Compound, light-emitting element material, organic electroluminescent element, and electronic device

Abstract

To provide a compound capable of causing an organic electroluminescent element to emit light with high efficiency and a long lifetime.SOLUTION: The compound has a structure represented by general formula (1), with the proviso that each of R101 to R121 is not a substituted or unsubstituted N-carbazolyl group, the structure represented by general formula (1) does not have a group represented by general formula (12), and at least one of R101 to R121 is a group represented by general formula (13).SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a compound, a light-emitting element material, an organic electroluminescence element, and an electronic device. [Background technology]

[0002] When a voltage is applied to an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic EL devices that utilize light emission from singlet excitons are increasingly being applied to full-color displays such as those for mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, efforts are being made to improve the performance of organic EL devices. Examples of the performance of organic EL devices include brightness, emission wavelength, half-width, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0003] For example, it is expected that organic EL devices will emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. Against this background, highly efficient fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being studied. The TADF (Thermally Activated Delayed Fluorescence) mechanism utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet levels is used. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors," edited by Adachi Chinaya, Kodansha, April 1, 2012, pp. 261-268. Known compounds that exhibit thermally activated delayed fluorescence (TADF) include compounds in which a donor moiety and an acceptor moiety are bonded within the molecule.

[0004] For example, Patent Document 1 can be mentioned as a document relating to organic EL devices and compounds used in organic EL devices. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2021 / 215446 Summary of the Invention [Problem to be solved by the invention]

[0006] Further improvements in performance are required for organic EL elements utilizing the TADF mechanism. An object of the present invention is to provide a compound that enables an organic electroluminescent element to emit light with high efficiency and long lifetime, a light-emitting element material containing the compound, an organic electroluminescent element that emits light with high efficiency and long lifetime, and an electronic device equipped with the organic EL element. [Means for solving the problem]

[0007] According to one aspect of the present invention, there is provided a compound having a structure represented by general formula (1).

[0008] [ka]

[0009] (In the general formula (1), R 101 ~R 121 are each independently hydrogen atoms, halogen 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R 190 ) a group represented by -S-(R 191 ) 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, -C(=O)-O-(R 192 ) a group represented by -C(=O)-N(R 193 )(R 194 ) a group represented by -N(R 195 )(R 196 ) a group represented by nitro group, -Si(R 197 )(R 198 )(R 199 ) a group represented by selected from the group consisting of groups represented by the following general formula (13): R 101 ~R 121 At least one of the groups is a group represented by the following general formula (13): (In the compound having the structure represented by the general formula (1), R 190 ~R 199 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. However, R 101 ~R 121is not a substituted or unsubstituted N-carbazolyl group, The structure represented by the general formula (1) does not have a group represented by the following general formula (12):

[0010] [ka]

[0011] (In the group represented by the general formula (12), X 1 is a nitrogen atom or CR 141 represents X 2 is a nitrogen atom or CR 142 represents X 3 is a nitrogen atom or CR 143 represents X 4 is a nitrogen atom or CR 144 represents X 5 is a nitrogen atom or CR 145 represents R 141 ~R 145 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. However, X 1 ~X 5 At least one of these is represented by a nitrogen atom. * indicates the bond position.

[0012] [ka]

[0013] (In the group represented by the general formula (13), Y is a nitrogen atom or CR 135 represents R 131 ~R 134 one or more pairs of adjacent two or more of R 135 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 131 ~R 134 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; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -L 1 -R 136 is a group represented by L 1 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, R 136 teeth, 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, * indicates the bond position.

[0014] According to one aspect of the present invention, there is provided a light-emitting device material including a compound according to one aspect of the present invention.

[0015] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including one or more layers, at least one of which contains a compound according to one aspect of the present invention as a first compound.

[0016] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention. [Effects of the Invention]

[0017] According to one aspect of the present invention, it is possible to provide a compound that can cause an organic electroluminescence device to emit light with high efficiency and a long lifetime, a light-emitting element material containing the compound, an organic electroluminescence device that emits light with high efficiency and a long lifetime, and an electronic device equipped with the organic EL device. [Brief explanation of the drawings]

[0018] [Figure 1] FIG. 10 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Figure 2] FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Figure 3] FIG. 10 is a diagram showing an example of an attenuation curve of a transient PL. [Figure 4] FIG. 10 is a diagram showing the energy levels of a first compound and a second compound in an emitting layer of an example of an organic electroluminescence element according to a third embodiment of the present invention, and the relationship between energy transfer. [Figure 5] FIG. 10 is a diagram showing the energy levels of a first compound, a second compound, and a third compound in an example of an emitting layer of an organic electroluminescence element according to a fourth embodiment of the present invention, as well as the relationship between energy transfer. DETAILED DESCRIPTION OF THE INVENTION

[0019] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0020] 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.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] "Substituents described herein" The substituents described in this specification will be explained below.

[0027] 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.

[0028] "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.

[0029] 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).

[0030] [ka]

[0031] [ka]

[0032] 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.

[0033] "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.

[0034] 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).

[0035] 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).

[0036] 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, an azacarbazolyl group, and Diazacarbazolyl group.

[0037] 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.

[0038] 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).

[0039] 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):

[0040] [ka]

[0041] [ka]

[0042] 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.

[0043] 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.

[0044] 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].

[0045] 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].

[0046] 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):

[0047] 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 Aor more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

[0048] "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.

[0049] 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.

[0050] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0051] "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.

[0052] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0053] 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.

[0054] "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.

[0055] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group.

[0056] "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.

[0057] 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.

[0058] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0059] -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), 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 -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.

[0060] -O-(R 904 ) a group represented by -O-(R 904Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) is an example. 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.

[0061] -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.

[0062] -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) is an example. 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.

[0063] "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.

[0064] "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.

[0065] "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.

[0066] "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.

[0067] "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.

[0068] "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.

[0069] "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.

[0070] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "substituted or unsubstituted 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. Multiple G3 groups 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 "unsubstituted trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0071] "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.

[0072] 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.

[0073] 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.

[0074] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0075] [ka]

[0076] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:

[0077] [ka]

[0078] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0079] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0080] [ka]

[0081] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0082] 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.

[0083] "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.

[0084] "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.

[0085] "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.

[0086] 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).

[0087] [ka]

[0088] [ka]

[0089] 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.

[0090] [ka]

[0091] 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.

[0092] [ka]

[0093] 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.

[0094] 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).

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-69) to (TEMP-82), * represents a bonding position.

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-83) to (TEMP-102), * represents a bonding position.

[0104] The above is the explanation of "substituents described in this specification."

[0105] - "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.

[0106] [ka]

[0107] For example, R 921 ~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.

[0108] 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).

[0109] [ka]

[0110] 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, R921 and R 922 and are bonded to each other to form ring Q A and R 922 and R 923 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.

[0111] [ka]

[0112] 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 Ais a fused ring.

[0113] The "unsaturated ring" is at least one ring selected from the group consisting of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring having an unsaturated bond in its ring structure, and a non-aromatic heterocyclic ring having an unsaturated bond in its ring structure. The unsaturated bond in the ring structure of the unsaturated ring is one or both of a double bond and a triple bond. Examples of aliphatic hydrocarbon rings having an unsaturated bond in their ring structure include cyclohexene and cyclohexadiene. Examples of non-aromatic heterocyclic rings having an unsaturated bond in their ring structure include dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, and isoindoline.

[0114] The "saturated ring" is at least one ring selected from an aliphatic hydrocarbon ring having no unsaturated bonds and a non-aromatic heterocyclic ring having no unsaturated bonds. The saturated ring has no double or triple bonds in the ring structure. 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 in the main skeleton, or with a plurality of atoms in the main skeleton and one or more additional atoms. For example, R 921 and R 922 and are bonded to form a ring Q 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 atoms. 921 and R 922 Todekan Q A In the case where R921 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

[0115] Here, unless otherwise specified in this specification, the "arbitrary atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In the arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), 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 atom other than a carbon atom is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary atoms" 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 rings" "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 rings 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 atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0116] 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 "saturated ring" or "unsaturated 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").

[0117] 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 R901 ~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 R 903 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.

[0118] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 50 ring carbon atoms and heterocyclic groups having 5 to 50 ring atoms.

[0119] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 18 ring carbon atoms and heterocyclic groups having 5 to 18 ring atoms.

[0120] 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."

[0121] 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. When a plurality of optional substituents are present, the plurality of optional substituents may be the same or different.

[0122] 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.

[0123] First Embodiment [Compound] The compound according to the first embodiment is a compound having a structure represented by the following general formula (1): The compound according to the first embodiment may be referred to as a first compound.

[0124] [ka]

[0125] (In the general formula (1), R 101 ~R 121 are each independently hydrogen atoms, halogen 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R 190 ) a group represented by -S-(R 191 ) 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, -C(=O)-O-(R 192 ) a group represented by -C(=O)-N(R 193 )(R 194 ) a group represented by -N(R 195 )(R 196 ) a group represented by nitro group, -Si(R 197 )(R 198 )(R 199 ) a group represented by selected from the group consisting of groups represented by the following general formula (13): R 101 ~R 121 At least one of the groups is a group represented by the following general formula (13): (In the compound having the structure represented by the general formula (1), R 190 ~R 199 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. However, R 101 ~R 121 is not a substituted or unsubstituted N-carbazolyl group, The structure represented by the general formula (1) does not have a group represented by the following general formula (12):

[0126] [ka]

[0127] (In the group represented by the general formula (12), X 1 is a nitrogen atom or CR 141 represents X 2 is a nitrogen atom or CR 142 represents X 3 is a nitrogen atom or CR 143 represents X 4 is a nitrogen atom or CR 144 represents X 5 is a nitrogen atom or CR 145 represents R 141 ~R 145 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. However, X 1 ~X 5 At least one of these is represented by a nitrogen atom. * indicates the bond position.

[0128] [ka]

[0129] (In the group represented by the general formula (13), Y is a nitrogen atom or CR 135 represents R 131 ~R 134 one or more pairs of adjacent two or more of R 135 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 131 ~R 134 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; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -L 1 -R 136 is a group represented by L 1 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, R 136 teeth, 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, * indicates the bond position.

[0130] The compound according to the first embodiment allows an organic electroluminescence device to emit light with high efficiency and a long life. The compound according to the first embodiment (first compound) has a group represented by the general formula (13) (e.g., a benzimidazole group), which deepens the ionization potential (increases the value of the ionization potential). For example, when the compound according to the first embodiment and a delayed fluorescent light-emitting material are contained in the light-emitting layer of an organic EL device, the efficiency of energy transfer from the delayed fluorescent light-emitting material to the compound according to the first embodiment improves. As a result of this improved energy transfer efficiency, the luminous efficiency of the organic EL device improves. Furthermore, the deepened ionization potential makes it more difficult for holes injected into the light-emitting layer to be injected into the compound according to the first embodiment, thereby improving the device life.

[0131] In the compound according to the first embodiment, R 101 ~R 121 It is preferable that one or two of the groups represented by the general formula (13) are groups represented by the general formula (13), and R 101 ~R 121 It is more preferable that one of the above is a group represented by the general formula (13).

[0132] In the compound according to the first embodiment, R 101 ~R 121 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0133] In the compound according to the first embodiment, R 108 , R 109 , R 110 and R 111 At least one selected from the group consisting of is preferably selected from substituents other than a hydrogen atom.

[0134] In the compound according to the first embodiment, R 108 , R 109 , R110 and R 111 is preferably selected from the group consisting of 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, even more preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0135] In the compound according to the first embodiment, R 108 , R 109 , R 110 and R 111 is selected from the group consisting of substituents other than hydrogen atoms, and R 108 , R 109 , R 110 and R 111 The remaining three of these are preferably hydrogen atoms.

[0136] In the compound according to the first embodiment, R 110 is preferably selected from 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0137] In the compound according to the first embodiment, R 110 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0138] In the compound according to the first embodiment, R 115 , R 116 , R 117 and R 118It is preferable that at least one selected from the group consisting of the following is a group represented by the general formula (13).

[0139] In the compound according to the first embodiment, R 115 , R 116 , R 117 and R 118 It is preferable that one selected from the group consisting of the following is a group represented by the general formula (13). In the compound according to the first embodiment, R 115 , R 116 , R 117 and R 118 is a group represented by the general formula (13), and R 115 , R 116 , R 117 and R 118 It is more preferable that the remaining three of the groups are hydrogen atoms.

[0140] In the compound according to the first embodiment, R 116 is preferably a group represented by the general formula (13).

[0141] In the first embodiment, it is also preferable that the structure represented by the general formula (1) is a structure represented by the following general formula (14): That is, it is also preferable that the compound according to the first embodiment is a compound having a structure represented by the following general formula (14):

[0142] [ka]

[0143] (In the general formula (14), R 101 ~R 115 and R 117 ~R 121 are R in the general formula (1), respectively. 101 ~R 115 and R 117 ~R 121 and Y and R 131 ~R 134respectively represent Y and R in the general formula (13). 131 ~R 134 is equivalent to

[0144] In the first embodiment, it is also preferable that the structure represented by the general formula (1) is a structure represented by the following general formula (15). That is, it is also preferable that the compound according to the first embodiment is a compound having a structure represented by the following general formula (15).

[0145] [ka]

[0146] (In the general formula (15), R 110 represents R in the general formula (1). 110 and Y and R 131 ~R 134 respectively represent Y and R in the general formula (13). 131 ~R 134 is equivalent to

[0147] In the compound according to the first embodiment, Y is CR 135 It is preferable that the formula be represented by the following formula:

[0148] In the compound according to the first embodiment, the group represented by the general formula (13) is preferably a group represented by the following general formula (131) or (132). That is, in the compound according to the first embodiment, R 101 ~R 121 At least one of the above is preferably a group represented by the following general formula (131) or (132): 135 When Y in the general formula (13) is a nitrogen atom, the group represented by the general formula (13) is represented by the following general formula (132).

[0149] [ka]

[0150] (In the general formulas (131) and (132), R 131 ~R 135 are R in the general formula (13), respectively. 131 ~R 135 and * indicates the bonding position.)

[0151] In the compound according to the first embodiment, R 135 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and more preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0152] In the compound according to the first embodiment, R 135 is preferably 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, more preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, even more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, and even more preferably a tert-butyl group or a substituted or unsubstituted phenyl group.

[0153] In the compound according to the first embodiment, R 131 ~R 134 It is preferred that any pair of adjacent two or more of the above groups are not bonded to each other and do not form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[0154] In the compound according to the first embodiment, R 131 ~R 134It is also preferred that one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or to form a substituted or unsubstituted fused ring. 131 ~R 134 The ring formed by one or more pairs of adjacent two or more of the groups is preferably at least one ring selected from the group consisting of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring having an unsaturated bond in the ring structure, and a non-aromatic heterocyclic ring having an unsaturated bond in the ring structure, and these rings are substituted or unsubstituted rings. 131 ~R 134 The ring formed by one or more pairs of adjacent two or more of the above is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, and more preferably a substituted or unsubstituted benzene ring. 131 ~R 134 For example, R 131 and R 132 A set consisting of R 132 and R 133 and R 133 and R 134 and it is preferred that any of these groups be bonded to each other to form the above-mentioned substituted or unsubstituted monocyclic ring, or be bonded to each other to form the above-mentioned substituted or unsubstituted fused ring.

[0155] In the compound according to the first embodiment, R 131 ~R 134 are each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0156] It is also preferable that the compound according to the first embodiment does not contain a substituted or unsubstituted N-carbazolyl group.

[0157] In the compound according to the first embodiment, R 141 ~R 145 adjacent pairs of two or more of the

[0158] In this specification, a cycloalkenyl group having 3 to 50 ring carbon atoms refers to a monovalent monocyclic group having 3 to 50 ring carbon atoms and having at least one double bond in the ring but not having aromaticity. Unless otherwise specified in this specification, the number of ring carbon atoms in the cycloalkenyl group described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6. Specific examples of the cycloalkenyl group described in this specification include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0159] In the compound according to the first embodiment, the substituent ("optional substituent") in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, an unsubstituted cycloalkenyl 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 halogen atom, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms. In the compound according to the first embodiment, R 901 ~R 907are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; R 901 If there are two or more, there are two or more R 901 are the same or different, and R 902 If there are two or more, there are two or more R 902 are the same or different, and R 903 If there are two or more, there are two or more R 903 are the same or different, and R 904 If there are two or more, there are two or more R 904 are the same or different, and R 905 If there are two or more, there are two or more R 905 are the same or different, and R 906 If there are two or more, there are two or more R 906 are the same or different, and R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0160] In the compound according to the first embodiment, the substituent in the "substituted or unsubstituted" case is also preferably a group selected from the group consisting of an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0161] In the compound according to the first embodiment, the substituent in the "substituted or unsubstituted" case is also preferably a group selected from the group consisting of an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0162] In the compound according to the first embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups. "Unsubstituted" in the case of "substituted or unsubstituted" means that a hydrogen atom is bonded to the group.

[0163] (Method for producing the first compound) The compound according to the first embodiment (first compound) can be produced according to the synthesis method described in the examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0164] (Specific Example of the First Compound) Specific examples of the compound according to the first embodiment (first compound) include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula. In this specification, a methyl group may be represented as Me, and a phenyl group may be represented as Ph.

[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168] [ka]

[0169] (Maximum peak wavelength) The maximum peak wavelength of the first compound according to this embodiment (a compound having a structure represented by the general formula (1)) is preferably 500 nm or more and 560 nm or less, preferably 510 nm or more and 550 nm or less, and more preferably 515 nm or more and 540 nm or less. The first compound according to this embodiment preferably exhibits green emission. In this specification, green emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 500 nm or more and 560 nm or less.

[0170] In this specification, the method for measuring the maximum peak wavelength of a compound is as follows. -6 mol / L or more, 10 -5 A toluene solution containing the compound dissolved at a concentration of 100 mol / L or less is prepared and placed in a quartz cell. The emission spectrum of this sample (toluene solution) is measured at room temperature (300 K) using a spectrofluorometer. The vertical axis of the emission spectrum represents emission intensity, and the horizontal axis represents wavelength. The emission spectrum can be measured, for example, using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measurement device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the maximum peak wavelength. Note that in this specification, the maximum peak wavelength of the fluorescent emission may also be referred to as the maximum fluorescent emission peak wavelength. The emission half width FWHM is the full width at half maximum at the maximum peak of the emission spectrum.

[0171] Second Embodiment [Light-emitting element materials] The light-emitting device material according to this embodiment contains the compound according to the first embodiment. The light-emitting device material refers to a material used in any layer of the light-emitting device. One aspect of the light-emitting device material includes only the compound according to the first embodiment, and another aspect of the light-emitting device material includes the compound according to the first embodiment and another compound different from the compound according to the first embodiment. In the light-emitting device material of this embodiment, the compound according to the first embodiment (a compound having a structure represented by the general formula (1)) is preferably a dopant material. In this case, the light-emitting device material may contain the compound according to the first embodiment as a dopant material and other compounds such as a host material.

[0172] Third Embodiment [Organic electroluminescence element] In this embodiment, an organic EL element will be described as a light emitting element. The organic EL device according to this embodiment includes a cathode, an anode, and an organic layer between the cathode and the anode. The organic layer includes one or more layers. At least one of the layers includes the compound according to the first embodiment as a first compound. For example, the organic layer is formed by laminating multiple layers made of organic compounds. The organic layer includes a light-emitting layer. The organic layer may further include an inorganic substance (at least one of an inorganic compound and a simple substance). A layer containing an inorganic substance may be included between the cathode and the anode.

[0173] The organic layer may be composed of, for example, a single light-emitting layer, or may include a layer that can be used in an organic EL device. The layer that can be used in an organic EL device is not particularly limited, and examples thereof 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, and a blocking layer.

[0174] FIG. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL device 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is configured by laminating a hole injection layer 6, a hole transport layer 7, an emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side.

[0175] (light-emitting layer) In the organic EL device according to this embodiment, at least one of the layers included in the organic layer is an emitting layer, and the emitting layer preferably contains the compound according to the first embodiment (first compound).

[0176] In the organic EL device according to this embodiment, it is also preferable that the light-emitting layer further contains a second compound having delayed fluorescence.

[0177] In the organic EL device according to this embodiment, the light-emitting layer preferably contains a first compound and a second compound. The first compound in the light-emitting layer is preferably the compound according to the first embodiment. In this embodiment, the second compound is preferably a host material (sometimes referred to as a matrix material), and the first compound is preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material).

[0178] In this specification, the term "host material" refers to a material that is contained in, for example, "50% by mass or more of the layer." Thus, for example, the light-emitting layer contains the second compound in an amount of 50% by mass or more of the total mass of the light-emitting layer. Furthermore, for example, the "host material" may be contained in an amount of 60% by mass or more of the layer, 70% by mass or more of the layer, 80% by mass or more of the layer, 90% by mass or more of the layer, or 95% by mass or more of the layer.

[0179] When the organic EL device of this embodiment is caused to emit light, it is preferable that the compound according to the first embodiment as the first compound mainly emits light in the light-emitting layer.

[0180] In one embodiment, the light-emitting layer may include a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, the light-emitting layer preferably does not contain a phosphorescent material (dopant material). In one embodiment, the light-emitting layer preferably does not contain heavy metal complexes or phosphorescent rare earth metal complexes, such as iridium complexes, osmium complexes, and platinum complexes.

[0181] In this embodiment, when the light-emitting layer contains the compound according to the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0182] (First Compound) In the organic EL device according to this embodiment, the first compound is preferably the compound according to embodiment 1. In one embodiment, the first compound is a fluorescent compound that does not exhibit delayed fluorescence.

[0183] (Second Compound) In the organic EL device according to this embodiment, the second compound is not particularly limited, but it is preferable that the second compound is a delayed fluorescent light-emitting material.

[0184] In the organic EL device of this embodiment, the delayed fluorescent light-emitting material as the second compound is preferably a host material. In the organic EL device of this embodiment, it is preferable that the delayed fluorescent light-emitting material as the second compound is a host material, and the compound according to the first embodiment as the first compound is a dopant material.

[0185] (delayed fluorescence) Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is 13 It is explained that if the transition probability can be reduced, the reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state occurs with high efficiency, resulting in the manifestation of thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document explains the mechanism by which delayed fluorescence occurs. The delayed fluorescent light-emitting material in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence that occurs through such a mechanism.

[0186] Generally, delayed fluorescence can be confirmed by transient PL (photoluminescence) measurement.

[0187] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a technique in which a sample is excited by irradiating it with a pulsed laser, and then the decay behavior (transient characteristics) of the PL emission is measured after the irradiation is stopped. PL emission from TADF materials is classified into emission components from singlet excitons generated during the initial PL excitation, and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the initial PL excitation is extremely short, on the order of nanoseconds. Therefore, the emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between the emission from the singlet excitons generated by the initial PL excitation and the emission from the singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be measured.

[0188] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Figure 2. An example of a method for measuring transient PL and an analysis of the behavior of delayed fluorescence will be described below using Figure 2.

[0189] 2 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG. 2.

[0190] The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, in which the matrix material is doped with a doping material at a concentration of 12 mass %.

[0191] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample placed in the sample chamber 102 to excite the doping material. Emission light is extracted in a direction 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by the spectrometer 103, forming a two-dimensional image in the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. By cutting out this two-dimensional image along a predetermined time axis, an emission spectrum can be obtained in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, by cutting out the two-dimensional image along the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[0192] For example, a thin film sample A was prepared as described above using the following compound HX1 as the matrix material and the following compound DX1 as the doping material, and transient PL measurement was carried out.

[0193] [ka]

[0194] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following compound HX2 as a matrix material and the above-mentioned compound DX1 as a doping material.

[0195] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0196] [ka]

[0197] As described above, transient PL measurements can be used to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by back energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly, is somewhat larger.

[0198] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) with a wavelength that the delayed fluorescent material absorbs. Delayed luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0199] The amounts of prompt luminescence and delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amounts of prompt luminescence and delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2.

[0200] In this specification, the delayed fluorescence of a delayed fluorescent material is measured using a sample prepared by the following method. For example, the delayed fluorescent material is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. To prevent quenching by oxygen, the sample solution is frozen and degassed, and then sealed in a lidded cell under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra according to equation (1) in Morris et al., J. Phys. Chem. 80 (1976) 969.

[0201] In this embodiment, the amount of prompt luminescence (prompt luminescence) of the compound to be measured (delayed fluorescent material) is calculated as X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. The amounts and ratio of prompt luminescence and delayed luminescence of compounds other than delayed fluorescent luminescent materials in this specification are measured in the same manner as the amounts and ratio of prompt luminescence and delayed luminescence of delayed fluorescent luminescent materials.

[0202] (ΔST) In this embodiment, the lowest excited singlet energy S1 and the energy gap T at 77 [K] 77K The difference between (S1-T 77K ) is defined as ΔST.

[0203] The lowest excited singlet energy S1(M2) of the delayed fluorescent emitting material and the energy gap T at 77[K] of the delayed fluorescent emitting material 77K The difference ΔST(M2) from (M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the relationship of the following mathematical formula (10), (11), (12), or (13). ΔST(M2)=S1(M2)-T 77K (M2)<0.3eV…(Number 10) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV …(Math. 11) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV …(Math. 12) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV …(Math. 13)

[0204] (Relationship between triplet energy and energy gap at 77[K]) Here, the relationship between the triplet energy and the energy gap at 77 K will be described. In this embodiment, the energy gap at 77 K differs from the triplet energy that is usually defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77 K). A tangent line is drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated using a predetermined conversion formula based on the wavelength value at the intersection of the tangent line and the horizontal axis. Here, the thermally activated delayed fluorescent compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), resulting in a mixture of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as above contains light emission from both the excited singlet and excited triplet states, and although it is difficult to clearly distinguish which state the light emission originates from, the triplet energy value is considered to be fundamentally dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that it is different in the strict sense, the value measured as follows is referred to as the energy gap T 77KThe compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is placed in a quartz cell to serve as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. edge Based on the [nm], the amount of energy calculated using the following conversion formula (F1) is the energy gap T at 77 [K]. 77K Let's say. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0205] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity that is 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is defined as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light-receiving device.

[0206] (Lowest excited singlet energy S1) The following method can be used to measure the lowest excited singlet energy S1 using a solution (sometimes referred to as a solution method). A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0207] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum values ​​on the longest wavelength side.

[0208] (Relationship between the first compound and the second compound in the light-emitting layer) In the organic EL device according to this embodiment, when the emitting layer contains the compound according to the first embodiment (first compound) and a delayed fluorescent light-emitting material, it is preferable that the lowest excited singlet energy S1(M2) of the second compound (delayed fluorescent light-emitting material) and the lowest excited singlet energy S1(M1) of the first compound satisfy the following mathematical formula (Mathematical Formula 1): S1(M2)>S1(M1)…(Math 1)

[0209] In the organic EL device according to this embodiment, the energy gap T 77K(M1) is the energy gap T at 77[K] of the second compound 77K It is preferable that the value is smaller than (M2). In other words, it is preferable that the relationship of the following mathematical formula (Mathematical Formula 3) is satisfied. T 77K (M2)>T 77K (M1) ... (Number 3)

[0210] (Compound represented by general formula (20)) In this embodiment, the delayed fluorescent light-emitting material as the second compound is not particularly limited as long as it is a compound having delayed fluorescence. In one embodiment, the delayed fluorescent light-emitting material as the second compound is a compound represented by the following general formula (20):

[0211] [ka]

[0212] (In the general formula (20), D X is a group represented by the following general formula (21), (22) or (23), provided that at least one D X is a group represented by the following general formula (22) or (23): m is 1, 2, 3 or 4, and when m is 2, 3 or 4, a plurality of D X are identical to or different from each other, R is independently hydrogen atoms, halogen atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, -Si(R 291 )(R 292 )(R 293 ) a group represented by -O-(R 294 ) a group represented by -S-(R 295 ) a group represented by -N(R 296 )(R 297 ) a group represented by n is 0, 1, 2, or 3, and when n is 2 or 3, the multiple Rs are the same or different, and the sum of n and m is 4.

[0213] [ka]

[0214] [ka]

[0215] (R in the general formula (21) 21 ~R 28 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 in the general formula (22) 221 ~R 228 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 in the general formula (23) 231 ~R 238 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 monocyclic ring and does not form the substituted or unsubstituted fused ring 21 ~R28 , R 221 ~R 228 and R 231 ~R 238 are each independently hydrogen atoms, halogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, -Si(R 291 )(R 292 )(R 293 ) a group represented by -O-(R 294 ) a group represented by -S-(R 295 ) a group represented by -N(R 296 )(R 297 ) is a group represented by In the general formulas (22) and (23), A2, B2, and C2 are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (24), (25), and (26), and the ring structure A2, the ring structure B2, and the ring structure C2 are fused with an adjacent ring structure at any position, p, px, and py are each independently 1, 2, 3, or 4; When p is 2, 3 or 4, the multiple ring structures A2 are the same or different from each other, When px is 2, 3 or 4, the multiple ring structures B2 are the same or different from each other, When py is 2, 3 or 4, the ring structures C2 are the same or different from each other, However, at least one D Xis a group represented by general formula (22) in which p is 2, 3, or 4, and which contains, as ring structure A2, any ring structure selected from the group consisting of ring structures represented by general formulas (25) and (26) below, or is a group represented by general formula (23) in which at least one of px and py is 2, 3, or 4, and which contains, as ring structure B2 or ring structure C2, any ring structure selected from the group consisting of ring structures represented by general formulas (25) and (26) below, * in the general formulae (21), (22), and (23) indicates the bonding position to the benzene ring in the general formula (20).

[0216] [ka]

[0217] (In the general formula (24), R 229 and R 230 One or more of the pairs 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, In the general formulas (25) and (26), X 21 and X 22 are each independently, NR 220 , a sulfur atom, or an oxygen atom; R 220 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 229 and R 230 are each independently hydrogen atoms, halogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, -Si(R291 )(R 292 )(R 293 ) a group represented by -O-(R 294 ) a group represented by -S-(R 295 ) a group represented by -N(R 296 )(R 297 ) is a group represented by

[0218] (In the second compound, R 291 ~R 297 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0219] In the second compound, R 291 If there are multiple R 291 are the same or different, and R 292 If there are multiple R 292 are the same or different from each other, and R 293 If there are multiple R 293 are the same or different, and R 294 If there are multiple R 294 are the same or different from each other, and R 295 If there are multiple R 295 are the same or different from each other, and R 296 If there are multiple R 296 are the same or different, and R 297 If there are multiple R 297 are the same or different from each other.

[0220] In the compound represented by the general formula (20), the benzene ring of the general formula (20) to which the groups represented by the general formulas (21), (22), and (23) are bonded is the benzene ring itself explicitly shown in the general formula (20), and R and D X It is not a benzene ring contained in

[0221] In the compound represented by the general formula (20), it is also preferable that at least one R is a substituent rather than a hydrogen atom or a halogen atom, and that at least one R as the substituent is bonded to the benzene ring in the general formula (20) via a carbon-carbon bond.

[0222] In the compound represented by the general formula (20), the sum of the number of R substituents and the number of groups represented by the general formula (22) or (23) is preferably 3 or 4.

[0223] In the general formula (20), each R is preferably independently a hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms. In the general formulas (21), (22) and (23), R 21 ~R 28 , R 221 ~R 228 , and R 231 ~R 238 are preferably each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms. In the general formula (22), p is preferably 2, 3 or 4. In the general formula (23), px and py are preferably each independently 2, 3, or 4.

[0224] (Method for producing delayed fluorescent light-emitting material) The delayed fluorescent light-emitting material can be produced by a known method. Alternatively, the delayed fluorescent light-emitting material can be produced by following a known method and using known alternative reactions and raw materials suited to the target product.

[0225] (Specific examples of delayed fluorescent light-emitting materials) Specific examples of delayed fluorescent light-emitting materials include the following compounds: However, the present invention is not limited to these specific examples of delayed fluorescent light-emitting materials.

[0226] [ka]

[0227] [ka]

[0228] (TADF mechanism) 4 is a diagram showing an example of the relationship between the energy levels of the second compound M2 when it is a delayed fluorescent light-emitting material and the first compound M1 when it is a compound of the first embodiment in an emitting layer. In FIG. 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound M1. T1(M1) represents the lowest excited triplet state of the first compound M1. S1(M2) represents the lowest excited singlet state of the second compound M2. T1(M2) represents the lowest excited triplet state of the second compound M2. The dashed arrow from S1(M2) to S1(M1) in FIG. 4 represents a Förster type energy transfer from the lowest excited singlet state of the second compound M2 to the first compound M1. As shown in Figure 4, when a compound with a small ΔST(M2) (delayed fluorescent light-emitting material) is used as the second compound M2, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound M2 to the first compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound M1 can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence via this TADF mechanism.

[0229] The second compound as the host material may be a compound having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the first compound as the dopant material. Examples of the host material include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives, (3) fused aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives, (4) fused heterocyclic compounds such as carbazole derivatives, and (5) aromatic amine compounds such as triarylamine derivatives and fused polycyclic aromatic amine derivatives.

[0230] (Light emission from organic EL elements) When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound in the light-emitting layer mainly emits light.

[0231] The organic EL element of this embodiment preferably emits green light. When the organic EL element of this embodiment emits green light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.

[0232] The maximum peak wavelength of light emitted from the organic EL element is measured as follows. Current density is 10mA / cm2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer. In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm). As the spectroradiance meter, for example, a spectroradiance meter CS-2000 manufactured by Konica Minolta, Inc. can be used. Note that the spectral radiance spectrum measuring device is not limited to this device.

[0233] (Thickness of the light-emitting layer) The thickness of the light-emitting layer in the organic EL device of this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less. When the thickness of the light-emitting layer is 5 nm or more, the formation of the light-emitting layer and the adjustment of chromaticity tend to be easy. When the thickness of the light-emitting layer is 50 nm or less, an increase in driving voltage is easily suppressed.

[0234] (Compound content in the light-emitting layer) In the organic EL device of this embodiment, the contents of the first compound and the second compound contained in the light-emitting layer are preferably within the following ranges, for example. The content of the first compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The upper limit of the total content of the first compound and the second compound in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the case where the light-emitting layer contains materials other than the first compound and the second compound. The light-emitting layer may contain only one type of first compound or two or more types thereof. The light-emitting layer may contain only one type of second compound or two or more types thereof.

[0235] The structure of the organic EL element will be further explained.

[0236] (substrate) The substrate is used as a support for the organic EL element. Examples of materials that can be used for the substrate include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films may also be used.

[0237] (anode) The anode formed on the substrate is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or higher). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride). These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% by mass or more and 10% by mass or less of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like. Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that easily injects holes regardless of the work function of the anode, so materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used. These include alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these metals (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these metals. Vacuum deposition and sputtering can be used to form the anode using alkali metals, alkaline earth metals, and alloys containing these metals. Furthermore, when using silver paste, coating and inkjet printing can be used.

[0238] When the organic EL device is a bottom-emission type, the anode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light from the light-emitting layer. In this specification, light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the anode section.

[0239] When the organic EL device is a top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode. The anode may be composed of only a reflective layer, or may have a multilayer structure including a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is disposed between the reflective layer and the hole transport region. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0240] (cathode) The cathode is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be deposited by sputtering, inkjet printing, spin coating, etc.

[0241] When the organic EL device is a bottom-emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed of a metal material having light reflectivity. The metal material having light reflectivity can be appropriately selected from the materials listed in the cathode section.

[0242] When the organic EL device is a top-emission type, the cathode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the cathode section.

[0243] 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. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflection. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflective electrode having light reflectivity, and the cathode is a light-transmitting electrode having light transmittance.

[0244] (capping layer) When the organic EL device is a top-emission type, the organic EL device usually has a capping layer on the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives. A laminate obtained by stacking layers containing these substances can also be used as the capping layer.

[0245] (hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, or manganese oxide. In addition, materials with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1, Other examples include aromatic amine compounds such as 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1). Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Acid-added polymeric compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0246] (Hole transport layer) In the organic EL device according to this embodiment, it is preferable that a hole transport layer is included between the anode and the light-emitting layer. The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2- ... Aromatic amine compounds such as phenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 It is a material with a hole mobility of 1 / Vs or more. The hole-transporting layer may be formed using carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used. However, other substances may also be used as long as they have a higher hole-transporting capacity than electron-transporting capacity. The layer containing the substance with a high hole-transporting capacity may be a single layer or a layer in which two or more layers made of the above-mentioned substances are stacked.

[0247] (electron barrier layer) In the organic EL device according to this embodiment, an electron blocking layer is preferably included between the anode and the light-emitting layer, and more preferably between the hole transport layer and the light-emitting layer. The electron blocking layer is preferably a layer that transports holes and blocks electrons from reaching a layer (e.g., the hole transport layer) closer to the anode than the electron blocking layer. The compound contained in the electron blocking layer is, for example, a compound used in known electron blocking layers, and is preferably at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. The compound contained in the electron blocking layer may also be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. The compound contained in the electron blocking layer may also be a compound having a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. In the organic EL device according to this embodiment, the compound contained in the electron blocking layer is also preferably a monoamine compound containing one or more rings selected from the group consisting of a substituted or unsubstituted carbazole ring, a substituted or unsubstituted dibenzofuran ring, and a substituted or unsubstituted fluorene ring. The electron blocking layer may be a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the anode than the electron blocking layer (e.g., a hole transport layer and a hole injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.

[0248] (hole blocking layer) In the organic EL device according to this embodiment, a hole blocking layer is preferably included between the cathode and the light-emitting layer, and more preferably between the electron transport layer and the light-emitting layer. The hole blocking layer is preferably a layer that transports electrons and prevents holes from reaching a layer (e.g., the electron transport layer) closer to the cathode than the hole blocking layer. The compound contained in the hole blocking layer is, for example, a compound used in known hole blocking layers. The compound contained in the hole blocking layer is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described below. The compound contained in the hole blocking layer may also be, for example, at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. In the organic EL device according to this embodiment, the compound contained in the hole-blocking layer is preferably a compound having a substituted or unsubstituted azine ring and a substituted or unsubstituted carbazole ring, a compound having a substituted or unsubstituted azine ring and a substituted or unsubstituted fluorene ring, or a compound having a substituted or unsubstituted azine ring and a substituted or unsubstituted dibenzofuran ring. In the organic EL device according to this embodiment, the azine ring contained in the compound contained in the hole-blocking layer is preferably at least one of a substituted or unsubstituted pyrimidine ring and a substituted or unsubstituted triazine ring. It is also preferable that the hole blocking layer is a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the cathode than the hole blocking layer (for example, an electron transport layer or an electron injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.

[0249] (electron transport layer) In the organic EL device according to this embodiment, an electron transport layer is preferably included between the cathode and the light-emitting layer. The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can be made of 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; or 3) polymeric compounds. Specifically, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used as low-molecular-weight organic compounds. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances mentioned here are mainly from the 10 -6 cm 2 The electron-transporting layer is a substance having an electron mobility of 1 / Vs or higher. Note that any substance other than those mentioned above may be used as the electron-transporting layer as long as it has a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be a single layer or a stack of two or more layers made of the above-mentioned substances. The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0250] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), and lithium oxide (LiOx), or compounds thereof can be used. Alternatively, a substance with electron transport properties containing an alkali metal, alkaline earth metal, or compound thereof, such as magnesium (Mg) in Alq, can be used. In this case, electron injection from the cathode can be more efficiently performed. Alternatively, a composite material containing an organic compound and an electron donor (donor) can be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties. Specifically, the aforementioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, including lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, including lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (TTF) can also be used.

[0251] (Layer formation method) The method for forming each layer of the organic EL element of this embodiment is not limited to those specifically mentioned above, but known methods can be used, such as dry film formation methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet film formation methods such as spin coating, dipping, flow coating, and inkjet deposition.

[0252] (film thickness) The thickness of each organic layer in the organic EL element of the present embodiment is not limited except as specifically mentioned above. However, if the thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a thickness in the range of several nm to 1 μm is usually preferred.

[0253] According to this embodiment, at least one organic layer contains the compound of the first embodiment, so that a high-performance organic EL device is realized. According to one embodiment, an organic EL device that emits light with high efficiency and a long life is realized. The organic EL device according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0254] Fourth Embodiment [Organic electroluminescence element] The configuration of an organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0255] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer further contains a third compound, but is otherwise similar to the organic EL device according to the third embodiment.

[0256] In the fourth embodiment, the emitting layer preferably includes a first compound, a second compound, and a third compound. In this embodiment, the first compound is more preferably the compound of the first embodiment, and the second compound is even more preferably a delayed fluorescent light-emitting material. In this embodiment, the first compound is preferably a dopant material, and the second compound is preferably a host material. The third compound is preferably a host material. The third compound is preferably not a dopant material. For example, the emitting layer of the fourth embodiment may contain the second compound and the third compound in a total amount of 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the total mass of the emitting layer.

[0257] (Third Compound) In the organic EL device according to this embodiment, the third compound may be a delayed fluorescent compound or a compound that does not exhibit delayed fluorescence, but is preferably a compound that does not exhibit delayed fluorescence. The third compound is not particularly limited, but is preferably a compound other than an amine compound. That is, it is preferable that the third compound does not contain a substituted or unsubstituted amino group. Furthermore, for example, the third compound may be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.

[0258] (Compound represented by general formula (3X)) In the organic EL device according to this embodiment, the third compound is also preferably a compound represented by the following general formula (3X).

[0259] [ka]

[0260] (In the general formula (3X), A3 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, L3 is single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, R 31 ~R 38 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 monocyclic ring and does not form the substituted or unsubstituted fused ring 31 ~R 38 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(R906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) 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 a group represented by the following general formula (3A):

[0261] [ka]

[0262] (In the general formula (3A), R B teeth, 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 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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 B When there are multiple R B are the same or different from each other, L 31 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the heterocyclic group, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the divalent group; L 32 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, n3 is 1, 2, 3, 4 or 5; L 31 is a single bond, n3 is 1, and L 32 is bonded to a carbon atom of the six-membered ring in the general formula (3X), L 32 When there are multiple L 32 are the same or different from each other, * represents the bonding site to the carbon atom of the six-membered ring in the general formula (3X).

[0263] (In the third compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 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 903are 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 908 If there are multiple R 908 are the same or different from each other, R 909 If there are multiple R 909 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.)

[0264] In the organic EL device according to this embodiment, the third compound is also preferably a compound represented by any one of the following general formulas (31) to (36).

[0265] [ka]

[0266] [ka]

[0267] [ka]

[0268] (In the general formulas (31) to (36), A3 and L3 are defined as A3 and L3 in the general formula (3X), respectively. R 341 ~R 350 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, X 31 is a sulfur atom, an oxygen atom, and NR 352 or C(R 353 )(R 354 ) and R 353 and R 354 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, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 341 ~R 350 and R 352and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 353 and R 354 and R each independently represent a group that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0269] In the third compound, R 352 is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0270] In the third compound, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 353 and R 354 are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0271] In the third compound, X 31 is preferably a sulfur atom or an oxygen atom.

[0272] In the third compound, A3 is preferably a group represented by any one of the following general formulae (A31) to (A37).

[0273] [ka]

[0274] [ka]

[0275] [ka]

[0276] [ka]

[0277] (In the general formulae (A31) to (A37), Multiple R 300 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 333 and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 300 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is synonymous with * in the general formulae (A31) to (A37) indicates the bonding position of L3 in the third compound.

[0278] In the third compound, A3 is also preferably a group represented by the general formula (A34), (A35) or (A37).

[0279] The third compound is also preferably a compound represented by any one of the following general formulas (311) to (316).

[0280] [ka]

[0281] [ka]

[0282] [ka]

[0283] [ka]

[0284] [ka]

[0285] [ka]

[0286] (In the general formulae (311) to (316), L3 has the same meaning as L3 in general formula (3X). Multiple R 300 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 341 ~R 350 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 monocyclic ring and does not form the substituted or unsubstituted fused ring 300 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 341 ~R 350 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0287] The third compound is also preferably a compound represented by the following general formula (321).

[0288] [ka]

[0289] (In the general formula (321), L3 has the same meaning as L3 in general formula (3X). R 31 ~R 38 , and R 301 ~R 308 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0290] In the third compound, L3 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0291] In the third compound, L3 is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0292] In the third compound, L3 is preferably a group represented by the following general formula (317).

[0293] [ka]

[0294] (In the general formula (317), R 310 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 and * each independently indicates a bonding position.)

[0295] In the third compound, L3 also preferably contains a divalent group represented by the following general formula (318) or general formula (319). In the third compound, L3 is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0296] The third compound is also preferably a compound represented by the following general formula (322) or general formula (323).

[0297] [ka]

[0298] [ka]

[0299] (In the general formulas (322) and (323), L 33 teeth, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, L 33 includes a divalent group represented by the following general formula (318) or (319): R 31 ~R 38 , R 300 , and R 321 ~R 328 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0300] [ka]

[0301] (In the general formula (319), Multiple R 304 a pair of adjacent two of these is bonded to each other to form a ring represented by the general formula (320), In the general formula (320), 1* and 2* each independently represent R 304 indicates the bonding position with the ring to which it is attached, R in the general formula (318) 302 , R in the general formula (319) 303 R which does not form a ring represented by the general formula (320) 304 and R in the general formula (320) 305 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is synonymous with In the general formulae (318) to (320), * indicates the bonding position.

[0302] In the third compound, L or L 33 The group represented by the general formula (319) as above is, for example, a group represented by the following general formula (319A).

[0303] [ka]

[0304] (In the general formula (319A), R 303 , R 304 and R 305 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 and * in the general formula (319A) indicates the bonding position.)

[0305] The third compound is a compound represented by the general formula (322), and L 33 is also preferably a group represented by the general formula (318).

[0306] The third compound is also preferably a compound represented by the following general formula (324).

[0307] [ka]

[0308] (In the general formula (324), R 31 ~R 38 , R 300 , and R 302 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0309] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (3A), and R in the general formula (3A) B is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0310] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (3A), and R in the general formula (3A) Bis preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0311] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a group represented by the general formula (3A), and R B is preferably a substituted or unsubstituted phenyl group.

[0312] It is also preferable that the third compound is a compound that does not have a pyridine ring, a pyrimidine ring, or a triazine ring.

[0313] (Method for producing the third compound) The third compound can be produced by a known method. Alternatively, the third compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0314] (Specific Example of the Third Compound) Specific examples of the third compound according to this embodiment are shown below: Note that the third compound in the present invention is not limited to these specific examples.

[0315] [ka]

[0316] [ka]

[0317] [ka]

[0318] [ka]

[0319]

change

[0320]

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[0321]

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[0322]

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[0323]

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[0324]

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[0325]

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[0326]

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[0327]

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[0328]

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[0329]

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[0330]

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[0331]

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[0332]

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[0333]

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[0334]

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[0335]

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[0336]

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[0337]

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[0338]

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[0339]

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[0340] [ka]

[0341] (Relationship between the first compound, the second compound, and the third compound in the light-emitting layer) In the organic EL device of the present embodiment, when the light-emitting layer contains a second compound and a third compound, it is preferable that the lowest excited singlet energy S1(M2) of the second compound and the lowest excited singlet energy S1(M3) of the third compound satisfy the following mathematical formula (Mathematical Formula 2): S1(M3)>S1(M2)…(Math 2)

[0342] Energy gap T at 77[K] of the third compound 77K (M3) is the energy gap T of the first compound at 77[K]. 77K It is preferable that it is larger than (M1). Energy gap T at 77[K] of the third compound 77K (M3) is the energy gap T at 77[K] of the second compound 77K It is preferable that it is larger than (M2).

[0343] It is preferable that the lowest excited singlet energy S1(M1) of the first compound, the lowest excited singlet energy S1(M2) of the second compound, and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2A). S1(M3)>S1(M2)>S1(M1)…(Number 2A)

[0344] Energy gap T of the first compound at 77[K] 77K (M1) and the energy gap T at 77[K] of the second compound 77K (M2) and the energy gap T at 77[K] of the third compound 77K It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical Formula 2B). T 77K (M3)>T 77K (M2)>T77K (M1) ... (Math 2B)

[0345] (Compound content in the light-emitting layer) In the organic EL element of the present embodiment, when the light-emitting layer contains the first compound, the second compound, and the third compound, the contents of the first compound, the second compound, and the third compound in the light-emitting layer are preferably, for example, in the following ranges. In the organic EL element of this embodiment, the content of the first compound in the light-emitting layer is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the third compound is preferably 10% by mass or more and 80% by mass or less. The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the light-emitting layer containing materials other than the first compound, the second compound, and the third compound. The light-emitting layer may contain only one type of first compound or two or more types. The light-emitting layer may contain only one type of second compound or two or more types. The light-emitting layer may contain only one type of third compound or two or more types.

[0346] (Light emission from organic EL elements) When the organic EL device of this embodiment is caused to emit light, it is preferable that the compound of the first embodiment mainly emits light in the light-emitting layer. When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound in the light-emitting layer mainly emits light.

[0347] The organic EL element of this embodiment preferably emits green light, similarly to the organic EL element of Embodiment 3. The maximum peak wavelength of light emitted from the organic EL element can be measured in the same manner as for the organic EL element of Embodiment 3.

[0348] (TADF mechanism) FIG. 5 shows an example of the relationship between the energy levels of the first compound M1, the second compound M2, and the third compound M3 in the light-emitting layer. In FIG. 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound M1, and T1(M1) represents the lowest excited triplet state of the first compound M1. S1(M2) represents the lowest excited singlet state of the second compound M2, and T1(M2) represents the lowest excited triplet state of the second compound M2. S1(M3) represents the lowest excited singlet state of the third compound M3, and T1(M3) represents the lowest excited triplet state of the third compound M3. The dashed arrow from S1(M2) to S1(M1) in FIG. 5 represents Förster energy transfer from the lowest excited singlet state of the second compound M2 to the first compound M1. As shown in Figure 5, when a compound with a small ΔST(M2) (delayed fluorescent material) is used as the second compound M2, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound M2 to the first compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound M1 can be observed. It is believed that the use of delayed fluorescence via this TADF mechanism can theoretically increase the internal quantum efficiency to 100%.

[0349] According to this embodiment, at least one organic layer contains the compound of the first embodiment, so that a high-performance organic EL device is realized. According to one embodiment, an organic EL device that emits light with high efficiency and a long life is realized. The organic EL device according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0350] Fifth Embodiment (electronic equipment) The electronic device according to this embodiment is equipped with the organic EL element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting fixtures. The light-emitting device can be used in a display device, for example, as a backlight for a display device.

[0351] [Modification of the embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.

[0352] For example, the number of light-emitting layers is not limited to one, and multiple light-emitting layers may be stacked. When the organic EL device has multiple light-emitting layers, it is sufficient that at least one of the organic layers satisfies the conditions described in the above embodiment, and it is preferable that at least one of the light-emitting layers contains the compound of the first embodiment. When one of the multiple light-emitting layers contains the compound of the first embodiment, for example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0353] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope of achieving the object of the present invention. [Example]

[0354] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0355] <Compound> The compounds having a structure represented by general formula (1) used in the production of the organic EL devices according to Examples 1 and 2 are shown below.

[0356] [ka]

[0357] The comparative compounds used in the production of the organic EL device according to Comparative Example 1 are shown below.

[0358] [ka]

[0359] Other compounds used in the production of the organic EL devices according to Examples 1 and 2 and Comparative Example 1 are shown below.

[0360] [ka]

[0361] [ka]

[0362] [ka]

[0363] <Fabrication of organic EL elements> An organic EL device was fabricated and evaluated as follows.

[0364] Example 1 A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate with the cleaned transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus, and first, compound HT-1 and compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The proportion of compound HT-1 in the hole injection layer was 97 mass %, and the proportion of compound HA was 3 mass %. Next, the compound HT-1 was vapor-deposited on the hole injection layer to form a hole transport layer having a thickness of 90 nm. Next, compound HT-2 was vapor-deposited on the hole transport layer to form an electron blocking layer with a thickness of 30 nm. Next, on the second hole transport layer, a compound HOST as a host material (third compound), a compound TADF as a delayed fluorescent light-emitting material (second compound), and a compound GD-A as a fluorescent light-emitting material (first compound) were co-deposited to form an emitting layer with a thickness of 25 nm. The proportion of the compound HOST in the emitting layer was 74.4 mass%, the proportion of the compound TADF was 25 mass%, and the proportion of the compound GD-A was 0.6 mass%. Next, the compound ET-1 was vapor-deposited on the light-emitting layer to form a hole-blocking layer having a thickness of 5 nm. Next, the compounds ET-2 and Liq were co-deposited on the hole blocking layer to form an electron transport layer with a thickness of 50 nm. The proportion of the compound ET-2 in the electron transport layer was 50 mass %, and the proportion of Liq was 50 mass %. Liq is an abbreviation for (8-quinolinolato)lithium. Next, ytterbium (Yb) was vapor deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on the electron injection layer to form a metallic Al cathode with a film thickness of 80 nm. In this manner, a bottom-emission organic EL element according to Example 1 was fabricated. The device configuration of the organic EL device according to Example 1 is shown in outline below. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(90) / HT-2(30) / HOST:TADF:GD-A(25,74.4%:25%:0.6%) / ET-1(5) / ET-2:Liq(50,50%:50%) / Yb(1) / Al(80) In the above device configurations, the numbers in parentheses indicate film thicknesses (unit: nm). Similarly, in the above device configurations, the numbers in parentheses expressed as percentages (97%:3%) indicate the proportions (mass%) of compound HT-1 and compound HA in the hole injection layer, the numbers in percentages (74.4%:25%:0.6%) indicate the proportions (mass%) of compound HOST, compound TADF, and compound GD-A in the light-emitting layer, and the numbers in percentages (50%:50%) indicate the proportions (mass%) of compound ET-2 and Liq in the electron transport layer.

[0365] Example 2 The organic EL element of Example 2 was produced in the same manner as the organic EL element of Example 1, except that the compound GD-A in the light-emitting layer of the organic EL element of Example 1 was changed to the first compound shown in Table 1.

[0366] (Comparative Example 1) The organic EL element of Comparative Example 1 was produced in the same manner as the organic EL element of Example 1, except that the compound GD-A in the light-emitting layer of the organic EL element of Example 1 was changed to a compound shown in Table 1.

[0367] <Evaluation of organic EL elements> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 1. Table 1 also shows the lowest excited singlet energy S1 of the first compound, second compound, and third compound used in the emitting layer of each example.

[0368] (driving voltage) The current density between the anode and cathode of the fabricated organic EL device was 10 mA / cm 2 The voltage (unit: V) was measured when electricity was applied so that Based on the measured value of the driving voltage of each example (Example 1, Example 2, and Comparative Example 1) and the following mathematical formula (Mathematical Formula 1X), the "driving voltage (relative value)" (unit: %) was calculated. Driving voltage (relative value) = (driving voltage of each example / driving voltage of Comparative Example 1) × 100...(Number 1X)

[0369] (CIE1931 chromaticity) The current density of the fabricated organic EL device was 10 mA / cm 2 The CIE1931 chromaticity coordinates (x, y) when a voltage was applied so as to satisfy the following equation were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0370] (Maximum peak wavelength λ when the element is driven EL and emission half-width FWHM) The current density of the fabricated organic EL device was 10 mA / cm 2 The spectral radiance spectrum when a voltage was applied so that the maximum peak wavelength λ was obtained was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). EL The full width at half maximum (FWHM) (unit: nm) and the full width at half maximum (FWHM) were calculated.

[0371] (External quantum efficiency EQE) The current density of the fabricated organic EL device was 10 mA / cm 2 The spectral radiance spectrum when a voltage was applied so that the value was 1 / 2 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated, assuming that Lambertian radiation was performed. Based on the measured EQE value for each example and the following formula (Equation 2X), "EQE95 (relative value)" (unit: %) was calculated. EQE (relative value) = (EQE of each example / EQE of Comparative Example 1) × 100 (number 2X)

[0372] (Life span LT95) Current density is 50mA / cm2 A voltage was applied to the organic EL device fabricated so as to satisfy the above condition, and the time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hours)) was measured as the lifetime. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Based on the measured LT95 value for each example and the following formula (Equation 3X), the "LT95 (relative value)" (unit: %) was calculated. LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100 (equation 3X)

[0373] [Table 1]

[0374] As shown in Table 1, the organic EL devices of Examples 1 and 2, which contained compound GD-A or GD-B as a compound having a structure represented by general formula (1), emitted light with higher efficiency and longer lifetime than the organic EL device of Comparative Example 1, which used comparative compound Ref-1.

[0375] <Compound evaluation> The compounds used in the preparation of the organic EL devices were evaluated as follows, and the results are shown in Table 2.

[0376] (delayed fluorescence) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 2. The compound TADF was dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. To prevent quenching by oxygen, the sample solution was frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere, creating an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of both spectra according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength absorbed by the compound TADF, there are two types of emission: prompt emission (immediate emission) that is observed immediately from the excited state, and delayed emission (delayed emission) that is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence emission means that the amount of delayed emission (delayed emission) is 5% or more of the amount of prompt emission (immediate emission). Specifically, when the amount of prompt emission (immediate emission) is X P and the amount of delay light emission is X D When X D / X P This means that the value of is 0.05 or more. The amounts of prompt luminescence and delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amounts of prompt luminescence and delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2. For the compound TADF, it was confirmed that the amount of delayed luminescence was 5% or more of the amount of prompt luminescence. Specifically, for the compound TADF, X D / X P The value was 0.05 or higher.

[0377] (Lowest excited singlet energy S1) The lowest excited singlet energy S1 was measured by the solution method described above.

[0378] (Absorption peak wavelength λ ABS ) Compound absorption peak wavelength λ ABS was measured using a spectrophotometer, model U-3310 manufactured by Hitachi High-Tech Science Corporation.

[0379] (orientation parameter S') The degree of orientation of the compound was measured by the following method. The compound was deposited on a glass substrate to a thickness of 50 nm, and spectroscopic ellipsometry measurement was performed using a spectroscopic ellipsometer. The spectroscopic ellipsometer used was an M-2000 manufactured by JA Woollam. In the spectroscopic ellipsometry measurement, the incident light was set at an angle of 45° to 75° and a wavelength of 235 nm to 1680 nm, and fitting was performed using a uniaxial anisotropy model so that the mean square error (MSE) value was 2.0 or less, and the values ​​of Psi(Ψ) and Delta(Δ) were obtained. Based on these values ​​of Psi(Ψ) and Delta(Δ), the extinction coefficient k of the glass substrate in the horizontal direction was calculated. O and the extinction coefficient k in the normal direction of the glass substrate EX Calculate the absorption peak wavelength λ ABS The extinction coefficient k O and k EX The orientation parameter S' of the compound was calculated using

[0380] (The maximum peak wavelength of the compound λ SOL and emission half width FWHM SOL ) Maximum peak wavelength λ of the compound SOL and emission half width FWHM SOL was measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum of this sample (vertical axis: emission intensity, horizontal axis: wavelength) was measured at room temperature (300 K). The peak wavelength of the emission spectrum where the emission intensity is maximum is called the maximum peak wavelength λ SOL In addition, the emission half width FWHM of the compound was calculated from the emission spectrum. SOL In this example, the emission spectrum was measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here.

[0381] [Table 2]

[0382] <Synthesis example> <Synthesis of intermediate M-1>

[0383] [ka]

[0384] Under a nitrogen atmosphere, 1-bromo-4-t-butyl-2-nitrobenzene (110 g, 427 mmol), 1-pyreneboronic acid (100 g, 406 mmol), tetrakis(triphenylphosphine)palladium(0) (14.1 g, 12.2 mmol), sodium carbonate (86 g, 813 mmol), 1,2-dimethoxyethane (900 mL), and ion-exchanged water (450 mL) were placed in a three-neck flask and heated under reflux with stirring for 4 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to yield 122 g of an orange solid. This orange solid was identified as intermediate M-1 by mass spectrometry (yield 79%).

[0385] <Synthesis of intermediate M-2>

[0386] [ka]

[0387] Under a nitrogen atmosphere, intermediate M-1 (50 g, 143 mmol), triphenylphosphine (94 g, 358 mmol), and orthodichlorobenzene (286 mL) were placed in a three-neck flask and stirred at 180 °C for 10 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by recrystallization to obtain 39.3 g of a white solid. This white solid was identified as intermediate M-2 by mass spectrometry (yield 79%).

[0388] <Synthesis of intermediate M-3>

[0389] [ka]

[0390] Under a nitrogen atmosphere, intermediate M-2 (95 g, 273 mmol), 1-bromo-2,6-difluorobenzene (185 g, 957 mmol), tripotassium phosphate (290 g, 1367 mmol), and N,N-dimethylformamide (DMF) (1367 mL) were placed in a three-neck flask and stirred at 100 °C for 10 hours. After cooling the reaction mixture to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 82.7 g of a yellow solid. This yellow solid was identified as intermediate M-3 by mass spectrometry (yield 58%).

[0391] <Synthesis of intermediate MC and intermediate MD>

[0392] [ka]

[0393] Under a nitrogen atmosphere, 4-(2-phenyl-1H-benzimidazol-1-yl)phenylboronic acid (10 g, 314 mmol), 2-bromonitrobenzene (6.4 g, 32 mmol), tetrakis(triphenylphosphine)palladium(0) (1.1 g, 1.0 mmol), sodium carbonate (6.7 g, 64 mmol), dimethoxyethane (70 mL), and water (35 mL) were placed in a three-neck flask and stirred at 80 °C for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified by silica gel column chromatography and recrystallization to obtain 8.0 g of a yellow solid. This yellow solid was identified as intermediate MC by mass spectrometry (yield: 64%).

[0394] Under a nitrogen atmosphere, intermediate MC (8.0 g, 20 mmol), triphenylphosphine (14.5 g, 55 mmol), and o-dichlorobenzene (68 mL) were placed in a three-neck flask and stirred at 160°C for 7 hours. The reaction mixture was concentrated under reduced pressure, and methanol was added. The precipitated solid was collected by filtration to obtain 3.3 g of a white solid. This white solid was identified as intermediate MD by mass spectrometry (yield 45%).

[0395] <Synthesis of intermediate ME>

[0396] [ka]

[0397] Under a nitrogen atmosphere, intermediate M-3 (4.8 g, 9.0 mmol), intermediate MD (3.3 g, 9.0 mmol), tripotassium phosphate (5.8 g, 27 mmol), and N,N-dimethylformamide (DMF) (31 mL) were placed in a three-neck flask and stirred at 100 °C for 36 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 6.0 g of a pale yellow solid. This pale yellow solid was identified as intermediate ME by mass spectrometry (yield 76%).

[0398] <Synthesis of Compound GD-A>

[0399] [ka]

[0400] Under a nitrogen atmosphere, intermediate ME (6.0 g, 7.0 mmol) and tert-butylbenzene (70 mL) were placed in a three-neck flask and cooled to -78 °C. A 1.2 mol / L sec-butyllithium solution (solvent: cyclohexane and n-hexane) (8.7 mL, 10 mmol) was added dropwise, and the mixture was heated to -40 °C and stirred for 30 min. After cooling the reaction mixture to -78 °C, boron tribromide (1.9 mL, 21 mmol) was added dropwise, and the mixture was heated to room temperature and stirred for 30 min. After cooling the reaction mixture to 0 °C, N,N-diisopropylethylamine (3.6 mL, 21 mmol) was added dropwise, and the mixture was heated to 110 °C and stirred for 1 h. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration and purified by recrystallization to obtain 0.5 g of an orange solid. This orange solid was identified as compound GD-A by mass spectrometry (yield: 9%).

[0401] <Synthesis of Intermediate MF, Intermediate MG, and Intermediate MH>

[0402] [ka]

[0403] Under a nitrogen atmosphere, N-(4-bromophenyl)benzene-1,2-diamine (10 g, 38 mmol), sodium bisulfite (6.6 g, 38 mmol), and N,N-dimethylacetamide (DMAc) (95 mL) were placed in a three-neck flask and stirred at 100 °C for 30 min. A solution of pivalaldehyde (3.3 g, 9.0 mmol) in DMAc (15 mL) was then added and stirred at 100 °C for 4 h. The reaction solution was cooled to room temperature, and 2% aqueous sodium bicarbonate solution (100 mL) was added. The precipitated solid was separated by suction filtration. 13.2 g of a white solid was obtained. This white solid was identified as intermediate MF by mass spectrometry (100% yield).

[0404] Under a nitrogen atmosphere, intermediate MF (8.9 g, 27 mmol), 2-nitrophenylboronic acid (4.5 g, 27 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.38 g, 0.54 mmol), and acetonitrile (135 mL) were placed in a three-neck flask and stirred at 90 °C for 2 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was separated, dried over sodium sulfate, and filtered. The resulting mixture was purified by silica gel chromatography to yield 6.4 g of a gray solid. This gray solid was identified as intermediate MG by mass spectrometry (yield: 59%).

[0405] [ka]

[0406] Under a nitrogen atmosphere, intermediate MG (6.4 g, 17 mmol), triphenylphosphine (12.2 g, 47 mmol), and o-dichlorobenzene (57 mL) were placed in a three-neck flask and stirred at 160°C for 2 hours. The reaction mixture was concentrated under reduced pressure, methanol was added, and the precipitated solid was collected by filtration to obtain 5.2 g of a brown solid. This brown solid was identified as intermediate MH by mass spectrometry (yield 90%).

[0407] <Synthesis of Intermediate MI> TIFF2025132789000107.tif51170

[0408] Under a nitrogen atmosphere, intermediate M-3 (7.2 g, 13 mmol), intermediate MH (4.7 g, 13 mmol), tripotassium phosphate (8.8 g, 39 mmol), and N,N-dimethylformamide (DMF) (46 mL) were placed in a three-neck flask and stirred at 100 °C for 20 hours. After cooling the reaction mixture to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 7.4 g of a pale yellow solid. This pale yellow solid was identified as intermediate MI by mass spectrometry (yield 64%).

[0409] <Synthesis of Compound GD-B>

[0410] [ka]

[0411] Under a nitrogen atmosphere, intermediate MI (7.4 g, 9.0 mmol) and t-butylbenzene (88 mL) were placed in a three-neck flask and cooled to -78 °C. A 1.2 mol / L sec-butyllithium solution (solvent: cyclohexane and n-hexane) (11 mL, 13 mmol) was added dropwise, and the mixture was heated to -40 °C and stirred for 30 min. After cooling the reaction mixture to -78 °C, boron tribromide (2.5 mL, 26 mmol) was added dropwise, and the mixture was heated to room temperature and stirred for 30 min. After cooling the reaction mixture to 0 °C, N,N-diisopropylethylamine (4.5 mL, 26 mmol) was added dropwise. The mixture was heated to 110 °C and stirred for 1 h. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration and purified by recrystallization to yield 2.0 g of an orange solid. This orange solid was identified as compound GD-B by mass spectrometry (yield: 29%).

[0412] In the above reaction scheme, DME is an abbreviation for 1,2-dimethoxyethane, PPh3 is an abbreviation for triphenylphosphine, Pd(PPh3)4 is an abbreviation for tetrakis(triphenylphosphine)palladium(0), DMF is an abbreviation for N,N-dimethylformamide, ODCB is an abbreviation for ortho-dichlorobenzene, i-Pr2NEt is an abbreviation for N,N-diisopropylethylamine, and PdCl2(amphos)2 is an abbreviation for dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II). [Explanation of symbols]

[0413] 1... organic EL element, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer.

Claims

1. A compound having a structure represented by general formula (1): 【Chemical 1】 (In the general formula (1), R １０１ ~R １２１ are each independently hydrogen atoms, halogen 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R １９０ ) a group represented by -S-(R １９１ ) 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, -C(=O)-O-(R １９２ ) a group represented by -C(=O)-N(R １９３ ) (R １９４ ) a group represented by -N(R １９５ ) (R １９６ ) a group represented by nitro group, -Si(R １９７ ) (R １９８ ) (R １９９ ) a group represented by selected from the group consisting of groups represented by the following general formula (13): R １０１ ~R １２１ At least one of the groups is a group represented by the following general formula (13): (In the compound having the structure represented by the general formula (1), R １９０ ~R １９９ 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. However, R １０１ ~R １２１ is not a substituted or unsubstituted N-carbazolyl group, The structure represented by the general formula (1) does not have a group represented by the following general formula (12): 【Chemistry 2】 (In the group represented by the general formula (12), X １ is a nitrogen atom or C—R １４１ represents X ２ is a nitrogen atom or C—R １４２ represents X ３ is a nitrogen atom or C—R １４３ represents X ４ is a nitrogen atom or C—R １４４ represents X ５ is a nitrogen atom or C—R １４５ represents R １４１ ~R １４５ 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. However, X １ ~X ５ At least one of these is represented by a nitrogen atom. * indicates the bond position.) 【Chemistry 3】 (In the group represented by the general formula (13), Y is a nitrogen atom or C—R １３５ represents R １３１ ~R １３４ one or more pairs of adjacent two or more of R １３５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. １３１ ~R １３４ 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -L １ -R １３６ is a group represented by L １ represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, R １３６ teeth, 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, * indicates the bond position.)

2. R which is not a group represented by the general formula (13) １０１ ~R １２１ 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; The compound of claim 1.

3. R １０８ , R １０９ , R １１０ and R １１１ At least one selected from the group consisting of is selected from substituents other than a hydrogen atom, 3. The compound of claim 1 or claim 2.

4. R １１０ is selected from 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, A compound according to any one of claims 1 to 3.

5. R １１５ , R １１６ , R １１７ and R １１８ At least one selected from the group consisting of is a group represented by general formula (13). A compound according to any one of claims 1 to 4.

6. R １１６ is a group represented by the general formula (13), 6. A compound according to any one of claims 1 to 5.

7. Y is C-R １３５ is expressed as 7. A compound according to any one of claims 1 to 6.

8. A light-emitting device material comprising the compound according to any one of claims 1 to 7.

9. An organic electroluminescence element, a cathode, an anode, and an organic layer between the cathode and the anode; The organic layer comprises one or more layers, At least one of the layers included in the organic layer contains the compound according to any one of claims 1 to 7 as a first compound. Organic electroluminescent element.

10. At least one layer among the layers included in the organic layer is an emitting layer, the light-emitting layer contains the first compound; The organic electroluminescence device according to claim 9 .

11. the light-emitting layer further contains a delayed fluorescent second compound; The organic electroluminescence device according to claim 10 .

12. The lowest excited singlet energy S of the second compound １ (M2) and the lowest excited singlet energy S of the first compound １ (M1) satisfies the following formula (Formula 1): The organic electroluminescence device according to claim 11 . S １ (M2)>S １ (M1)…(Number 1)

13. the light-emitting layer further contains a third compound, The lowest excited singlet energy S of the second compound １ (M2) and the lowest excited singlet energy S of the third compound １ (M3) satisfies the following formula (Formula 2): The organic electroluminescence device according to claim 12 . S １ (M3)>S １ (M2) …(number 2)

14. An electronic device equipped with the organic electroluminescence element according to any one of claims 9 to 13.

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