
[0315] [ka]
[0316] The formula (BP11) is a structure in which the units are linked by a bridge that does not contain a double bond in one part other than the single bond. The formula (BP12) is a structure in which the units are linked by a bridge containing a double bond in one part other than the single bond. The formula (BP13) has a structure in which the two parts other than the single bond are linked by a bridge that does not contain a double bond. The formula (BP14) has a structure in which one of the two moieties other than the single bond is linked by a bridge that does not contain a double bond, and the other of the two moieties other than the single bond is linked by a bridge that contains a double bond. The formula (BP15) has a structure in which the two moieties other than the single bond are linked by a bridge containing a double bond.
[0317] (First Compound) In the organic EL device according to this embodiment, the first host material preferably has at least one group represented by the following general formula (11) and is a first compound represented by the following general formula (1):
[0318] [ka]
[0319] (In the general formula (1), R 101 ~R 110 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (11), However, R 101 ~R 110 at least one of is a group represented by the general formula (11), When a plurality of groups represented by the general formula (11) are present, the plurality of groups represented by the general formula (11) are the same or different from each other, L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx is 0, 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are identical to or different from each other, Ar 101 If there are two or more, there are two or more Ar 101 are identical to or different from each other, In the general formula (11), * indicates the bonding position to the pyrene ring in the general formula (1).
[0320] (In the first compound according to this embodiment, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R907 , R 801 and R 802 are each independently, hydrogen atoms, 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, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are either identical or different.)
[0321] In the organic EL device according to this embodiment, the group represented by the general formula (11) is preferably a group represented by the following general formula (111).
[0322] [ka]
[0323] (In the general formula (111), X1 is a CR 123 R 124 , oxygen atom, sulfur atom, or NR 125 and L 111 and L 112 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ma is 0, 1, 2, 3 or 4; mb is 0, 1, 2, 3 or 4; ma+mb is 0, 1, 2, 3 or 4, Ar 101 represents Ar in the general formula (11). 101 is synonymous with R 121 , R 122 , R 123 , R 124 and R 125 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 121 are identical to or different from each other, md is 3, The Three Rs 122 are either identical or different.)
[0324] In the group represented by the general formula (111), L is located at any one of positions *1 to *4 among positions *1 to *8 of carbon atoms in the ring structure represented by the following general formula (111a): 111 is bonded, and R is placed in the remaining three positions of *1 to *4. 121 is bonded, and L is at any one of the positions *5 to *8. 112 is bonded, and R is placed in the remaining three positions of *5 to *8. 122 are combined.
[0325] [ka]
[0326] For example, in the group represented by the general formula (111), L 111 is bonded to the carbon atom marked with *2 in the ring structure represented by the general formula (111a), and L 112 When is bonded to the carbon atom at *7 in the ring structure represented by the general formula (111a), the group represented by the general formula (111) is represented by the following general formula (111b).
[0327] [ka]
[0328] (In the general formula (111b), X1, L 111 , L 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and R 125 each independently represents X1, L in the general formula (111). 111 , L 112 , ma, mb, Ar 101 , R 121 , R 122 , R 123 , R 124 and R 125 is synonymous with Multiple R 121 are identical to or different from each other, Multiple R 122 are either identical or different.)
[0329] In the organic EL device according to this embodiment, the group represented by the general formula (111) is preferably a group represented by the general formula (111b).
[0330] In the organic EL element according to this embodiment, ma is 0, 1 or 2; Preferably, mb is 0, 1 or 2.
[0331] In the organic EL element according to this embodiment, ma is 0 or 1, mb is preferably 0 or 1.
[0332] In the organic EL element according to this embodiment, Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0333] In the organic EL element according to this embodiment, Ar101 teeth, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, or A substituted or unsubstituted fluorenyl group is preferred.
[0334] In the organic EL element according to this embodiment, Ar 101 is also preferably a group represented by the following general formula (12), general formula (13) or general formula (14).
[0335] [ka]
[0336] (In the general formula (12), general formula (13) and general formula (14), R 111 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 124 a group represented by -COOR 125 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * in the general formula (12), general formula (13) and general formula (14) represents L in the general formula (11). 101 or the bonding position of L in the general formula (111) or the general formula (111b). 112 )
[0337] In the organic EL device according to this embodiment, the first compound is preferably represented by the following general formula (101).
[0338] [ka]
[0339] (In the general formula (101), R 101 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R 101 ~R 110 One of them is L 101 indicates the bond position with R 111 ~R 120 One of them is L 101 indicates the bonding position with L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, mx is 0, 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are either identical or different.)
[0340] In the first compound represented by the general formula (101), R 101 ~R 110 , and R 111 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, However, R 101 ~R 110 One of them is L 101 indicates the bond position with R 111 ~R 120 One of them is L 101 indicates the bonding position with L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 24 ring atoms, mx is 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are preferably the same as or different from each other.
[0341] In the organic EL device according to this embodiment, the first compound is preferably represented by the following general formula (1010), general formula (1011), general formula (1012), general formula (1013), general formula (1014), or general formula (1015).
[0342] [ka]
[0343] [ka]
[0344] [ka]
[0345] [ka]
[0346] [ka]
[0347] [ka]
[0348] (In the general formulae (1010) to (1015), R 101 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, mx is 0, 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are either identical or different.)
[0349] The compound represented by the general formula (1010) is R 103 L 101 indicates the bond position with R 120 L 101 This corresponds to a compound in which the bonding position is indicated. The compound represented by the general formula (1011) is R 103 L 101 indicates the bond position with R 111 L 101 This corresponds to a compound in which the bonding position is indicated. The compound represented by the general formula (1012) is R 103 L 101 indicates the bond position with R 118 L 101 This corresponds to a compound in which the bonding position is indicated. The compound represented by the general formula (1013) is R 102 L 101 indicates the bond position with R 111 L101 This corresponds to a compound in which the bonding position is indicated. The compound represented by the general formula (1014) is R 102 L 101 indicates the bond position with R 118 L 101 This corresponds to a compound in which the bonding position is indicated. The compound represented by the general formula (1015) is R 105 L 101 indicates the bond position with R 118 L 101 This corresponds to a compound in which the bonding position is indicated.
[0350] In the organic EL device according to this embodiment, the first compound is preferably represented by the general formula (1010).
[0351] In the organic EL element according to this embodiment, L 101 R is not a bond position with 101 ~R 110 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0352] In the organic EL element according to this embodiment, L 101 R is not a bond position with 101 ~R 110 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.
[0353] In the organic EL element according to this embodiment, L 101 R is not a bond position with101 ~R 110 is preferably a hydrogen atom.
[0354] In the organic EL element according to this embodiment, L 101 R is not a bond position with 111 ~R 120 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0355] In the organic EL element according to this embodiment, L 101 R is not a bond position with 111 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.
[0356] In the organic EL element according to this embodiment, L 101 R is not a bond position with 111 ~R 120 is preferably a hydrogen atom.
[0357] In the organic EL element according to this embodiment, L 101 teeth, a single bond, or It is preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
[0358] In the organic EL element according to this embodiment, L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or It is also preferably a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.
[0359] In the organic EL element according to this embodiment, L 101 teeth, a single bond, or A substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms is also preferred.
[0360] In the organic EL element according to this embodiment, L 101 teeth, A substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms is also preferred.
[0361] In the organic EL element according to this embodiment, L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms, or It is also preferably a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms.
[0362] In the organic EL element according to this embodiment, L 101 teeth, a single bond, or A substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms is also preferred.
[0363] In the organic EL element according to this embodiment, L 101 teeth, A substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms is also preferred.
[0364] In the organic EL device according to this embodiment, mx is preferably 1, 2, or 3.
[0365] In the organic EL device according to this embodiment, mx is also preferably 1 or 2.
[0366] In the organic EL element according to this embodiment, mx is 1, 2, or 3; L 101 teeth, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or It is also preferably a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.
[0367] In the organic EL element according to this embodiment, mx is 1 or 2, L 101 teeth, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or It is also preferably a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms.
[0368] In the organic EL element according to this embodiment, mx is 1 or 2, L 101 is also preferably a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.
[0369] In the organic EL element according to this embodiment, The first compound is preferably represented by the following general formula (102).
[0370] [ka]
[0371] (In the general formula (102), R 101 ~R 120 are each independently R in the general formula (101). 101 ~R 120 is synonymous with However, R 101 ~R 110 One of them is L 111 indicates the bond position with R 111 ~R 120 One of them is L 112 indicates the bonding position with X1 is a CR 123 R 124 , oxygen atom, sulfur atom, or NR 125 and L 111 and L 112 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ma is 0, 1, 2, 3 or 4; mb is 0, 1, 2, 3 or 4; ma+mb is 0, 1, 2, 3 or 4, R 121 , R 122 , R 123 , R 124 and R 125 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 121 are identical to or different from each other, md is 3, The Three Rs 122 are either identical or different.)
[0372] In the compound represented by the general formula (102), ma is 0, 1 or 2; Preferably, mb is 0, 1 or 2.
[0373] In the compound represented by the general formula (102), ma is 0 or 1, mb is preferably 0 or 1.
[0374] In the compound represented by the general formula (102), L 111 and L 112 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms, or It is preferably a substituted or unsubstituted divalent heterocyclic group having 5 to 24 ring atoms.
[0375] In the compound represented by the general formula (102), ma is 1, 2, or 3; mb is 1, 2, or 3; ma+mb is 2, 3, or 4,
[0376] In the compound represented by the general formula (102), ma is 1 or 2, Preferably, mb is 1 or 2.
[0377] In the compound represented by the general formula (102), ma is 1, Preferably, mb is 1.
[0378] In the organic EL element according to this embodiment, L 111 R is not a bond position with 101 ~R 110 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0379] In the organic EL element according to this embodiment, L 111 R is not a bond position with 101 ~R 110 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.
[0380] In the organic EL element according to this embodiment, L 111 R is not a bond position with 101 ~R 110 is preferably a hydrogen atom.
[0381] In the organic EL element according to this embodiment, L 112 R is not a bond position with 111 ~R 120 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0382] In the organic EL element according to this embodiment, L 112 R is not a bond position with 111 ~R 120 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.
[0383] In the organic EL element according to this embodiment, L 112 R is not a bond position with 111 ~R 120 is preferably a hydrogen atom.
[0384] In the organic EL element according to this embodiment, R 101 ~R 110 It is preferable that two or more of the above are groups represented by the general formula (11).
[0385] In the organic EL element according to this embodiment, R 101 ~R 110 At least two of the groups are groups represented by the general formula (11), and Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0386] In the organic EL element according to this embodiment, Ar 101 is not a substituted or unsubstituted pyrenyl group, L 101 is not a substituted or unsubstituted pyrenylene group, R which is not a group represented by the general formula (11) 101 ~R 110 The substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms as represented by is preferably not a substituted or unsubstituted pyrenyl group.
[0387] In the organic EL element according to this embodiment, R which is not a group represented by the general formula (11) 101 ~R 110 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0388] In the organic EL element according to this embodiment, R which is not a group represented by the general formula (11) 101 ~R 110 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.
[0389] In the organic EL device according to this embodiment, R 101 ~R 110 is preferably a hydrogen atom.
[0390] In the first compound and the second compound, it is preferable that the groups described as "substituted or unsubstituted" are both "unsubstituted" groups.
[0391] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 Two of these are groups represented by general formula (11).
[0392] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 Three of these are groups represented by general formula (11).
[0393] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 Among them, four are groups represented by general formula (11).
[0394] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 One of the groups is a group represented by general formula (11), and mx is 1 or more.
[0395] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 one of the groups is a group represented by general formula (11), mx is 0, and Ar 101 is a substituted or unsubstituted aryl group.
[0396] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 one of the groups is a group represented by general formula (11), mx is 0, and Ar 101 is a substituted or unsubstituted heterocyclic group containing a nitrogen atom.
[0397] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 one of the groups is a group represented by general formula (11), mx is 0, and Ar 101 is a substituted or unsubstituted heterocyclic group containing a sulfur atom.
[0398] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 one of the groups is a group represented by general formula (11), mx is 0, and Ar 101 is a substituted or unsubstituted furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and It is a diazanaphthobenzofuranyl group.
[0399] In the organic EL element according to this embodiment, For example, R in the first compound represented by the general formula (1) 101 Or R 110 one of the groups is a group represented by general formula (11), mx is 0, and Ar 101 is an unsubstituted furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and and at least one group selected from the group consisting of diazanaphthobenzofuranyl groups.
[0400] In the organic EL device according to this embodiment, for example, R 101 Or R 110 one of the groups is a group represented by general formula (11), mx is 0, and Ar 101 is a substituted or unsubstituted dibenzofuranyl group.
[0401] In the organic EL device according to this embodiment, for example, R 101 Or R 110 one of the groups is a group represented by general formula (11), mx is 0, and Ar 101 is an unsubstituted dibenzofuranyl group.
[0402] In the organic EL device according to this embodiment, for example, mx in the first compound represented by the general formula (101) is 2 or more.
[0403] In the organic EL device according to this embodiment, for example, mx in the first compound represented by the general formula (101) is 1 or more, and L 101 is an arylene group having 6 to 24 ring carbon atoms or a divalent heterocyclic group having 5 to 24 ring atoms.
[0404] In the organic EL device according to this embodiment, for example, mx in the first compound represented by the general formula (101) is 1 or more, and L 101 is an arylene group having 6 to 18 ring carbon atoms or a divalent heterocyclic group having 5 to 18 ring atoms.
[0405] A compound represented by the general formula (1X) In the organic EL device according to this embodiment, the first compound is also preferably a compound represented by the following general formula (1X).
[0406] [ka]
[0407] (In the general formula (1X), R 101 ~R 112 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (11X), However, R 101 ~R 112 at least one of is a group represented by the general formula (11X), When a plurality of groups represented by the general formula (11X) are present, the plurality of groups represented by the general formula (11X) are the same or different from each other, L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx is 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are identical to or different from each other, Ar 101 If there are two or more, there are two or more Ar 101 are identical to or different from each other, The symbol * in the general formula (11X) indicates the bonding position to the benz[a]anthracene ring in the general formula (1X).
[0408] In the organic EL device according to this embodiment, the group represented by the general formula (11X) is preferably a group represented by the following general formula (111X).
[0409] [ka]
[0410] (In the general formula (111X), X1 is a CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 and L 111 and L 112 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ma is 1, 2, 3 or 4; mb is 1, 2, 3 or 4; ma+mb is 2, 3, or 4, Ar 101 represents Ar in the general formula (11). 101 is synonymous with R 141 , R 142 , R 143 , R 144 and R 145 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 141 are identical to or different from each other, md is 3, The Three Rs 142 are either identical or different.)
[0411] In the group represented by the general formula (111X), L is located at any one of positions *1 to *4 among positions *1 to *8 of carbon atoms in the ring structure represented by the following general formula (111aX): 111 is bonded, and R is placed in the remaining three positions of *1 to *4. 141 is bonded, and L is at any one of the positions *5 to *8. 112 is bonded, and R is placed in the remaining three positions of *5 to *8. 142 are combined.
[0412] [ka]
[0413] For example, in the group represented by the general formula (111X), L 111 is bonded to the carbon atom marked with *2 in the ring structure represented by the general formula (111aX), and L 112 When is bonded to the carbon atom at *7 in the ring structure represented by the general formula (111aX), the group represented by the general formula (111X) is represented by the following general formula (111bX).
[0414] [ka]
[0415] (In the general formula (111bX), X1, L 111 , L 112 , ma, mb, Ar 101 , R 141 , R 142 , R 143 , R 144 and R 145 each independently represents X1, L in the general formula (111X). 111 , L 112 , ma, mb, Ar 101 , R 141 , R 142, R 143 , R 144 and R 145 is synonymous with Multiple R 141 are identical to or different from each other, Multiple R 142 are either identical or different.)
[0416] In the organic EL device according to this embodiment, the group represented by the general formula (111X) is preferably a group represented by the general formula (111bX).
[0417] In the compound represented by the general formula (1X), it is preferable that ma is 1 or 2, and mb is 1 or 2.
[0418] In the compound represented by the general formula (1X), it is preferable that ma is 1 and mb is 1.
[0419] In the compound represented by the general formula (1X), Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0420] In the compound represented by the general formula (1X), Ar 101 teeth, 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 benz[a]anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, or A substituted or unsubstituted fluorenyl group is preferred.
[0421] The compound represented by the general formula (1X) is also preferably represented by the following general formula (101X).
[0422] [ka]
[0423] (In the general formula (101X), R 111 and R 112 One of them is L 101 indicates the bond position with R 133 and R 134 One of them is L 101 indicates the bonding position with R 101 ~R 110 , R 121 ~R 130 , L 101 R is not a bond position with 111 or R 112 , and L 101 R is not a bond position with 133 or R 134 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, mx is 1, 2, 3, 4 or 5; L 101 If there are two or more, there are two or more L 101 are either identical or different.)
[0424] In the compound represented by the general formula (1X), L 101 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
[0425] The compound represented by the general formula (1X) is also preferably represented by the following general formula (102X).
[0426] [ka]
[0427] (In the general formula (102X), R 111 and R 112 One of them is L 111 indicates the bond position with R 133 and R 134 One of them is L 112 indicates the bonding position with R 101 ~R 110 , R 121 ~R 130 , L 111 R is not a bond position with 111 or R 112 and L 112 R is not a bond position with 133 or R 134 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X1 is a CR 143 R 144 , oxygen atom, sulfur atom, or NR 145 and L 111 and L 112 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ma is 1, 2, 3 or 4; mb is 1, 2, 3 or 4; ma+mb is 2, 3, 4 or 5, R 141 , R 142 , R 143 , R144 and R 145 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mc is 3, The Three Rs 141 are identical to or different from each other, md is 3, The Three Rs 142 are either identical or different.)
[0428] In the compound represented by the general formula (1X), it is preferable that ma in the general formula (102X) is 1 or 2, and mb is 1 or 2.
[0429] In the compound represented by the general formula (1X), it is preferable that ma in the general formula (102X) is 1 and mb is 1.
[0430] In the compound represented by the general formula (1X), the group represented by the general formula (11X) is also preferably a group represented by the following general formula (11AX) or a group represented by the following general formula (11BX).
[0431] [ka]
[0432] (In the general formula (11AX) and the general formula (11BX), R 121 ~R 131 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When a plurality of groups represented by the general formula (11AX) are present, the plurality of groups represented by the general formula (11AX) are the same or different from each other, When a plurality of groups represented by the general formula (11BX) are present, the plurality of groups represented by the general formula (11BX) are the same or different from each other, L 131 and L 132 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, * in the general formula (11AX) and the general formula (11BX) respectively indicates the bonding position to the benz[a]anthracene ring in the general formula (1X).
[0433] The compound represented by the general formula (1X) is also preferably represented by the following general formula (103X).
[0434] [ka]
[0435] (In the general formula (103X), R 101 ~R 110 and R 112 are R in the general formula (1X), respectively. 101 ~R 110 and R 112 is synonymous with R 121 ~R 131 , L 131 and L 132 are R in the general formula (11BX), respectively. 121 ~R 131 , L 131 and L 132 is equivalent to
[0436] In the compound represented by the general formula (1X), L 131is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
[0437] In the compound represented by the general formula (1X), L 132 is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
[0438] In the compound represented by the general formula (1X), R 101 ~R 112 It is also preferable that two or more of the above are groups represented by the general formula (11).
[0439] In the compound represented by the general formula (1X), R 101 ~R 112 two or more of the above are groups represented by the general formula (11X), and Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0440] In the compound represented by the general formula (1X), Ar 101 is not a substituted or unsubstituted benz[a]anthryl group, L 101 is not a substituted or unsubstituted benz[a]anthrylene group, R which is not a group represented by the general formula (11X) 101 ~R 110 It is also preferable that the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms as represented by is not a substituted or unsubstituted benz[a]anthryl group.
[0441] In the compound represented by the general formula (1X), R 101 ~R 112 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0442] In the compound represented by the general formula (1X), R 101 ~R 112 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms is preferred.
[0443] In the compound represented by the general formula (1X), R 101 ~R 112 is preferably a hydrogen atom.
[0444] A compound represented by the general formula (12X) In the organic EL device according to this embodiment, the first compound is also preferably a compound represented by the following general formula (12X).
[0445] [ka]
[0446] (In the general formula (12X), R 1201 ~R 1210 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 1201 ~R 1210 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (121), However, when the substituted or unsubstituted monocyclic ring has a substituent, the substituent when the substituted or unsubstituted fused ring has a substituent, and R 1201 ~R 1210 at least one of is a group represented by the general formula (121), When a plurality of groups represented by the general formula (121) are present, the plurality of groups represented by the general formula (121) are the same or different from each other, L 1201 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 1201 teeth, 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, mx2 is 0, 1, 2, 3, 4 or 5; L 1201 If there are two or more, there are two or more L 1201 are identical to or different from each other, Ar 1201 If there are two or more, there are two or more Ar 1201 are identical to or different from each other, In the general formula (121), * indicates the bonding position to the ring represented by the general formula (12X).
[0447] In the general formula (12X), R 1201 ~R 1210 A pair of adjacent pairs of R 1201 and R 1202 Paired with R 1202 and R 1203 Paired with R 1203 and R 1204 Paired with R 1204 and R 1205 Paired with R 1205 and R 1206 Paired with R 1207 and R 1208 Paired with R 1208 and R 1209 Pairs with and R 1209 and R 1210 It is paired with.
[0448] A compound represented by the general formula (13X) In the organic EL device according to this embodiment, the first compound is also preferably a compound represented by the following general formula (13X).
[0449] [ka]
[0450] (In the general formula (13X), R 1301 ~R 1310are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (131), However, R 1301 ~R 1310 at least one of is a group represented by the general formula (131), When a plurality of groups represented by the general formula (131) are present, the plurality of groups represented by the general formula (131) are the same or different from each other, L 1301 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 1301 teeth, 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, mx3 is 0, 1, 2, 3, 4 or 5; L 1301 If there are two or more, there are two or more L 1301 are identical to or different from each other, Ar 1301 If there are two or more, there are two or more Ar 1301 are identical to or different from each other, * in the general formula (131) indicates the bonding position to the fluoranthene ring in the general formula (13X).
[0451] In the organic EL device according to this embodiment, R 1301 ~R 1310 In the general formula (13X), the pair of adjacent two or more groups is not bonded to each other. 1301 and R 1302 Paired with R 1302 and R 1303 Paired with R 1303 and R 1304 Paired with R 1304 and R 1305 Paired with R 1305 and R 1306 Paired with R 1307 and R 1308 Paired with R 1308 and R 1309 Pairs with and R 1309 and R 1310 It is paired with.
[0452] A compound represented by the general formula (14X) In the organic EL device according to this embodiment, the first compound is also preferably a compound represented by the following general formula (14X).
[0453] [ka]
[0454] (In the general formula (14X), R 1401 ~R 1410 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (141), However, R 1401 ~R 1410 at least one of is a group represented by the general formula (141), When a plurality of groups represented by the general formula (141) are present, the plurality of groups represented by the general formula (141) are the same or different from each other, L 1401 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 1401 teeth, 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, mx4 is 0, 1, 2, 3, 4 or 5, L 1401 If there are two or more, there are two or more L 1401 are identical to or different from each other, Ar 1401 If there are two or more, there are two or more Ar 1401 are identical to or different from each other, In the general formula (141), * indicates the bonding position to the ring represented by the general formula (14X).
[0455] A compound represented by the general formula (15X) In the organic EL device according to this embodiment, the first compound is also preferably a compound represented by the following general formula (15X).
[0456] [ka]
[0457] (In the general formula (15X), R 1501 ~R 1514 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (151), However, R 1501 ~R 1514 at least one of is a group represented by the general formula (151), When a plurality of groups represented by the general formula (151) are present, the plurality of groups represented by the general formula (151) are the same or different from each other, L 1501 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 1501 teeth, 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, mx5 is 0, 1, 2, 3, 4 or 5, L 1501 If there are two or more, there are two or more L 1501 are identical to or different from each other, Ar 1501 If there are two or more, there are two or more Ar 1501 are identical to or different from each other, In the general formula (151), * indicates the bonding position to the ring represented by the general formula (15X).
[0458] A compound represented by the general formula (16X) In the organic EL device according to this embodiment, the first compound is also preferably a compound represented by the following general formula (16X).
[0459] [ka]
[0460] (In the general formula (16X), R 1601 ~R 1614 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (161), However, R 1601~R 1614 at least one of is a group represented by the general formula (161), When a plurality of groups represented by the general formula (161) are present, the plurality of groups represented by the general formula (161) are the same or different from each other, L 1601 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 1601 teeth, 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, mx6 is 0, 1, 2, 3, 4 or 5, L 1601 If there are two or more, there are two or more L 1601 are identical to or different from each other, Ar 1601 If there are two or more, there are two or more Ar 1601 are identical to or different from each other, In the general formula (161), * indicates the bonding position to the ring represented by the general formula (16X).
[0461] In the first compound and the second compound, it is preferable that the groups described as "substituted or unsubstituted" are both "unsubstituted" groups.
[0462] (Method for producing the first compound) The first compound can be produced by a known method. Alternatively, the first compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.
[0463] (Specific Examples of the First Compound) Specific examples of the first compound include the following compounds, however, the present invention is not limited to these specific examples of the first compound. In the present specification, in specific examples of compounds, D represents a deuterium atom, Me represents a methyl group, and tBu represents a tert-butyl group.
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[0556] (Second Host Material) In the organic EL device according to this embodiment, the second host material is also preferably an anthracene derivative.
[0557] In the organic EL device according to this embodiment, the second host material is also preferably a second compound represented by the following general formula (2).
[0558] [ka]
[0559] (In the general formula (2), R 201 ~R 208 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 201 and L 202 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 201 and Ar 202are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0560] (In the second compound according to this embodiment, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently, hydrogen atoms, 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, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are either identical or different.)
[0561] In the organic EL element according to this embodiment, R 201 ~R 208 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, a cyano group, or is a nitro group, L 201 and L 202 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar201 and Ar 202 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0562] In the organic EL element according to this embodiment, L 201 and L 202 are each independently, a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, Ar 201 and Ar 202 are preferably each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0563] In the organic EL element according to this embodiment, Ar 201 and Ar 202 are each independently, phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl groups, diphenylfluorenyl group, dimethylfluorenyl group, benzodiphenylfluorenyl group, benzodimethylfluorenyl group, dibenzofuranyl group, dibenzothienyl group, a naphthobenzofuranyl group, or A naphthobenzothienyl group is preferred.
[0564] In the organic EL device according to this embodiment, the second compound represented by the general formula (2) is preferably a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208), or general formula (209).
[0565] [ka]
[0566] [ka]
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[0569] [ka]
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[0571] [ka]
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[0573] [ka]
[0574] (In the general formulas (201) to (209), L 201 and Ar 201 is L in the general formula (2). 201 and Ar 201 is synonymous with R 201 ~R 208 are each independently R in the general formula (2). 201 ~R 208 is equivalent to
[0575] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228), or general formula (229).
[0576] [ka]
[0577] [ka]
[0578] [ka]
[0579] [ka]
[0580] [ka]
[0581] [ka]
[0582] [ka]
[0583] [ka]
[0584] [ka]
[0585] (In the general formula (221), the general formula (222), the general formula (223), the general formula (224), the general formula (225), the general formula (226), the general formula (227), the general formula (228) and the general formula (229), R 201 and R 203 ~R 208 are each independently R in the general formula (2). 201 and R 203 ~R 208 is synonymous with L 201 and Ar 201 respectively represent L in the general formula (2). 201 and Ar 201 is synonymous with L 203 is L in the general formula (2). 201 is synonymous with L 203 and L 201 are identical to or different from each other, Ar 203 represents Ar in the general formula (2). 201 is synonymous with Ar 203 and Ar 201 are either identical or different.)
[0586] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248), or general formula (249).
[0587] [ka]
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[0590] [ka]
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[0596] (In the general formula (241), the general formula (242), the general formula (243), the general formula (244), the general formula (245), the general formula (246), the general formula (247), the general formula (248) and the general formula (249), R 201 , R 202 and R 204 ~R 208 are each independently R in the general formula (2). 201 , R 202 and R 204 ~R 208 is synonymous with L 201 and Ar 201 respectively represent L in the general formula (2). 201 and Ar 201 is synonymous with L 203 is L in the general formula (2). 201 is synonymous with L 203 and L 201 are identical to or different from each other, Ar 203 represents Ar in the general formula (2). 201 is synonymous with Ar 203 and Ar 201 are either identical or different.)
[0597] In the second compound represented by the general formula (2), R 201 ~R 208 are each independently, hydrogen atoms, 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 -Si(R 901 )(R 902 )(R 903 ) is preferably a group represented by the formula (I).
[0598] L 101 teeth, a single bond, or an unsubstituted arylene group having 6 to 22 ring carbon atoms, Ar 101 is preferably a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.
[0599] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 is preferably a hydrogen atom in order to prevent the suppression of intermolecular interactions and the decrease in electron mobility. 201 ~R 208 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. R 201 ~R 208 When the second compound is a bulky substituent such as an alkyl group or a cycloalkyl group, the intermolecular interaction is suppressed, the electron mobility with respect to the first host material is reduced, and the relationship μe(H1)<μe(H2) in the above formula (Formula 33) may not be satisfied. When the second compound is used in the second emitting layer, satisfying the relationship μe(H1)<μe(H2) is expected to suppress a decrease in the recombination ability of holes and electrons in the first emitting layer and a decrease in luminous efficiency. The substituent may be a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ), an aralkyl group, -C(=O)R 801 a group represented by -COOR 802 The group represented by the formula (I), the halogen atom, the cyano group, and the nitro group may be bulky, and the alkyl group and the cycloalkyl group may be even more bulky. In the second compound represented by the general formula (2), R 201 ~R 208is preferably not a bulky substituent, is preferably not an alkyl group or a cycloalkyl group, and is preferably not an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ), an aralkyl group, -C(=O)R 801 a group represented by -COOR 802 It is more preferable that the aryl group is not a group represented by the formula (I), a halogen atom, a cyano group, or a nitro group.
[0600] In the organic EL element according to this embodiment, In the second compound represented by the general formula (2), R 201 ~R 208 are each independently, hydrogen atoms, 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 -Si(R 901 )(R 902 )(R 903 ) is preferably a group represented by the formula (I).
[0601] In the organic EL device according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 is preferably a hydrogen atom.
[0602] In the second compound, R 201 ~R 208 It is also preferable that the substituent in the case of "substituted or unsubstituted" does not include the above-mentioned substituents that may be bulky, particularly substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. 201 ~R 208In the case of "substituted or unsubstituted" in the above, the substituent does not include a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group, so that suppression of intermolecular interactions due to the presence of bulky substituents such as alkyl groups and cycloalkyl groups can be prevented, and a decrease in electron mobility can be prevented. Furthermore, when such a second compound is used in the second light-emitting layer, a decrease in the recombination ability of holes and electrons in the first light-emitting layer and a decrease in luminous efficiency can be suppressed.
[0603] R, a substituent of the anthracene skeleton 201 ~R 208 R is not a bulky substituent, but rather a substituent 201 ~R 208 It is more preferable that R is unsubstituted. 201 ~R 208 is not a bulky substituent, R as a non-bulky substituent 201 ~R 208 When a substituent is bonded to R, the substituent is preferably not a bulky substituent. 201 ~R 208 The substituent bonded to is preferably not an alkyl group or a cycloalkyl group, and is preferably an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, or —Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ), an aralkyl group, -C(=O)R 801 a group represented by -COOR 802 It is more preferable that the aryl group is not a group represented by the formula (I), a halogen atom, a cyano group, or a nitro group.
[0604] In the second compound, all of the groups described as "substituted or unsubstituted" are preferably "unsubstituted" groups.
[0605] In the organic EL device according to this embodiment, for example, Ar 201 is a substituted or unsubstituted dibenzofuranyl group.
[0606] In the organic EL device according to this embodiment, for example, Ar 201 is an unsubstituted dibenzofuranyl group.
[0607] In the organic EL device according to this embodiment, for example, the second compound represented by the general formula (2) has at least one hydrogen atom, and at least one of the hydrogen atoms is deuterium.
[0608] In the organic EL device according to this embodiment, for example, L in the second compound represented by the general formula (2) 201 is TEMP-63 or TEMP-68.
[0609] [ka]
[0610] In the organic EL device according to this embodiment, for example, Ar 201 represents a substituted or unsubstituted anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluoranthenyl group, a benzofluoranthenyl group, and and at least one group selected from the group consisting of perylenyl groups.
[0611] In the organic EL device according to this embodiment, for example, Ar 201 is a substituted or unsubstituted fluorenyl group.
[0612] In the organic EL device according to this embodiment, for example, Ar 201 is a substituted or unsubstituted xanthenyl group.
[0613] In the organic EL device according to this embodiment, for example, Ar 201 is a benzoxanthenyl group.
[0614] (Method for producing the second compound) The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.
[0615] (Specific Example of the Second Compound) Specific examples of the second compound include the following compounds, however, the present invention is not limited to these specific examples of the second compound.
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[0659] (First luminescent compound, second luminescent compound, and third luminescent compound) In the organic EL device according to this embodiment, examples of the first light-emitting compound, the second light-emitting compound, and the third light-emitting compound include the following third compound and the following fourth compound. The third compound and the fourth compound are each independently one or more compounds selected from the group consisting of a compound represented by the following general formula (3), a compound represented by the following general formula (4), a compound represented by the following general formula (5), a compound represented by the following general formula (6), a compound represented by the following general formula (7), a compound represented by the following general formula (8), a compound represented by the following general formula (9), and a compound represented by the following general formula (10).
[0660] (Compound represented by general formula (3)) The compound represented by general formula (3) will be explained.
[0661] [ka]
[0662] (In the general formula (3), R 301 ~R 310 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 301 ~R 310 At least one of the groups is a monovalent group represented by the following general formula (31): R does not form the monocyclic ring, does not form the fused ring, and is not a monovalent group represented by the following general formula (31): 301 ~R 310 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0663] [ka]
[0664] (In the general formula (31), Ar 301 and Ar 302 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, L 301 ~L 303 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, * indicates the bonding position on the pyrene ring in the general formula (3).
[0665] In the third compound and the fourth compound, R 901 , R 902 , R 903 , R 904 , R 905 , R906 and R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other.
[0666] In the general formula (3), R 301 ~R 310 It is preferable that two of them are groups represented by the general formula (31).
[0667] In one embodiment, the compound represented by the general formula (3) is a compound represented by the following general formula (33).
[0668] [ka]
[0669] (In the general formula (33), R 311 ~R 318 are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). 301 ~R 310 is synonymous with L 311 ~L 316 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, Ar 312 , Ar 313 , Ar 315 and Ar 316 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0670] In the general formula (31), L 301 is preferably a single bond, and L 302 and L 303 is preferably a single bond.
[0671] In one embodiment, the compound represented by the general formula (3) is represented by the following general formula (34) or (35).
[0672] [ka]
[0673] (In the general formula (34), R 311 ~R318 are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). 301 ~R 310 is synonymous with L 312 , L 313 , L 315 and L 316 each independently represents L in the general formula (33). 312 , L 313 , L 315 and L 316 is synonymous with Ar 312 , Ar 313 , Ar 315 and Ar 316 are each independently the Ar in the general formula (33). 312 , Ar 313 , Ar 315 and Ar 316 is equivalent to
[0674] [ka]
[0675] (In the general formula (35), R 311 ~R 318 are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). 301 ~R 310 is synonymous with Ar 312 , Ar 313 , Ar 315 and Ar 316 are each independently the Ar in the general formula (33). 312 , Ar 313 , Ar 315 and Ar 316 is equivalent to
[0676] In the general formula (31), preferably, Ar 301 and Ar 302 At least one of the above is a group represented by the following general formula (36). In the general formulas (33) to (35), preferably, Ar 312 and Ar 313 At least one of the above is a group represented by the following general formula (36). In the general formulas (33) to (35), preferably, Ar 315 and Ar 316 At least one of the above is a group represented by the following general formula (36).
[0677] [ka]
[0678] (In the general formula (36), X3 represents an oxygen atom or a sulfur atom; R 321 ~R 327 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 321 ~R 327 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, *L 302 , L 303 , L 312 , L 313 , L 315 or L 316 )
[0679] X3 is preferably an oxygen atom.
[0680] R 321 ~R 327 At least one of the 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0681] In the general formula (31), Ar 301 is a group represented by the general formula (36), and Ar 302 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. In the general formulas (33) to (35), Ar 312 is a group represented by the general formula (36), and Ar 313 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. In the general formulas (33) to (35), Ar 315 is a group represented by the general formula (36), and Ar 316is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
[0682] In one embodiment, the compound represented by the general formula (3) is represented by the following general formula (37).
[0683] [ka]
[0684] (In the general formula (37), R 311 ~R 318 are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). 301 ~R 310 is synonymous with R 321 ~R 327 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 341 ~R 347 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 321 ~R 327 and R 341 ~R 347 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 331 ~R 335 and R 351 ~R 355 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0685] Specific examples of the compound represented by the general formula (3) include the compounds shown below.
[0686] [ka]
[0687] [ka]
[0688] [ka]
[0689] [ka]
[0690] [ka]
[0691] (Compound represented by general formula (4)) The compound represented by general formula (4) will be explained.
[0692] [ka]
[0693] (In the general formula (4), Each Z is independently CRa or a nitrogen atom; Ring A1 and ring A2 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, When there are a plurality of Ra, one or more pairs of adjacent two or more of the plurality of Ra are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, n21 and n22 each independently represent 0, 1, 2, 3, or 4; When a plurality of Rb's are present, one or more pairs of adjacent two or more Rb's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When there are a plurality of Rc's, one or more pairs of adjacent two or more Rc's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ra, Rb, and Rc that do not form a single ring and do not form a fused ring each independently represent: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0694] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring A1 and ring A2 contains, as ring-forming atoms, two carbon atoms on the central fused two-ring structure of general formula (4). Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1.
[0695] The "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group." The "heterocycle" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of general formula (4) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.
[0696] Rb is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A1, or any of the atoms forming the heterocycle as ring A1.
[0697] Rc is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A2, or any of the atoms forming the heterocycle as ring A2.
[0698] At least one of Ra, Rb, and Rc is preferably a group represented by the following general formula (4a), and more preferably at least two of them are groups represented by the following general formula (4a).
[0699] [ka]
[0700] (In the general formula (4a), L 401 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, Ar 401 teeth, 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 It is a group represented by the following general formula (4b):
[0701] [ka]
[0702] (In the general formula (4b), L 402 and L 403 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, Ar 402 and Ar 403 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ar does not form the single ring and does not form the fused ring 402 and Ar 403 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0703] In one embodiment, the compound represented by the general formula (4) is represented by the following general formula (42).
[0704] [ka]
[0705] (In the general formula (42), R 401 ~R 411 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 401 ~R 411 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0706] R 401 ~R 411Among these, at least one is preferably a group represented by the general formula (4a), and more preferably at least two are groups represented by the general formula (4a). R 404 and R 411 is preferably a group represented by the general formula (4a).
[0707] In one embodiment, the compound represented by the general formula (4) is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bonded to the A1 ring. In one embodiment, the compound represented by the general formula (42) is R 404 ~R 407 is a compound in which a structure represented by the following general formula (4-1) or general formula (4-2) is bonded to the ring to which
[0708] [ka]
[0709] (In the general formula (4-1), two * are each independently bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle as the A1 ring in the general formula (4), or to a ring-forming atom of R in the general formula (42). 404 ~R 407 combines with either The three * in the general formula (4-2) each independently bond to a ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle as the A1 ring in the general formula (4), or bond to R in the general formula (42). 404 ~R 407 combines with either R 421 ~R 427 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 431 ~R 438One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 421 ~R 427 and R 431 ~R 438 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0710] In one embodiment, the compound represented by the general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4), or general formula (41-5).
[0711] [ka]
[0712] [ka]
[0713] [ka]
[0714] (In the general formula (41-3), formula (41-4) and formula (41-5), Ring A1 is as defined in general formula (4), R 421 ~R 427 are each independently R in the general formula (4-1). 421 ~R 427 is synonymous with R 440 ~R 448 are each independently R in the general formula (42). 401 ~R 411 is equivalent to
[0715] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms as ring A1 in general formula (41-5) is a substituted or unsubstituted naphthalene ring, or It is a substituted or unsubstituted fluorene ring.
[0716] In one embodiment, the substituted or unsubstituted heterocycle having 5 to 50 ring atoms as ring A1 in general formula (41-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or It is a substituted or unsubstituted dibenzothiophene ring.
[0717] In one embodiment, the compound represented by the general formula (4) or the general formula (42) is selected from the group consisting of compounds represented by the following general formulas (461) to (467).
[0718] [ka]
[0719] [ka]
[0720] [ka]
[0721] [ka]
[0722] [ka]
[0723] (In the general formula (461), the general formula (462), the general formula (463), the general formula (464), the general formula (465), the general formula (466) and the general formula (467), R 421 ~R 427 are each independently R in the general formula (4-1). 421 ~R 427 is synonymous with R 431 ~R 438 are each independently R in the general formula (4-2). 431 ~R 438 is synonymous with R 440 ~R 448 and R 451 ~R 454 are each independently R in the general formula (42). 401 ~R 411 is synonymous with X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ) and R 801 , R 802 and R 803are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, R 803 If there are multiple R 803 are either identical or different.)
[0724] In one embodiment, the compound represented by general formula (42) is R 401 ~R 411 one or more pairs of adjacent two or more of these bond to each other to form a substituted or unsubstituted monocycle, or bond to each other to form a substituted or unsubstituted fused ring, and this embodiment will be described in detail below as a compound represented by general formula (45).
[0725] (Compound represented by general formula (45)) The compound represented by general formula (45) will be explained.
[0726] [ka]
[0727] (In the general formula (45), R 461 and R 462 A set consisting of462 and R 463 A set consisting of 464 and R 465 A set consisting of 465 and R 466 A set consisting of 466 and R 467 A set consisting of 468 and R 469 A set consisting of 469 and R 470 and R 470 and R 471 two or more of the pairs selected from the group consisting of pairs of however, R 461 and R 462 and R 462 and R 463 A set consisting of and; R 464 and R 465 and R 465 and R 466 A set consisting of and; R 465 and R 466 and R 466 and R 467 A set consisting of and; R 468 and R 469 and R 469 and R 470 and R 469 and R 470 and R 470 and R 471 and do not simultaneously form a ring, R 461 ~R 471 The two or more rings formed by are the same or different, R does not form the monocyclic ring and does not form the fused ring 461 ~R 471 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ), -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0728] In the general formula (45), R n and R n+1 (n represents an integer selected from 461, 462, 464 to 466, and 468 to 470) are bonded to each other to form R n and R n+1 is bonded to the two ring-forming carbon atoms to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from the group consisting of carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, and more preferably 5 or 6.
[0729] The number of the ring structures in the compound represented by the general formula (45) is, for example, two, three, or four. The two or more ring structures may be present on the same benzene ring on the parent skeleton of the general formula (45), or may be present on different benzene rings. For example, when the compound has three ring structures, one ring structure may be present on each of the three benzene rings in the general formula (45).
[0730] Examples of the ring structure in the compound represented by the general formula (45) include structures represented by the following general formulae (451) to (460).
[0731] [ka]
[0732] (In the general formulae (451) to (457), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 are R n and R n+1 represents the two ring-forming carbon atoms to which are bonded, R n The ring-forming carbon atom to which is bonded may be either of the two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14, X 45 is C(R 4512 )(R 4513 ), NR 4514 , an oxygen atom or a sulfur atom, R 4501 ~R 4506 and R 4512 ~R 4513 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 4501 ~R 4514 are each independently R in the general formula (45). 461 ~R 471 is equivalent to
[0733] [ka]
[0734] (In the general formulae (458) to (460), *1 and *2, and *3 and *4 are R n and R n+1 represents the two ring-forming carbon atoms to which are bonded, R n The ring carbon atom to which is bonded may be either the two ring carbon atoms represented by *1 and *2, or *3 and *4, X 45 is C(R 4512 )(R 4513 ), NR 4514 , an oxygen atom or a sulfur atom, R 4512 ~R 4513 and R 4515 ~~R 4525 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 4512 ~R 4513 , R 4515 ~R 4521 and R 4522 ~R 4525 , and R 4514 are each independently R in the general formula (45). 461 ~R 471 is equivalent to
[0735] In the general formula (45), R 462 , R 464 , R 465 , R 470 and R 471 at least one of (preferably R 462 , R 465 and R 470 and more preferably at least one of R 462 ) is preferably a group that does not form a ring structure.
[0736] (i) In the general formula (45), Rn and R n+1 a substituent when the ring structure formed by the formula (I) has a substituent, (ii) In the general formula (45), R 461 ~R 471 , and (iii) R in equations (451) to (460) 4501 ~R 4514 , R 4515 ~~R 4525 are preferably each independently hydrogen atoms, 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, -N(R 906 )(R 907 ) a group represented by 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 It is any one of groups selected from the group consisting of groups represented by the following general formulae (461) to (464).
[0737] [ka]
[0738] (In the general formulas (461) to (464), R d are each independently, hydrogen atoms, 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, -Si(R 901 )(R902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, X 46 is C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom, R 801 , R 802 and R 803 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, R 803 If there are multiple R 803 are the same or different from each other, p1 is 5, p2 is 4, p3 is 3, p4 is 7, In the general formulae (461) to (464), * each independently indicates the bonding position to the ring structure. In the third compound and the fourth compound, R 901 ~R 907 is as defined above.
[0739] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-1) to (45-6).
[0740] [ka]
[0741] [ka]
[0742] (In the general formulae (45-1) to (45-6), rings d to i each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; R 461 ~R 471 are each independently R in the general formula (45). 461 ~R 471 is equivalent to
[0743] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-7) to (45-12).
[0744] [ka]
[0745] [ka]
[0746] (In the general formulae (45-7) to (45-12), rings d to f, k, and j each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; R 461 ~R 471 are each independently R in the general formula (45). 461 ~R 471 is equivalent to
[0747] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-13) to (45-21).
[0748] [ka]
[0749] [ka]
[0750] [ka]
[0751] (In the general formulae (45-13) to (45-21), rings d to k each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; R 461 ~R 471 are each independently R in the general formula (45). 461 ~R 471 is equivalent to
[0752] When the ring g or the ring h further has a substituent, examples of the substituent include: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; A group represented by the general formula (461), A group represented by the general formula (463), or Examples include the group represented by the general formula (464).
[0753] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-22) to (45-25).
[0754] [ka]
[0755] (In the general formulae (45-22) to (45-25), X 46 and X 47 are each independently C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom, R 461 ~R 471 and R 481 ~R 488 are each independently R in the general formula (45). 461 ~R 471 is synonymous with. R 801 , R 802 and R 803 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 801 If there are multiple R 801 are the same or different from each other, R 802If there are multiple R 802 are the same or different from each other, R 803 If there are multiple R 803 are either identical or different.)
[0756] In one embodiment, the compound represented by the general formula (45) is represented by the following general formula (45-26):
[0757] [ka]
[0758] (In the general formula (45-26), X 46 is C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom, R 463 , R 464 , R 467 , R 468 , R 471 , and R 481 ~R 492 are each independently R in the general formula (45). 461 ~R 471 is synonymous with. R 801 , R 802 and R 803 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 801 If there are multiple R801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, R 803 If there are multiple R 803 are either identical or different.)
[0759] Specific examples of the compound represented by the general formula (4) include the compounds shown below: In the specific examples below, Ph represents a phenyl group, and D represents a deuterium atom.
[0760] [ka]
[0761] [ka]
[0762] [ka]
[0763] [ka]
[0764] [ka]
[0765] [ka]
[0766] [ka]
[0767] [ka]
[0768] [ka]
[0769] [ka]
[0770] (Compound represented by general formula (5)) The compound represented by general formula (5) will be explained below: The compound represented by general formula (5) corresponds to the compound represented by general formula (41-3) described above.
[0771] [ka]
[0772] (In the general formula (5), R 501 ~R 507 and R 511 ~R 517 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 501 ~R 507 and R 511 ~R 517 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 521 and R 522 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0773] "R 501 ~R 507 and R 511 ~R517 "A set of two or more adjacent pairs of R" is, for example, 501 and R 502 A set consisting of R 502 and R 503 A set consisting of R 503 and R 504 A set consisting of R 505 and R 506 A set consisting of R 506 and R 507 A set consisting of R 501 and R 502 and R 503 It is a combination of a set consisting of:
[0774] In one embodiment, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two of the following are -N(R 906 )(R 907 ) is a group represented by the formula:
[0775] In one embodiment, R 501 ~R 507 and R 511 ~R 517 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0776] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52):
[0777] [ka]
[0778] (In the general formula (52), R 531 ~R 534 and R 541 ~R 544 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 531 ~R 534 , R 541 ~R 544 , and R 551 and R 552 are each independently, hydrogen 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, R 561 ~R 564 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0779] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (53):
[0780] [ka]
[0781] (In the general formula (53), R 551 , R 552 and R 561 ~R 564 are each independently R in the general formula (52). 551 , R 552 and R 561 ~R 564 is equivalent to
[0782] In one embodiment, R in the general formula (52) and the general formula (53) 561 ~R 564are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).
[0783] In one embodiment, R in general formula (5) 521 and R 522 R in the general formula (52) and the general formula (53) 551 and R 552 is a hydrogen atom.
[0784] In one embodiment, the substituent in the case of “substituted or unsubstituted” in the general formula (5), the general formula (52), and the general formula (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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0785] Specific examples of the compound represented by the general formula (5) include the compounds shown below.
[0786] [ka]
[0787] [ka]
[0788] [ka]
[0789] [ka]
[0790]
change
[0791]
change
[0792]
change
[0793]
change
[0794]
change
[0795]
change
[0796]
change
[0797]
change
[0798]
change
[0799]
change
[0800] [ka]
[0801] [ka]
[0802] [ka]
[0803] (Compound represented by general formula (6)) The compound represented by general formula (6) will be explained.
[0804] [ka]
[0805] (In the general formula (6), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, R 601 and R 602 each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601 and R 602 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0806] The rings a, b, and c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms) fused to the central fused bicyclic structure of the general formula (6) composed of a boron atom and two nitrogen atoms.
[0807] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of the general formula (6) as ring-forming atoms. The "aromatic hydrocarbon ring" of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of general formula (6) as ring-forming atoms.
[0808] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1. The "heterocycles" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group." The "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "heterocycle" of rings b and c contains two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. Specific examples of "substituted or unsubstituted heterocycles having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.
[0809] R 601 and R 602 may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring contains the nitrogen atom on the central fused bicyclic structure of the general formula (6). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. R 601 and R 602is bonded to ring a, ring b, or ring c specifically means that an atom constituting ring a, ring b, or ring c is bonded to R 601 and R 602 It means that the atoms that make up R are bonded together. 601 is bonded to the a ring, and R 601 and ring a may be fused to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. R 601 When is bonded to ring b, R 602 When R is bonded to ring a, 602 The same applies when is bonded to ring c.
[0810] In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
[0811] In one embodiment, R in general formula (6) 601 and R 602 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, A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms is preferred.
[0812] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62):
[0813] [ka]
[0814] (In the general formula (62), R 601A is R 611 and R 621 to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R 602A is R 613 and R 614 to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601A and R 602A are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 611 ~R 621 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, the monocyclic ring, or the fused ring. 611 ~R 621 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0815] R in the general formula (62) 601A and R 602A are R in the general formula (6), respectively. 601 and R 602 is a group corresponding to For example, R 601A and R 611 may be bonded to form a two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring in which a ring containing the ring is fused with a benzene ring corresponding to ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. 601A and R 621 If R 602A and R 613 When R is bonded, 602A and R 614 The same applies when the two are combined.
[0816] R 611 ~R 621 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or They may be bonded to each other to form a substituted or unsubstituted fused ring. For example, R 611 and R 612may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused to the six-membered ring to which they are bonded, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.
[0817] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0818] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0819] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, a hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0820] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0821] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (63):
[0822] [ka]
[0823] (In the general formula (63), R 631 is R 646 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 633 is R 647 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 634 is R 651 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 641 is R 642 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 631 ~R 651 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, the monocyclic ring, or the fused ring. 631 ~R 651 are each independently, hydrogen atoms, 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0824] R 631 is R 646 may be bonded to form a substituted or unsubstituted heterocycle. For example, R 631 and R 646 are combined to form R 646 The benzene ring to which R is bonded, the ring containing N, and the benzene ring corresponding to ring a may be condensed to form a nitrogen-containing heterocyclic ring having three or more condensed rings. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more condensed rings in the specific example group G2. 633 and R 647 If R 634 and R 651 When R is bonded, 641 and R 642 The same applies when the two are combined.
[0825] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0826] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
[0827] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, a hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0828] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
[0829] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63A):
[0830] [ka]
[0831] (In the general formula (...
Claims
1. A tandem organic electroluminescent element, comprising: an anode; A cathode; two or more light-emitting units disposed between the anode and the cathode; a first cathode-side organic layer disposed between the anode and the cathode; At least one of the two or more light-emitting units is a stacked light-emitting unit; the first cathode-side organic layer is disposed on the cathode side of at least one of the stacked light-emitting units; the first cathode-side organic layer contains a phenanthroline compound having a phenanthroline skeleton and an electron-donating material, The phenanthroline compound contained in the first cathode-side organic layer has one group represented by the following general formula (21) and is a compound represented by the following general formula (20): the stacked light-emitting unit includes a first light-emitting layer and a second light-emitting layer; the first light-emitting layer contains a first host material and a first light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less; the second light-emitting layer contains a second host material and a second light-emitting compound that emits light having a maximum peak wavelength of 500 nm or less, The first host material has, in a molecule, a structure satisfying the following condition (i) or a structure satisfying the following condition (ii): the second host material is an anthracene derivative, the first host material and the second host material are different from each other; the first luminescent compound and the second luminescent compound are the same or different from each other; a second cathode-side organic layer containing no phenanthroline compound having a phenanthroline skeleton is disposed between the first light-emitting layer and the first cathode-side organic layer; the second cathode-side organic layer contains an azine derivative; Organic electroluminescent element. Condition (i) The compound has a biphenyl structure in which a first benzene ring and a second benzene ring are connected by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further connected by a bridge at at least one portion other than the single bond. Condition (ii) has a linking structure including a benzene ring and a naphthalene ring linked by a single bond, The benzene ring and the naphthalene ring in the linking structure are each independently fused or not fused with a single ring or a fused ring, and the benzene ring and the naphthalene ring in the linking structure are further linked to each other in at least one portion other than the single bond by a bridge formed by a single bond, a bridge containing a double bond, or a bridge containing a hetero atom. 【Transformation 3】 (In the general formula (20), X 21 to X 28 each independently represent a carbon atom bonded to CR 21 or the group represented by general formula (21); one of X 21 to X 28 is a carbon atom bonded to the group represented by the general formula (21); adjacent pairs of two or more R 21 's are not bonded to each other; R 21 independently represents: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a cyano group, or It is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. (In the general formula (21), Ar 2 is 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, p is 1, L 2 is a single bond or a linking group; L 2 as a linking group is a substituted or unsubstituted polyvalent aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a polyvalent multiple linking group formed by bonding two groups selected from the polyvalent aromatic hydrocarbon groups, the aromatic hydrocarbon groups constituting L 2 as the multiple linking group are the same or different, and adjacent groups are not bonded to each other; Ar 2 and L 2 as a linking group are not bonded to each other; L 2 as a linking group and any carbon atom of X 21 to X 28 adjacent to the carbon atom bonded to L 2 or R 21 of CR 21 are not bonded to each other; In the compound represented by the general formula (20), the substituent in the case of being "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 18 ring carbon atoms, In the general formula (21), * indicates the bonding position to the ring represented by the general formula (20).
2. the first light-emitting layer, the second light-emitting layer, the second cathode-side organic layer, and the first cathode-side organic layer are arranged in this order from the anode side; The organic electroluminescence device according to claim 1 .
3. the first light-emitting layer of the stacked light-emitting unit is disposed between the second light-emitting layer and the first cathode-side organic layer; The organic electroluminescence device according to claim 1 .
4. The organic electroluminescent device according to any one of claims 1 to 3, the first host material has a structure satisfying the condition (i) in its molecule, the first benzene ring and the second benzene ring in the biphenyl structure are further linked by the bridge at one site other than the single bond; Organic electroluminescent element.
5. The organic electroluminescent device according to any one of claims 1 to 3, the first host material has a structure satisfying the condition (i) in its molecule, the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the bridge at two portions other than the single bond; Organic electroluminescent element.
6. The organic electroluminescent device according to any one of claims 1 to 5, the bridge comprises a double bond; Organic electroluminescent element.
7. The organic electroluminescent device according to any one of claims 1 to 3, The first host material has at least one group represented by the following general formula (11) and is a first compound represented by the following general formula (1): Organic electroluminescent element. 【Chemistry 1】 (In the general formula (1), R 101 ~R 110 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or A group represented by the general formula (11), However, R 101 ~R 110 At least one of the groups is a group represented by the general formula (11), When a plurality of groups represented by the general formula (11) are present, the plurality of groups represented by the general formula (11) are the same or different from each other, L 101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx is 0, 1, 2, 3, 4 or 5; L 101 When there are two or more, there are two or more L 101 are identical to or different from each other, Ar 101 When two or more are present, two or more Ar 101 are identical to or different from each other, * in the general formula (11) indicates the bonding position to the pyrene ring in the general formula (1). (In the first compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently, hydrogen atoms, 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, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, In the first compound, the substituent in the case of being "substituted or unsubstituted" 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.
8. The organic electroluminescent device according to any one of claims 1 to 3, the first host material has a structure satisfying the condition (i) in its molecule, the first benzene ring and the second benzene ring in the biphenyl structure are further connected by the bridge at two portions other than the single bond, the crosslink does not contain a double bond; Organic electroluminescent element.
9. The organic electroluminescent device according to any one of claims 1 to 3, the first host material has a structure that satisfies the condition (ii) in its molecule; Organic electroluminescent element.
10. The organic electroluminescence device according to claim 9, the bridge comprises a double bond; Organic electroluminescent element.
11. The organic electroluminescence element according to any one of claims 1 to 10, R 21 independently represents: hydrogen atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms; a cyano group, or an unsubstituted aryl group having 6 to 18 ring carbon atoms; Organic electroluminescent element.
12. The organic electroluminescent element according to any one of claims 1 to 10, Ar 2 is an unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, When Ar 2 is a substituted heterocyclic group, the substituted heterocyclic group Ar 2 has an aryl group having 6 to 18 ring carbon atoms as a substituent. Organic electroluminescent element.
13. The organic electroluminescent element according to any one of claims 1 to 10, L 2 as a linking group is an unsubstituted polyvalent aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a polyvalent multiple linking group formed by bonding two groups selected from the polyvalent aromatic hydrocarbon groups; Organic electroluminescent element.
14. The organic electroluminescent element according to any one of claims 1 to 10, R 21 independently represents: hydrogen atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms; a cyano group, or an unsubstituted aryl group having 6 to 18 ring carbon atoms, Ar 2 is an unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, When Ar 2 is a substituted heterocyclic group, the substituted heterocyclic group Ar 2 has an aryl group having 6 to 18 ring carbon atoms as a substituent; L 2 as a linking group is an unsubstituted polyvalent aromatic hydrocarbon group having 6 to 18 ring carbon atoms, or a polyvalent multiple linking group formed by bonding two groups selected from the polyvalent aromatic hydrocarbon groups; Organic electroluminescent element.
15. The organic electroluminescent device according to any one of claims 1 to 14, The second host material is a second compound represented by the following general formula (2): Organic electroluminescent element. 【Chemistry 2】 (In the general formula (2), R 201 ~R 208 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 ) (R 902 ) (R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 ) (R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 201 and L 202 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, Ar 201 and Ar 202 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. (In the second compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 are each independently, hydrogen atoms, 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, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, In the second compound, the substituent in the case of being "substituted or unsubstituted" 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.
16. The organic electroluminescent element according to claim 15, R 201 to R 208 each independently represent: hydrogen atoms, 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, L 201 and L 202 each independently represent: single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 18 ring atoms, Ar 201 and Ar 202 each independently represent: 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; Organic electroluminescent element.
17. the total content of the second host material and the second light-emitting compound contained in the second light-emitting layer is 100% by mass; The organic electroluminescence device according to claim 1 .
18. the second emitting layer contains a second compound as the second host material in an amount of 95 mass% or more of the total mass of the second emitting layer; The organic electroluminescence device according to claim 1 .
19. the second light-emitting layer contains only one type of the second host material or two or more types of the second host material; The organic electroluminescence device according to claim 1 .
20. the second light-emitting layer contains only one type of the second light-emitting compound or two or more types of the second light-emitting compound; The organic electroluminescence device according to claim 1 .
21. the first light-emitting layer and the first cathode-side organic layer are spaced apart by 30 nm or more; The organic electroluminescence device according to any one of claims 1 to 20.
22. the two or more light-emitting units include the stacked light-emitting unit and at least one phosphorescent light-emitting unit different from the stacked light-emitting unit; The phosphorescent light-emitting unit contains a phosphorescent compound that exhibits phosphorescent emission. The organic electroluminescence device according to any one of claims 1 to 21.
23. the first cathode-side organic layer is disposed between the stacked light-emitting unit and another light-emitting unit different from the stacked light-emitting unit; The organic electroluminescence device according to any one of claims 1 to 22.
24. the stacked light-emitting unit is disposed on the anode side of the first cathode-side organic layer; 24. The organic electroluminescence device according to claim 23.
25. The hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material satisfy the relationship of the following formula (Formula 31): The organic electroluminescence device according to any one of claims 1 to 24. μh(H1)>μh(H2)…(Math. 31)
26. The hole mobility μh(H1) of the first host material, the electron mobility μe(H1) of the first host material, the hole mobility μh(H2) of the second host material, and the electron mobility μe(H2) of the second host material satisfy the relationship of the following formula (Formula 32): The organic electroluminescence device according to any one of claims 1 to 25. (μe(H1) / μh(H1))<(μe(H2) / μh(H2))…(Math. 32)
27. The electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the relationship of the following formula (Formula 33): The organic electroluminescence device according to any one of claims 1 to 26. μe(H1)<μe(H2)…(Math. 33)
28. 28. The organic electroluminescence device according to claim 1, a color conversion unit disposed on the light extraction side of the organic electroluminescence element; Organic electroluminescent element.
29. The organic electroluminescent element according to claim 1, The singlet energy S 1 (H1) of the first host material and the singlet energy S 1 (D1) of the first light-emitting compound satisfy the relationship of the following mathematical formula (Mathematical Formula 20): Organic electroluminescent element. S 1 (H1)>S 1 (D1)...(Math. 20) 30. The organic electroluminescent element according to claim 1, The triplet energy T 1 (H1) of the first host material and the triplet energy T 1 (D1) of the first light-emitting compound satisfy the relationship of the following mathematical formula (Mathematical Formula 20A): Organic electroluminescent element. T 1 (D1)>T 1 (H1) (Equation 20A) 31. The organic electroluminescent element according to claim 1, The singlet energy S 1 (H2) of the second host material and the singlet energy S 1 (D2) of the second light-emitting compound satisfy the relationship of the following mathematical formula (Mathematical Formula 4): Organic electroluminescent element. S 1 (H2)>S 1 (D2)...(Math. 4) 32. The organic electroluminescent element according to claim 1, wherein The triplet energy T 1 (D2) of the second light-emitting compound and the triplet energy T 1 (H2) of the second host material satisfy the relationship of the following mathematical formula (Mathematical Formula 3A): Organic electroluminescent element. T 1 (D2)>T 1 (H2)...(Math. 3A)
33. 33. The organic electroluminescence device according to claim 1, which is used in a display for a television, a personal computer, a tablet, or a mobile device.
34. An electronic device equipped with the organic electroluminescence element according to any one of claims 1 to 33.
35. 35. The electronic device of claim 34, which is a television, a personal computer, a tablet, or a mobile display.
Citation Information
Patent Citations
Organic electroluminescent element
JP2007294261A
Organic light emitting element
JP2013157552A
Light-emitting element and display device
JP2013207167A
Organic el element and display device
JP2016111134A
Organic electroluminescent element, electronic device, and material for organic electroluminescent element
JP2018125504A