Compound, material for organic electroluminescence device, organic electroluminescence device and electronic device

Abstract

Provided are a compound that further improves the performance of an organic EL element, an organic electroluminescent element having further improved element performance, and an electronic device that includes such an organic electroluminescent element. A compound represented by formula (1) or formula (2) (each symbol in each formula is as defined in the specification), an organic electroluminescent element including the compound, and an electronic device including such an organic electroluminescent element.

Description

[Technical Field]

[0001] The present invention relates to a compound, a material for an organic electroluminescent device, an organic electroluminescent device, and an electronic device including the organic electroluminescent device. [Background technology]

[0002] Generally, organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") consist of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode and holes are injected from the anode into the light-emitting region. The injected electrons and holes recombine in the light-emitting region to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, the development of materials that efficiently transport electrons or holes to the light-emitting region and facilitate the recombination of electrons and holes is important for obtaining high-performance organic EL devices.

[0003] Patent Documents 1 to 17 disclose compounds used as materials for organic electroluminescence devices. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2011 / 024451 [Patent Document 2] Korean Patent Publication No. 10-2011-0064222 [Patent Document 3] U.S. Patent No. 6,110,307 [Patent Document 4] International Publication No. 2013 / 122082 [Patent Document 5] International Publication No. 2014 / 007022 [Patent Document 6] US Patent Application Publication No. 2014 / 0138633 [Patent Document 7] Korean Patent Publication No. 10-2014-0103697 [Patent Document 8] Korean Patent Publication No. 10-2015-0031892 [Patent Document 9] Korean Patent Publication No. 10-2015-0116337 [Patent Document 10] US Patent Application Publication No. 2018 / 0090688 [Patent Document 11] International Publication No. 2017 / 118238 [Patent Document 12] Korean Patent Publication No. 10-2017-0084917 [Patent Document 13] US Patent Application Publication No. 2019 / 0189927 [Patent Document 14] US Patent Application Publication No. 2020 / 0106017 [Patent Document 15] Korean Patent Publication No. 10-2018-0078177 [Patent Document 16] Korean Patent No. 10-1978651 [Patent Document 17] Korean Patent Publication No. 10-2019-0084880 Summary of the Invention [Problem to be solved by the invention]

[0005] Although many compounds for organic EL devices have been reported, there is still a demand for compounds that further improve the performance of organic EL devices.

[0006] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a compound that further improves the performance of an organic EL device, an organic EL device having further improved device performance, and an electronic device including such an organic EL device. [Means for solving the problem]

[0007] The present inventors have conducted extensive research into the performance of organic EL devices containing the compounds described in Patent Documents 1 to 17 and other compounds, and as a result have found that: a monoamine having at least one deuterium atom, in which one of the monoamines has a substituted or unsubstituted m-(9-carbazolyl)phenyl group via a specific linker (including a single bond) at the central nitrogen atom, and the remaining two monoamines have specific aryl groups or specific heterocyclic groups each bonded via a specific linker (including a single bond); or a monoamine having at least one deuterium atom, in which one of the monoamines has a substituted or unsubstituted o-(9-carbazolyl)phenyl group via a specific linker (including a single bond) at the central nitrogen atom, and the remaining two monoamines have specific aryl groups or specific heterocyclic groups each bonded via a specific linker (including a single bond); and the monoamines have at least one deuterium atom; and

[0008] In one aspect, the present invention provides a compound having at least one deuterium atom and represented by the following formula (1): [ka] (In formula (1), N * is the central nitrogen atom, Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms, Ar 1 and Ar 2 are both the substituted or unsubstituted aryl groups having 6 to 16 ring carbon atoms, the total number of carbon atoms of the two substituted or unsubstituted aryl groups having 6 to 16 ring carbon atoms is 12 to 38, L 1 represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, L 1the substituent is 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, L 2 and L 3 each independently represents a single bond, a substituted or unsubstituted non-fused arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, Ar 1 and L 2 is not cross-linked Ar 2 and L 3 is not cross-linked, R 11 ~R 14 , and R 21 ~R 28 are each independently a hydrogen atom or a substituent, and the substituent is 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.

[0009] In one embodiment, the present invention provides a compound having at least one deuterium atom and represented by the following formula (2): [ka] (In formula (2), N * is the central nitrogen atom, Ar 3 and Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (excluding a phenyl group), or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms, L 4 , L 5 and L 6 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, R 91 ~R 94 , and R101 ~R 108 are each independently a hydrogen atom or a substituent, and the substituent is Halogen atoms, nitro groups, cyano groups, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or It is a mono-, di-, or tri-substituted silyl group having a substituent selected from 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 monovalent heterocyclic group having 5 to 50 ring atoms.

[0010] In another aspect, the present invention provides a material for an organic EL device, which comprises a compound represented by the formula (1) or (2).

[0011] In still another aspect, the present invention provides an organic electroluminescence device comprising an anode, a cathode, and organic layers disposed between the anode and the cathode, wherein the organic layers comprise an emitting layer, and at least one layer of the organic layers comprises a compound represented by formula (1) or formula (2).

[0012] In still another aspect, the present invention provides an electronic device including the organic electroluminescence device. [Effects of the Invention]

[0013] An organic EL device containing a compound represented by the formula (1) or (2) exhibits improved device performance. [Brief explanation of the drawings]

[0014] [Figure 1] 1 is a schematic diagram illustrating an example of a layer structure of an organic EL element according to one embodiment of the present invention. [Figure 2] FIG. 2 is a schematic diagram showing an example of a layer structure of another organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0015] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0016] 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.

[0017] 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.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] "Substituents described herein" The substituents described in this specification will be explained below.

[0023] 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.

[0024] "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.

[0025] 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).

[0026] [ka]

[0027] [ka]

[0028] 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.

[0029] "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.

[0030] 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).

[0031] 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).

[0032] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, a triazolyl group, tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, a triazinyl group, Indolyl groups, isoindolyl groups, an indolizinyl group, a quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, a quinazolinyl group, quinoxalinyl group, benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, acridinyl group, phenazinyl group, a carbazolyl group, a benzocarbazolyl group, morpholino group, phenoxazinyl group, a phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0033] 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.

[0034] 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).

[0035] 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):

[0036] [ka]

[0037] [ka]

[0038] 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.

[0039] 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.

[0040] 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].

[0041] 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].

[0042] 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):

[0043] The above-mentioned "one or more hydrogen atoms of a monovalent heterocyclic group" means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH.

[0044] "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.

[0045] 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.

[0046] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0047] "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.

[0048] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0049] 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.

[0050] "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.

[0051] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group

[0052] "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.

[0053] 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.

[0054] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0055] -Si(R 901 )(R 902 )(R 903 ) a group represented by -Si(R 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) may be the same as or different from each other.

[0056] -O-(R 904 ) a group represented by -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0057] -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.

[0058] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0059] "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.

[0060] "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.

[0061] "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.

[0062] "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.

[0063] "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.

[0064] "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.

[0065] "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.

[0066] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0067] "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.

[0068] 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.

[0069] 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.

[0070] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0071] [ka]

[0072] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:

[0073] [ka]

[0074] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0075] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0076] [ka]

[0077] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0078] 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.

[0079] "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.

[0080] "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.

[0081] "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.

[0082] 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).

[0083] [ka]

[0084] [ka]

[0085] 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.

[0086] [ka]

[0087] 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.

[0088] [ka]

[0089] 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.

[0090] 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).

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

[0100] The above is the explanation of "substituents described in this specification."

[0101] - "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.

[0102] [ka]

[0103] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.

[0104] 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).

[0105] [ka]

[0106] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.

[0107] [ka]

[0108] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0109] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R 921 and R 922 and 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 elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by

[0110] Here, unless otherwise specified in this specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of carbon or nitrogen), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more groups" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more groups combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0111] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0112] 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 Unsubstituted heterocyclic group having 5 to 50 ring atoms and the like, a group selected from the group consisting of where R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 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 903If 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.

[0113] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and Heterocyclic groups with 5 to 50 ring atoms is a group selected from the group consisting of:

[0114] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; an aryl group having 6 to 18 ring carbon atoms, and Heterocyclic groups with 5 to 18 ring atoms is a group selected from the group consisting of:

[0115] 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."

[0116] 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.

[0117] 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.

[0118] compound The compounds of the present invention will be described below. A compound according to one embodiment of the present invention is represented by the following formula (1) and has at least one deuterium atom. However, hereinafter, the compounds of the present invention represented by formula (1) and each formula included in formula (1) described below may be simply referred to as "invention compound A." Furthermore, a compound according to one embodiment of the present invention is represented by the formula (2) below and has at least one deuterium atom. Hereinafter, the compounds of the present invention represented by the formula (2) below and formulas included in the formula (2) below may be simply referred to as "compound B of the invention." Furthermore, when referring to both "invention compound A" and "invention compound B," they may be simply referred to as "invention compounds."

[0119] Invention Compound A [ka]

[0120] The symbols in formula (1) and the formula (1) described below will be explained below. Note that the same symbols have the same meanings.

[0121] In formula (1), N * is the central nitrogen atom.

[0122] Ar 1 , Ar 2 In formula (1), Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms. Ar 1 and Ar 2 are both the substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms, the two substituted or unsubstituted aryl groups having 6 to 16 ring carbon atoms have a total of 12 to 38 carbon atoms. In this specification, the "total number of carbon atoms" includes the number of carbon atoms of substituents. Ar 1 and Ar 2 The substituents in are all unsubstituted. 1 The substitution of the substituents of Ar 2 Substitution of the substituent is not permitted.

[0123] Ar 1 and Ar 2 When the substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms represented by the formula (I) contains a substituted or unsubstituted fluorenyl group, it is preferable that at least one of the substituted or unsubstituted fluorenyl groups is represented by the following formula (A): [ka] In formula (A), R a is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, In formula (A), R b is a substituted or unsubstituted alkyl group, In formula (A), R 31 ~R 38 One of them is L 2 or L 3 is a single bond that bonds to The R that is not a single bond 31 ~R 38 are each independently a hydrogen atom or a substituent, and the substituent is the same as Ar 1 and Ar 2 The substituents and preferred embodiments are the same as those of the above.

[0124] R a and R b The details of the substituted or unsubstituted alkyl group represented by are as described above in the section "Substituents described in this specification." R a and R b The substituents of the substituted alkyl group represented by R are all unsubstituted. a and R b Substitution of the substituents of the substituted alkyl group represented by is not permitted. R a and R b The unsubstituted alkyl group represented by is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably a methyl group or a t-butyl group.

[0125] R a The details of the substituted or unsubstituted aryl group represented by are as described above in the section "Substituents described in this specification." R a The substituent of the substituted aryl group represented by R is an unsubstituted substituent. a Substitution of the substituents of the substituted aryl group represented by is not permitted. R a The unsubstituted aryl group represented by is more preferably selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a phenanthryl group.

[0126] Ar 1 and Ar 2 An aryl group represented by Ar1 and Ar 2 The details of the substituted or unsubstituted aryl group having 6 to 16 ring carbon atoms represented by are as described above in the section "Substituents described in this specification." Ar 1 and Ar 2 The unsubstituted aryl group represented by the formula (I) preferably consists of only a benzene ring, and more preferably is selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a phenanthryl group.

[0127] Ar 1 and Ar 2 Heterocyclic group represented by Ar 1 and Ar 2 The details of the substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms represented by are as described above in the section "Substituents described in this specification." Ar 1 and Ar 2 is preferably a heterocyclic group selected from 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, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, and a naphthobenzothiophenyl group, and more preferably a heterocyclic group selected from a pyridyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0128] Ar 1 and Ar 2 Substituents of Ar 1 and Ar 2 The substituents in each independently represent: Halogen atoms, nitro groups, cyano groups, 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 haloalkyl group having 1 to 50 carbon atoms; an unsubstituted alkoxy group having 1 to 50 carbon atoms; an unsubstituted haloalkoxy group having 1 to 50 carbon atoms, an unsubstituted alkylthio group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms; an unsubstituted aryloxy group having 6 to 50 ring carbon atoms, an unsubstituted arylthio group having 6 to 50 ring carbon atoms, an unsubstituted aralkyl group having 7 to 50 carbon atoms; an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or The silyl group is a mono-, di-, or tri-substituted silyl group having a substituent selected from an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0129] halogen atoms Ar 1 and Ar 2 The details of the halogen atom as a substituent of are as described above in the section "Substituents described in this specification."

[0130] Alkyl group Ar 1 and Ar 2 The details of the unsubstituted alkyl group having 1 to 50 carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0131] Alkenyl group Ar 1 and Ar 2 Details of the unsubstituted alkenyl group having 2 to 50 carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0132] Alkynyl group Ar 1and Ar 2 Details of the unsubstituted alkynyl group having 2 to 50 carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0133] cycloalkyl group Ar 1 and Ar 2 Details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0134] Haloalkyl groups Ar 1 and Ar 2 Details of the unsubstituted haloalkyl group having 1 to 50 carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0135] alkoxy group Ar 1 and Ar 2 Details of the unsubstituted alkoxy group having 1 to 50 carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0136] Haloalkoxy group Ar 1 and Ar 2 The unsubstituted haloalkoxy group having 1 to 50 carbon atoms as a substituent of the above is a group represented by -O(G12), where G12 is the unsubstituted haloalkyl group.

[0137] Alkylthio group Ar 1 and Ar 2 Details of the unsubstituted alkylthio group having 1 to 50 carbon atoms as the substituent of are as described above in the section "Substituents described in this specification."

[0138] aryl group Ar 1 and Ar 2Details of the unsubstituted aryl group having 6 to 50 ring carbon atoms as the substituent of are as described above in the section "Substituents described in this specification." Ar 1 and Ar 2 The unsubstituted aryl group as a substituent of is more preferably selected from the group consisting of a phenyl group, a naphthyl group, and a phenanthryl group. However, Ar 1 and Ar 2 The unsubstituted aryl group having 6 to 50 ring carbon atoms as a substituent in the above includes, for example, fused aryl groups such as a fluorenyl group, a phenanthryl group, and an anthracenyl group; but does not include ring assemblies such as a biphenyl group, a terphenyl group, and a naphthylphenyl group.

[0139] aryloxy group Ar 1 and Ar 2 Details of the unsubstituted aryloxy group having 6 to 50 ring carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0140] arylthio group Ar 1 and Ar 2 Details of the unsubstituted arylthio group having 6 to 50 ring carbon atoms as the substituent of are as described above in the section "Substituents described in this specification."

[0141] Aralkyl groups Ar 1 and Ar 2 Details of the unsubstituted aralkyl group having 7 to 50 carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0142] heterocyclic group Ar 1 and Ar 2 Details of the unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms as the substituent of are as described above in the section "Substituents described in this specification."

[0143] Substituted Silyl Groups Ar 1 and Ar 2 The details of the substituents of the mono-, di- or tri-substituted silyl group as the substituent of are as described above in the section "Substituents described in this specification."

[0144] L 1 In formula (1), L 1 represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0145] L 1 An arylene group represented by L 1 The details of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by are as described above in the section "Substituents described in this specification." L 1 The substituted or unsubstituted arylene group represented by is preferably a phenylene group, a biphenylene group or a terphenylene group.

[0146] L 1 Heterocyclic group represented by L 1 The details of the substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by are as described above in the section "Substituents described in this specification."

[0147] L 1 Substituents of L 1 The substituent is 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.

[0148] Alkyl group L 1 The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0149] aryl group L 1 The details of the pre-substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms as the substituent are as described above in the section "Substituents described in this specification."

[0150] L 2 , L 3 In formula (1), L 2 and L 3 are each independently a single bond, a substituted or unsubstituted non-fused arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0151] In formula (1), Ar 1 and L 2 is not cross-linked, and Ar 2 and L 3 does not crosslink.

[0152] L 2 and L 3 A non-fused arylene group represented by L 2 and L 3 The details of the substituted or unsubstituted non-fused arylene group having 6 to 30 ring carbon atoms represented by are non-fused groups selected from those described above in the section "Substituents described in this specification." L 2 and L 3 The unsubstituted non-condensed arylene group represented by the formula (I) is preferably a phenylene group, a biphenylene group, or a terphenylene group.

[0153] L 2 and L 3 Heterocyclic group represented by L 2 and L 3 The details of the substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by are as described above in the section "Substituents described in this specification."

[0154] L 2and the substituents of L 3 Substituents of L 2 and the substituents of L 3 The substituents are each independently the same as Ar 1 and Ar 2 The substituents and preferred embodiments are the same as those of the above.

[0155] R 11 ~R 14 , R 21 ~R 28 In formula (1), R 11 ~R 14 , and R 21 ~R 28 are each independently a hydrogen atom or a substituent, and the substituent is L 1 The substituents and preferred embodiments are the same as those of the above.

[0156] Structural formula of a preferred example of the invention compound A Suitable examples of invention compound A include compounds represented by the following formulae (1-1) to (1-10): The compounds represented by formulae (1-1) to (1-10) have at least one deuterium atom.

[0157] [ka]

[0158] In formula (1-1), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0159] In formula (1-1), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0160] In formula (1-1), R 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 are each independently a hydrogen atom or a substituent, and the substituent is the same as Ar 1 and Ar 2 is the same substituent as the substituent of however, R 131 ~R 135 is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 the other one or two selected from are single bonds bonded to *r, R 171 ~R 175 One selected from *p 1 is a single bond that connects to R 181 ~R 186 One selected from *q 1 is a single bond that connects to R 181 ~R 186 The other one or two selected from *r 1 is a single bond that bonds to

[0161] In formula (1-1), m1, m11, and m21 each independently represent 0 or 1, and n1, n11, and n21 each independently represent 0 or 1. When m1 is 0 and n1 is 0, *r is a nitrogen atom N * binds to When m1 is 0 and n1 is 1, *p is a nitrogen atom N * binds to When m1 is 1 and n1 is 0, R 131 ~R 135 is a single bond bonded to *r, When m11 is 0 and n11 is 0, *r 1 is a nitrogen atom N * binds to When m11 is 0 and n11 is 1, *p 1 is a nitrogen atom N * binds to When m11 is 1 and n11 is 0, R 171 ~R 175 One of the following is selected: 1 is a single bond that connects to When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that connects to k and k1 are each independently 1 or 2.

[0162] In formula (1-1), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166two adjacent R's selected from the above, which are not single bonds 171 ~R 175 two adjacent R's selected from the above, which are not single bonds 181 ~R 186 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from, and R 191 ~R 195 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A1 and the benzene ring B1, the benzene ring A1 and the benzene ring C1, the benzene ring B1 and the benzene ring C1, the benzene ring A2 and the benzene ring B2, the benzene ring A2 and the benzene ring C2, the benzene ring B2 and the benzene ring C2, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0163] [ka]

[0164] In formula (1-2), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0165] In formula (1-2), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0166] In formula (1-2), R 131 ~R 135 , R 141 ~R 146 , R 81 ~R 85 , R 51 ~R 55 and R 61 ~R 68 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 131 ~R 135 is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 the other one or two selected from are single bonds bonded to *r, R 81 ~R 85 One selected from is a single bond bonded to *c.

[0167] In formula (1-2), m1 and m21 each independently represent 0 or 1, and n1 and n21 each independently represent 0 or 1. When m1 is 0 and n1 is 0, *r is a nitrogen atom N * binds to When m1 is 0 and n1 is 1, *p is a nitrogen atom N * binds to When m1 is 1 and n1 is 0, R 131 ~R 135 is a single bond bonded to *r, When m21 is 0 and n21 is 0, *r 2is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that connects to k is 1 or 2.

[0168] In formula (1-2), R 61 ~R 68 is a single bond bonded to *f, m2 is 0 or 1, and when m2 is 0, *c is a nitrogen atom N * Combine with.

[0169] In formula (1-2), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 81 ~R 85 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from, and R 61 ~R 68 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A1 and the benzene ring B1, the benzene ring A1 and the benzene ring C1, the benzene ring B1 and the benzene ring C1, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0170] [ka]

[0171] In formula (1-3), R 11 ~R14 and R 21 ~R 28 is as mentioned above.

[0172] In formula (1-3), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0173] In formula (1-3), R 131 ~R 135 , R 141 ~R 146 , R 81 ~R 85 , R 41 ~R 46 , R 51 ~R 55 and R 71 ~R 80 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 131 ~R 135is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 the other one or two selected from are single bonds bonded to *r, R 81 ~R 85 is a single bond bonded to *c, R 41 ~R 46 is a single bond bonded to *d, and R 41 ~R 46 The other one selected from is a single bond bonded to *e.

[0174] In formula (1-3), m1, m3, and m21 each independently represent 0 or 1, and n1, n3, and n21 each independently represent 0 or 1. When m1 is 0 and n1 is 0, *r is a nitrogen atom N * binds to When m1 is 0 and n1 is 1, *p is a nitrogen atom N * binds to When m1 is 1 and n1 is 0, R 131 ~R 135 is a single bond bonded to *r, When m3 is 0 and n3 is 0, *e is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 81 ~R 85 is a single bond bonded to *e, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected:2 is a single bond that connects to k is 1 or 2.

[0175] In formula (1-3), R 71 ~R 80 One selected from is a single bond bonded to *h.

[0176] In formula (1-3), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from, and R 71 ~R 80 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and benzene ring A1 and benzene ring B1, benzene ring A1 and benzene ring C1, benzene ring B1 and benzene ring C1, benzene ring A12 and benzene ring B12, and benzene ring A3 and benzene ring B3 are not bridged.

[0177] [ka]

[0178] In formula (1-4), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0179] In formula (1-4), R 151 ~R 155 and R161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0180] In formula (1-4), R 131 ~R 135 , R 141 ~R 146 , R 31 ~R 35 , R 51 ~R 55 and R 121 ~R 128 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 131 ~R 135 is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 the other one or two selected from are single bonds bonded to *r, R 31 ~R35 is a single bond bonded to *c, R 121 ~R 128 One selected from is a single bond bonded to *t.

[0181] In formula (1-4), m1 and m21 each independently represent 0 or 1, and n1 and n21 each independently represent 0 or 1. When m1 is 0 and n1 is 0, *r is a nitrogen atom N * binds to When m1 is 0 and n1 is 1, *p is a nitrogen atom N * binds to When m1 is 1 and n1 is 0, R 131 ~R 135 is a single bond bonded to *r, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that connects to k is 1 or 2.

[0182] In formula (1-4), m7 is 0 or 1, and when m7 is 0, *c is a nitrogen atom N * Combine with.

[0183] In formula (1-4), Y is an oxygen atom, a sulfur atom, or CR c R d and R c and R d are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. c and R d When both of R are aryl groups, R c and Rd They may be linked together to form a spiro ring.

[0184] In formula (1-4), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 31 ~R 35 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from 121 ~R 124 and R 125 ~R 128 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A1 and the benzene ring B1, the benzene ring A1 and the benzene ring C1, the benzene ring B1 and the benzene ring C1, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0185] [ka]

[0186] In formula (1-5), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0187] In formula (1-5), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0188] In formula (1-5), R 81 ~R 85 , R 281 ~R 285 , R 61 ~R 68 and R 261 ~R 268 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. However, R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 281 ~R 285 One of the following is selected: 2 is a single bond that connects to R 61 ~R 68 is a single bond bonded to *f, R 261 ~R 268 One of the following is selected: 1 is a single bond that bonds to

[0189] In formula (1-5), m21 is 0 or 1, n21 is 0 or 1, When m21 is 0 and n21 is 0, *r 2is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0190] In formula (1-5), m2 is 0 or 1, and when m2 is 0, *c 1 is a nitrogen atom N * and m12 is 0 or 1, and when m12 is 0, *c 2 is a nitrogen atom N * Combine with.

[0191] In formula (1-5), R 81 ~R 85 two adjacent R's selected from the group consisting of 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 281 ~R 285 Two adjacent ones selected from R 61 ~R 68 and R 261 ~R 268 adjacent two selected from the above are each independently not bonded to each other, and therefore do not form a ring structure, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0192] [ka]

[0193] In formula (1-6), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0194] In formula (1-6), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0195] In formula (1-6), R 81 ~R 85 , R 281 ~R 285 , R 41 ~R 46 , R 61 ~R 68 and R 71 ~R 80 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. However, R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 281 ~R 285 One of the following is selected: 2 is a single bond that connects to R 41 ~R46 is a single bond bonded to *d, and R 41 ~R 46 is a single bond bonded to *e, R 61 ~R 68 is a single bond bonded to *f, R 71 ~R 80 One selected from is a single bond bonded to *h.

[0196] In formula (1-6), m21 and m3 each independently represent 0 or 1, and n21 and n3 each independently represent 0 or 1. When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that connects to When m3 is 0 and n3 is 0, *e is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c 2 is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 281 ~R 285 One selected from is a single bond bonded to *e.

[0197] In formula (1-6), m2 is 0 or 1, and when m2 is 0, *c 1 is a nitrogen atom N * Combine with.

[0198] In formula (1-6), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 151 ~R 155two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 281 ~R 285 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 Two adjacent ones selected from R 61 ~R 68 two adjacent ones selected from, and R 71 ~R 80 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A22 and the benzene ring B22, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0199] [ka]

[0200] In formula (1-7), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0201] In formula (1-7), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0202] In formula (1-7), R 81 ~R 85 , R 31 ~R 35 , R 61 ~R 68 and R 121 ~R 128 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. However, R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 31 ~R 35 One of the following is selected: 2 is a single bond that connects to R 61 ~R 65 is a single bond bonded to *f, and R 121 ~R 128 One selected from is a single bond bonded to *t.

[0203] In formula (1-7), m21 is 0 or 1, n21 is 0 or 1, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0204] In formula (1-7), m2 is 0 or 1, and when m2 is 0, *c 1is a nitrogen atom N * and m7 is 0 or 1, and when m7 is 0, *c 2 is a nitrogen atom N * Combine with.

[0205] In formula (1-7), Y is an oxygen atom, a sulfur atom, or CR c R d and R c and R d are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. c and R d When both of R are aryl groups, R c and R d They may be linked together to form a spiro ring.

[0206] In formula (1-7), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 31 ~R 35 Two adjacent ones selected from R 61 ~R 68 and R 121 ~R 128 adjacent two selected from the above are each independently not bonded to each other, and therefore do not form a ring structure, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0207] [ka]

[0208] In formula (1-8), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0209] In formula (1-8), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0210] In formula (1-8), R 81 ~R 85 , R 41 ~R 46 , R 281 ~R 285 , R 241 ~R 246 , R 71 ~R 80 and R 271 ~R 280 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 41 ~R46 One selected from *d 1 is a single bond that connects to R 41 ~R 46 The other one selected from *e 1 is a single bond that connects to R 281 ~R 285 One of the following is selected: 2 is a single bond that connects to R 241 ~R 246 One selected from *d 2 is a single bond that connects to R 241 ~R 246 The other one selected from *e 2 is a single bond that connects to R 71 ~R 80 One selected from *h 1 is a single bond that connects to R 271 ~R 280 One selected from *h 2 is a single bond that bonds to

[0211] In formula (1-8), m3, m13, and m21 each independently represent 0 or 1, and n3, n13, and n21 each independently represent 0 or 1. When m3 is 0 and n3 is 0, *e 1 is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c 1 is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 81 ~R 85 One selected from *e 1 is a single bond that connects to When m13 is 0 and n13 is 0, *e 2 is a nitrogen atom N * binds to When m13 is 0 and n13 is 1, *c 2 is a nitrogen atom N * binds to When m13 is 1 and n13 is 0, R 281 ~R285 One selected from *e 2 is a single bond that connects to When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0212] In formula (1-8), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 281 ~R 285 Two adjacent ones selected from R 241 ~R 246 Two adjacent ones selected from R 71 ~R 80 two adjacent ones selected from, and R 271 ~R 280 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A12 and the benzene ring B12, the benzene ring A22 and the benzene ring B22, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0213] [ka] In formula (1-9), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0214] In formula (1-9), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0215] In formula (1-9), R 81 ~R 85 , R 41 ~R 46 , R 31 ~R 35 , R 71 ~R 80 and R 121 ~R 128 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 41 ~R 46 is a single bond bonded to *d, and R 41~R 46 is a single bond bonded to *e, R 31 ~R 35 One of the following is selected: 2 is a single bond that connects to R 71 ~R 80 is a single bond bonded to *h, R 121 ~R 128 One selected from is a single bond bonded to *t.

[0216] In formula (1-9), m3 and m21 each independently represent 0 or 1, and n3 and n21 each independently represent 0 or 1. When m3 is 0 and n3 is 0, *e is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c 1 is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 81 ~R 85 is a single bond bonded to *e, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0217] In formula (1-9), m7 is 0 or 1, and when m7 is 0, *c 2 is a nitrogen atom N * Combine with.

[0218] In formula (1-9), Y is an oxygen atom, a sulfur atom, or CR c R d and R c and Rd are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, provided that R c and R d and (b) are substituted or unsubstituted aryl groups having 6 to 50 ring carbon atoms.

[0219] In formula (1-9), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 31 ~R 35 Two adjacent ones selected from R 71 ~R 80 two adjacent ones selected from, and R 121 ~R 128 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A12 and the benzene ring B12, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0220] [ka] In formula (1-10), R 11 ~R 14 and R 21 ~R 28 is as mentioned above.

[0221] In formula (1-10), R 151 ~R 155 and R 161 ~R 166 are each independently a hydrogen atom, 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. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that bonds to

[0222] In formula (1-10), R 31 ~R 35 , R 231 ~R 235 , R 121 ~R 128 and R 321 ~R 328 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 31 ~R 35 One of the following is selected: 1 is a single bond that connects to R 231 ~R 235 One of the following is selected: 2 is a single bond that connects to R 121 ~R 128 One selected from *t 1 is a single bond that connects to R 321 ~R 328 One selected from *t 2 is a single bond that bonds to

[0223] In formula (1-10), each m21 independently represents 0 or 1, and each n21 independently represents 0 or 1. When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0224] In formula (1-10), m7 is 0 or 1, and when m7 is 0, *c 1 is a nitrogen atom N * and m17 is 0 or 1, and when m17 is 0, *c 2 is a nitrogen atom N * Combine with.

[0225] In formula (1-10), Y 1 and Y 2 are each independently an oxygen atom, a sulfur atom, or CR c R d and R c and R d are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. c and R d When both of R are aryl groups, R c and R d They may be linked together to form a spiro ring.

[0226] In formula (1-10), R 31 ~R 35 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166two adjacent R's selected from the above, which are not single bonds 231 ~R 235 Two adjacent ones selected from R 121 ~R 128 and R 321 ~R 328 adjacent two selected from the above are each independently not bonded to each other, and therefore do not form a ring structure, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0227] (Deuterium atom possessed by invention compound A) Invention compound A contains at least one deuterium atom. Deuterium atoms may be intentionally introduced into Compound A of the invention by using deuterated compounds as some or all of the starting compounds. Here, examples of the partially or completely deuterated raw material compound include a compound that forms a 9-carbazolyl group in formula (1), a compound that forms a phenylene group in formula (1), a compound that forms a linker (L 1 , L 2 , L 3 ), a compound forming the terminal (Ar 1 , Ar 2 ), and compounds that form

[0228] In formula (1), L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 11 ~R14 and R 21 ~R 28 It is preferred that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in the following formula (1-11), the sum of a, b, c, d, e, f, and g is preferably 1 or more. [ka] In the formula (1-11), "Da" is R 21 ~R 28 indicates that a hydrogen atoms are deuterium atoms, and "Db" indicates that R 11 ~R 14 indicates that b hydrogen atoms are deuterium atoms, and "Dc" indicates that L 1 "Dd" indicates that c hydrogen atoms directly bonded to the arylene group or divalent heterocyclic group represented by Ar 2 "De" indicates that d hydrogen atoms directly bonded to the aryl group or monovalent heterocyclic group represented by the formula (I) are deuterium atoms. 3 "Df" indicates that e hydrogen atoms directly bonded to the non-fused arylene group or divalent heterocyclic group represented by the formula (I) are deuterium atoms. 2 "Dg" indicates that f of the hydrogen atoms directly bonded to the non-fused arylene group or divalent heterocyclic group represented by Ar 1 indicates that g of the hydrogen atoms directly bonded to the aryl group or monovalent heterocyclic group represented by the formula (I) are deuterium atoms.

[0229] Furthermore, in formula (1), at least one deuterium atom contained in the invention compound A is L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 11 ~R 14 and R 21 ~R 28 (i.e., in formula (1), Ar 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R 14 and R 21 ~R 28 When is substituted, the substituent preferably does not contain a deuterium atom.

[0230] In formula (1), L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 11 ~R 14 and R 21 ~R 28 It is preferred that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in formula (1-11), the sum of a, b, c, d, e, and f is preferably 1 or more.

[0231] Furthermore, in formula (1), at least one deuterium atom contained in the invention compound A is L 1a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 11 ~R 14 and R 21 ~R 28 (i.e., in formula (1), Ar 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R 14 and R 21 ~R 28 When Ar is substituted, the substituent does not contain a deuterium atom, and Ar 1 A hydrogen atom directly bonded to the aryl group represented by Ar 1 It is more preferable that the hydrogen atom directly bonded to the monovalent heterocyclic group represented by does not include a deuterium atom.

[0232] In formula (1), L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by11 ~R 14 It is more preferable that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in formula (1-11), the sum of b, c, d, e, f, and g is preferably 1 or more.

[0233] Furthermore, in formula (1), at least one deuterium atom contained in the invention compound A is L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by 11 ~R 14 (i.e., in formula (1), Ar 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R 14 and R 21 ~R 28 When R is substituted, the substituent does not contain a deuterium atom, and 21 ~R 28 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0234] In formula (1), L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 A hydrogen atom directly bonded to a divalent heterocyclic group represented by 11 ~R 14 It is preferred that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in formula (1-11), the sum of b, c, e, and f is preferably 1 or more.

[0235] Furthermore, in formula (1), at least one deuterium atom contained in the invention compound A is L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 A hydrogen atom directly bonded to a divalent heterocyclic group represented by 11 ~R 14 (i.e., in formula (1), Ar 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R 14 and R 21 ~R 28 When Ar is substituted, the substituent does not contain a deuterium atom, and Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by 21 ~R 28 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0236] In formula (1), L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by 2 At least one of the hydrogen atoms directly bonded to the monovalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (1-11), the sum of c, d, e, f, and g is preferably 1 or more.

[0237] Furthermore, in formula (1), at least one deuterium atom contained in invention compound A is L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by 2 and at least one hydrogen atom directly bonded to a monovalent heterocyclic group represented by 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R 14 and R 21 ~R 28 When R is substituted, the substituent does not contain a deuterium atom, and 11 ~R 14The hydrogen atom and R 21 ~R 28 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0238] In formula (1), L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 At least one of the hydrogen atoms directly bonded to the divalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (1-11), the sum of c, e, and f is preferably 1 or more.

[0239] Furthermore, in formula (1), at least one deuterium atom contained in invention compound A is L 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 and at least one hydrogen atom directly bonded to a divalent heterocyclic group represented by 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R 14 and R 21 ~R 28 When Ar is substituted, the substituent does not contain a deuterium atom, and Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 11 ~R 14 and R 21 ~R 28 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0240] In formula (1), L 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by 2 At least one of the hydrogen atoms directly bonded to the monovalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (1-11), the sum of d, e, f and g is preferably 1 or more.

[0241] Furthermore, in formula (1), at least one deuterium atom contained in invention compound A is L 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1 A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by 2 and at least one hydrogen atom directly bonded to a monovalent heterocyclic group represented by 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R14 and R 21 ~R 28 When L is substituted, the substituent does not contain a deuterium atom, and 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to a divalent heterocyclic group represented by R 11 ~R 14 and R 21 ~R 28 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0242] In formula (1), L 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 At least one of the hydrogen atoms directly bonded to the divalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (1-11), the sum of e and f is preferably 1 or more.

[0243] Furthermore, in formula (1), at least one deuterium atom contained in invention compound A is L 2 a hydrogen atom directly bonded to the non-fused arylene group represented by 2 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 3 a hydrogen atom directly bonded to the non-fused arylene group represented by 3 and at least one hydrogen atom directly bonded to a divalent heterocyclic group represented by 1 ,Ar 2 ,L 1 ~L 3 ,R 11 ~R 14 and R 21 ~R 28 When L is substituted, the substituent does not contain a deuterium atom, and 1 a hydrogen atom directly bonded to the arylene group represented by 1 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 1A hydrogen atom directly bonded to an aryl group represented by Ar 1 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 2 A hydrogen atom directly bonded to an aryl group represented by Ar 2 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 11 ~R 14 and R 21 ~R 28 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0244] The deuteration rate of invention compound A depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain proportion of naturally occurring proton isotopes may be contained. Therefore, the deuteration rate of invention compound A shown below includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the proportion determined simply by counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of invention compound A is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and particularly preferably 50% or more.

[0245] Invention compound A may be a mixture containing a deuterated compound (a compound into which deuterium atoms have been intentionally introduced) and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture (the ratio of the number of deuterium atoms to the total number of hydrogen atoms in invention compound A contained in the mixture) is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and particularly preferably 50% or more and less than 100%.

[0246] The invention compound A is L 1 ~L 3 and R 11 ~R 14 The ratio of the number of deuterium atoms to the total number of hydrogen atoms is preferably 10% or more, more preferably 20% or more, even more preferably 30% or more, still more preferably 40% or more, and particularly preferably 50% or more.

[0247] Suitable examples of invention compound A include compounds represented by the following formulae (1-11-1) to (1-11-16).

[0248] [ka] (In formula (1-11-1), x+y+z+k+l+m+n=1 to 34, and each R is omitted.)

[0249] [ka] (In formula (1-11-2), x+y+z+k+l+m+n=1 to 34, and each R is omitted.)

[0250] [ka] (In formula (1-11-3), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0251] [ka] (In formula (1-11-4), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0252] [ka] (In formula (1-11-5), x+y+z+k+l+m+n+o=1 to 38, and each R is omitted.)

[0253] [ka] (In formula (1-11-6), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0254] [ka] (In formula (1-11-7), x+y+z+k+l+m+n=1 to 38, and each R is omitted.)

[0255] [ka] (In formula (1-11-8), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0256] [ka] (In formula (1-11-9), x+y+z+k+l+m=1 to 43, and each R is omitted.)

[0257] [ka] (In formula (1-11-10), x+y+z+k+l+m+n+o=1 to 38, and each R is omitted.)

[0258] [ka] (In formula (1-11-11), x+y+z+k+l+m+n=1 to 38, and each R is omitted.)

[0259] [ka] (In formula (1-11-12), x+y+z+k+l+m+n=1 to 42, and each R is omitted.)

[0260] [ka] (In formula (1-11-13), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0261] [ka] (In formula (1-11-14), x+y+z+k+l+m+n=1 to 34, and each R is omitted.)

[0262] [ka] (In equation (1-11-15), x+y+z+k+l+m=1 to 32, and each R is omitted.)

[0263] [ka] (In formula (1-11-16), x+y+z+k+l+m+n+o=1 to 38, and each R is omitted.)

[0264] Unless otherwise specified, details of the substituents (optional substituents) in the case of "substituted or unsubstituted" included in the definition of each formula above are as described in the section "Substituents in the case of 'substituted or unsubstituted'".

[0265] Compound A of the invention can be easily produced by a person skilled in the art by referring to the synthesis examples below and known synthesis methods.

[0266] Invention Compound B A compound according to one aspect of the present invention is represented by the following formula (2). [ka]

[0267] The symbols in formula (2) and each formula contained in formula (2) described below will be explained below. Note that the same symbols have the same meaning.

[0268] In formula (2), N * is the central nitrogen atom.

[0269] Ar3 , Ar 4 In formula (2), Ar 3 and Ar 4 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (excluding a phenyl group), or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.

[0270] Ar 3 and Ar 4 An aryl group represented by (excluding phenyl groups) Ar 3 and Ar 4 The details of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (excluding phenyl group) represented by are as described above in the section "Substituents described in this specification." Ar 3 and Ar 4 The substituted or unsubstituted aryl group (excluding phenyl group) having 6 to 30 ring carbon atoms represented by the formula (I) is preferably a substituted or unsubstituted aryl group having 10 to 30 ring carbon atoms, and more preferably a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzanthryl group, an aceanthryl group, a phenanthryl group, a benzo[c]phenanthryl group, a phenalenyl group, or a fluorenyl group.

[0271] Ar 3 and Ar 4 Heterocyclic group represented by Ar 3 and Ar 4 The details of the substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms represented by are as described above in the section "Substituents described in this specification." Ar 3 and Ar 4is preferably a heterocyclic group selected from 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, a dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, and a naphthobenzothiophenyl group, and more preferably a heterocyclic group selected from a pyridyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0272] L 4 , L 5 , L 6 In formula (2), L 4 , L 5 and L 6 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0273] L 4 , L 5 and L 6 An arylene group represented by L 4 , L 5 and L 6 The details of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by the formula (I) are as described above in the section "Substituents described in this specification." L 4 , L 5 and L 6 The unsubstituted arylene group represented by the formula (I) is preferably a phenylene group, a biphenylene group, or a terphenylene group.

[0274] L 4 , L 5 and L 6 Heterocyclic group represented by L 4 , L 5 and L 6The details of the substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by are as described above in the section "Substituents described in this specification."

[0275] Ar 3 The substituents of Ar 4 The substituents of L 4 The substituents of L 5 and L 6 Substituents of Ar 3 The substituents of Ar 4 The substituents of L 4 The substituents of L 5 and L 6 The substituents are each independently the same as Ar 1 The substituents of Ar 2 The substituents of L 1 The substituents of L 2 and L 3 The substituents and preferred embodiments are the same as those of the above.

[0276] R 91 ~R 94 , R 101 ~R 108 In formula (2), R 91 ~R 94 , and R 101 ~R 108 are each independently a hydrogen atom or a substituent, and the substituent is Halogen atoms, nitro groups, cyano groups, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or The silyl group is a mono-, di-, or tri-substituted silyl group having a substituent selected from 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 monovalent heterocyclic group having 5 to 50 ring atoms.

[0277] halogen atoms R 91 ~R 94 , and R 101 ~R 108 The details of the halogen atom represented by are as described above in the section "Substituents described in this specification."

[0278] Alkyl group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0279] Alkenyl group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0280] Alkynyl group R 91 ~R94 , and R 101 ~R 108 The details of the substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0281] cycloalkyl group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0282] Haloalkyl groups R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0283] alkoxy group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0284] Haloalkoxy group R 91 ~R 94 , and R 101 ~R 108 The substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms represented by the formula (I) is a group represented by -O(G12), where G12 is the substituted or unsubstituted haloalkyl group.

[0285] Alkylthio group R 91 ~R 94 , and R 101 ~R 108The details of the substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0286] aryl group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0287] aryloxy group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms represented by the formula (I) are as described above in the section "Substituents described in this specification."

[0288] arylthio group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms represented by the formula (I) are as described above in the section "Substituents described in this specification."

[0289] Aralkyl groups R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms represented by are as described above in the section "Substituents described in this specification."

[0290] heterocyclic group R 91 ~R 94 , and R 101 ~R 108 The details of the substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms represented by are as described above in the section "Substituents described in this specification."

[0291] Substituted Silyl Groups R 91 ~R 94 , and R 101 ~R 108 Details of the substituents of the mono-, di- or tri-substituted silyl group represented by are as described above in the section "Substituents described in this specification."

[0292] Structural formula of preferred examples of invention compound B Suitable examples of invention compound B include compounds represented by the following formulae (2-1) to (2-10): The compounds represented by formulae (2-1) to (2-10) have at least one deuterium atom.

[0293] [ka]

[0294] In formula (2-1), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0295] In formula (2-1), R 151 ~R 155 , R 161 ~R 166 , R 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 , and R 191 ~R 195 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 131 ~R 135 is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 is a single bond bonded to *r, R 171 ~R 175 One selected from *p 1 is a single bond that connects to R 181 ~R 186 One selected from *q 1 is a single bond that connects to R 181 ~R 186 The other one selected from *r 1 is a single bond that bonds to

[0296] In formula (2-1), m1, m11, and m21 each independently represent 0 or 1, and n21 represents 0 or 1. When m1 is 0, *p is a nitrogen atom N * binds to When m11 is 0, *p 1 is a nitrogen atom N * binds to When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0297] In formula (2-1), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 171 ~R 175 two adjacent R's selected from the above, which are not single bonds 181 ~R 186 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from, and R 191 ~R 195 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A1 and the benzene ring B1, the benzene ring B1 and the benzene ring C1, the benzene ring A2 and the benzene ring B2, the benzene ring B2 and the benzene ring C2, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0298] [ka]

[0299] In formula (2-2), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0300] In formula (2-2), R 151 ~R 155 , R161 ~R 166 , R 131 ~R 135 , R 141 ~R 146 , R 81 ~R 85 , R 51 ~R 55 and R 61 ~R 68 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 131 ~R 135 is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 is a single bond bonded to *r, R 81 ~R 85 is a single bond bonded to *c, R 61 ~R 68 One selected from is a single bond bonded to *f.

[0301] In formula (2-2), m1, m2, and m21 each independently represent 0 or 1, and n21 represents 0 or 1. When m1 is 0, *p is a nitrogen atom N * binds to When m2 is 0, *c is a nitrogen atom N * binds to When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0302] In formula (2-2), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 81 ~R 85 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from, and R 61 ~R 68 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A1 and the benzene ring B1, the benzene ring B1 and the benzene ring C1, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0303] [ka]

[0304] In formula (2-3), R 91~R 94 and R 101 ~R 108 is as mentioned above.

[0305] In formula (2-3), R 151 ~R 155 , R 161 ~R 166 , R 131 ~R 135 , R 141 ~R 146 , R 81 ~R 85 , R 41 ~R 46 , R 51 ~R 55 and R 71 ~R 80 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 131 ~R 135 is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 is a single bond bonded to *r, R 81 ~R 85 is a single bond bonded to *c, R 41 ~R 46 is a single bond bonded to *d, and R 41 ~R 46 is a single bond bonded to *e, R 71 ~R 80 One selected from is a single bond bonded to *h.

[0306] In formula (2-3), m1, m3, and m21 each independently represent 0 or 1, and n3 and n21 each independently represent 0 or 1. When m1 is 0, *p is a nitrogen atom N * binds to When m3 is 0 and n3 is 0, *e is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 81 ~R 85 is a single bond bonded to *e, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0307] In formula (2-3), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from, and R 71 ~R 80 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A1 and the benzene ring B1, the benzene ring B1 and the benzene ring C1, the benzene ring A12 and the benzene ring B12, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0308] [ka]

[0309] In formula (2-4), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0310] In formula (2-4), R 151 ~R 155 , R 161 ~R 166 , R 131 ~R 135 , R 141 ~R 146 , R 31 ~R 35 , R 51 ~R 55 , and R 121 ~R 128 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55and R 191 ~R 195 The same applies to the preferred embodiments. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 131 ~R 135 is a single bond bonded to *p, R 141 ~R 146 is a single bond bonded to *q, and R 141 ~R 146 is a single bond bonded to *r, R 31 ~R 35 is a single bond bonded to *c, R 121 ~R 128 One selected from is a single bond bonded to *t.

[0311] In formula (2-4), m1, m7, and m21 each independently represent 0 or 1, and n21 represents 0 or 1. When m1 is 0, *p is a nitrogen atom N * binds to When m7 is 0, *c is a nitrogen atom N * binds to When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2is a single bond that bonds to

[0312] In formula (2-4), Y is an oxygen atom, a sulfur atom, or CR c R d and R c and R d are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. c and R d When both of R are aryl groups, R c and R d They may be linked together to form a spiro ring.

[0313] In formula (2-4), R 131 ~R 135 two adjacent R's selected from the above, which are not single bonds 141 ~R 146 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 31 ~R 35 Two adjacent ones selected from R 51 ~R 55 two adjacent ones selected from 121 ~R 124 and R 125 ~R 128 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A1 and the benzene ring B1, the benzene ring B1 and the benzene ring C1, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0314] [ka]

[0315] In formula (2-5), R 91 ~R 94 and R101 ~R 108 is as mentioned above.

[0316] In formula (2-5), R 151 ~R 155 , R 161 ~R 166 , R 81 ~R 85 , R 281 ~R 285 , R 61 ~R 68 and R 261 ~R 268 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. However, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 281 ~R 285 One of the following is selected: 2 is a single bond that connects to R 61 ~R 68 is a single bond bonded to *f, R 261 ~R 268 One of the following is selected:1 is a single bond that bonds to

[0317] In formula (2-5), m21 is 0 or 1, n21 is 0 or 1, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0318] In formula (2-5), m2 is 0 or 1, and when m2 is 0, *c 1 is a nitrogen atom N * and m12 is 0 or 1, and when m12 is 0, *c 2 is a nitrogen atom N * Combine with.

[0319] In formula (2-5), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 281 ~R 285 Two adjacent ones selected from R 61 ~R 68 and R 261 ~R 268 adjacent two selected from the above are each independently not bonded to each other, and therefore do not form a ring structure, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0320] [ka]

[0321] In formula (2-6), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0322] In formula (2-6), R 151 ~R 155 , R 161 ~R 166 , R 81 ~R 85 , R 281 ~R 285 , R 41 ~R 46 , R 61 ~R 68 and R 71 ~R 80 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. However, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 281 ~R 285 One of the following is selected: 2 is a single bond that connects to R 41 ~R 46is a single bond bonded to *d, and R 41 ~R 46 is a single bond bonded to *e, R 61 ~R 68 is a single bond bonded to *f, R 71 ~R 80 One selected from is a single bond bonded to *h.

[0323] In formula (2-6), m21 and m3 each independently represent 0 or 1, and n21 and n3 each independently represent 0 or 1. When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that connects to When m3 is 0 and n3 is 0, *e is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c 2 is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 281 ~R 285 One selected from is a single bond bonded to *e.

[0324] In formula (2-6), m2 is 0 or 1, and when m2 is 0, *c 1 is a nitrogen atom N * Combine with.

[0325] In formula (2-6), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds161 ~R 166 two adjacent R's selected from the above, which are not single bonds 281 ~R 285 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 Two adjacent ones selected from R 61 ~R 68 two adjacent ones selected from, and R 71 ~R 80 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A22 and the benzene ring B22, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0326] [ka]

[0327] In formula (2-7), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0328] In formula (2-7), R 151 ~R 155 , R 161 ~R 166 , R 81 ~R 85 , R 31 ~R 35 , R 61 ~R 68 and R 121 ~R 128 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 31 ~R 35 One of the following is selected: 2 is a single bond that connects to R 61 ~R 65 is a single bond bonded to *f, R 121 ~R 128 One selected from is a single bond bonded to *t.

[0329] In formula (2-7), m21 is 0 or 1, n21 is 0 or 1, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0330] In formula (2-7), m2 is 0 or 1, and when m2 is 0, *c 1 is a nitrogen atom N * and m7 is 0 or 1, and when m7 is 0, *c 2 is a nitrogen atom N * Combine with.

[0331] In formula (2-7), Y is an oxygen atom, a sulfur atom, or CR c R d and R c and R d are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. c and R d When both of R are aryl groups, R c and R d They may be linked together to form a spiro ring.

[0332] In formula (2-7), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 31 ~R 35 Two adjacent ones selected from R 61 ~R 68 and R 121 ~R 128 adjacent two selected from the above are each independently not bonded to each other, and therefore do not form a ring structure, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0333] [ka]

[0334] In formula (2-8), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0335] In formula (2-8), R 151 ~R 155 , R 161 ~R 166 , R 81 ~R85 , R 41 ~R 46 , R 281 ~R 285 , R 241 ~R 246 , R 71 ~R 80 and R 271 ~R 280 are each independently R in the above formula (1-1) 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 41 ~R 46 One selected from *d 1 is a single bond that connects to R 41 ~R 46 The other one selected from *e 1 is a single bond that connects to R 281 ~R 285 One of the following is selected: 2 is a single bond that connects to R 241 ~R 246 One selected from *d2 is a single bond that connects to R 241 ~R 246 The other one selected from *e 2 is a single bond that bonds to R 71 ~R 80 One selected from *h 1 is a single bond that connects to R 271 ~R 280 One selected from *h 2 is a single bond that bonds to

[0336] In formula (2-8), m3, m13, and m21 each independently represent 0 or 1, and n3, n13, and n21 each independently represent 0 or 1. When m3 is 0 and n3 is 0, *e 1 is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c 1 is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 81 ~R 85 One selected from *e 1 is a single bond that connects to When m13 is 0 and n13 is 0, *e 2 is a nitrogen atom N * binds to When m13 is 0 and n13 is 1, *c 2 is a nitrogen atom N * binds to When m13 is 1 and n13 is 0, R 281 ~R 285 One selected from *e 2 is a single bond that connects to When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155One of the following is selected: 2 is a single bond that bonds to

[0337] In formula (2-8), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 281 ~R 285 Two adjacent ones selected from R 241 ~R 246 Two adjacent ones selected from R 71 ~R 80 two adjacent ones selected from, and R 271 ~R 280 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A12 and the benzene ring B12, the benzene ring A22 and the benzene ring B22, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0338] [ka] In formula (2-9), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0339] In formula (2-9), R 151 ~R 155 , R 161 ~R 166 , R 81 ~R 85 , R 41 ~R 46 , R 31 ~R 35 , R 71 ~R 80 and R 121 ~R 128are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 151 ~R 155 One selected from *p 2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 81 ~R 85 One of the following is selected: 1 is a single bond that connects to R 41 ~R 46 is a single bond bonded to *d, and R 41 ~R 46 is a single bond bonded to *e, R 31 ~R 35 One of the following is selected: 2 is a single bond that connects to R 71 ~R 80 is a single bond bonded to *h, R 121 ~R 128 One selected from is a single bond bonded to *t.

[0340] In formula (2-9), m3 and m21 each independently represent 0 or 1, and n3 and n21 each independently represent 0 or 1. When m3 is 0 and n3 is 0, *e is a nitrogen atom N * binds to When m3 is 0 and n3 is 1, *c 1 is a nitrogen atom N * binds to When m3 is 1 and n3 is 0, R 81 ~R 85 is a single bond bonded to *e, When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0341] In formula (2-9), m7 is 0 or 1, and when m7 is 0, *c 2 is a nitrogen atom N * Combine with.

[0342] In formula (2-9), Y is an oxygen atom, a sulfur atom, or CR c R d and R c and R d are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. c and R d When both of R are aryl groups, R c and R d They may be linked together to form a spiro ring.

[0343] In formula (2-9), R 81 ~R 85 two adjacent R's selected from the above, which are not single bonds 41 ~R 46 two adjacent R's selected from the above, which are not single bonds 151 ~R155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 31 ~R 35 Two adjacent ones selected from R 71 ~R 80 two adjacent ones selected from, and R 121 ~R 128 adjacent two selected from the above are each independently not bonded to each other and therefore do not form a ring structure, and the benzene ring A12 and the benzene ring B12, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0344] [ka] In formula (2-10), R 91 ~R 94 and R 101 ~R 108 is as mentioned above.

[0345] In formula (2-10), R 151 ~R 155 , R 161 ~R 166 , R 31 ~R 35 , R 231 ~R 235 , R 121 ~R 128 and R 321 ~R 328 are each independently R in the above formula (1-1). 131 ~R 135 , R 141 ~R 146 , R 171 ~R 175 , R 181 ~R 186 , R 51 ~R 55 and R 191 ~R 195 The same applies to the preferred embodiments. however, R 151 ~R 155 One selected from *p2 is a single bond that connects to R 161 ~R 166 One selected from *q 2 is a single bond that connects to R 161 ~R 166 The other one selected from *r 2 is a single bond that connects to R 31 ~R 35 One of the following is selected: 1 is a single bond that connects to R 231 ~R 235 One of the following is selected: 2 is a single bond that connects to R 121 ~R 128 One selected from *t 1 is a single bond that connects to R 321 ~R 328 One selected from *t 2 is a single bond that bonds to

[0346] In formula (2-10), each m21 independently represents 0 or 1, and each n21 independently represents 0 or 1. When m21 is 0 and n21 is 0, *r 2 is a nitrogen atom N * binds to When m21 is 0 and n21 is 1, *p 2 is a nitrogen atom N * binds to When m21 is 1 and n21 is 0, R 151 ~R 155 One of the following is selected: 2 is a single bond that bonds to

[0347] In formula (2-10), m7 is 0 or 1, and when m7 is 0, *c 1 is a nitrogen atom N * and m17 is 0 or 1, and when m17 is 0, *c 2 is a nitrogen atom N * Combine with.

[0348] In formula (2-10), Y 1 and Y 2 are each independently an oxygen atom, a sulfur atom, or CR c R d and R c and R d are each independently a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. c and R d When both of R are aryl groups, R c and R d They may be linked together to form a spiro ring.

[0349] In formula (2-10), R 31 ~R 35 two adjacent R's selected from the above, which are not single bonds 151 ~R 155 two adjacent R's selected from the above, which are not single bonds 161 ~R 166 two adjacent R's selected from the above, which are not single bonds 231 ~R 235 Two adjacent ones selected from R 121 ~R 128 and R 321 ~R 328 adjacent two selected from the above are each independently not bonded to each other, and therefore do not form a ring structure, and the benzene ring A3 and the benzene ring B3 are not bridged.

[0350] Deuterium atom possessed by invention compound B Invention compound B contains at least one deuterium atom. Deuterium atoms may be intentionally introduced into Compound A of the invention by using deuterated compounds as some or all of the starting compounds. Here, examples of the partially or completely deuterated raw material compound include a compound that forms a 9-carbazolyl group in formula (2), a compound that forms a phenylene group in formula (2), a compound that forms a linker (L 4 , L5 , L 6 ), a compound forming the terminal (Ar 3 , Ar 4 ), and compounds that form

[0351] In equation (2), L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 91 ~R 94 and R 101 ~R 108 It is preferred that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in the following formula (2-11), the sum of a, b, c, d, e, f, and g is preferably 1 or more. [ka] In the formula (2-11), "Da" is R 101 ~R 108 indicates that a hydrogen atoms are deuterium atoms, and "Db" indicates that R 91 ~R 94 indicates that b hydrogen atoms are deuterium atoms, and "Dc" indicates that L 4 "Dd" indicates that c hydrogen atoms directly bonded to the arylene group or divalent heterocyclic group represented by Ar 4"De" indicates that d hydrogen atoms directly bonded to the aryl group or monovalent heterocyclic group represented by the formula (I) are deuterium atoms. 6 "Df" indicates that e hydrogen atoms directly bonded to the arylene group or divalent heterocyclic group represented by the formula are deuterium atoms, and "Df" indicates that L 5 "Dg" indicates that f hydrogen atoms directly bonded to the arylene group or divalent heterocyclic group represented by Ar 3 indicates that g of the hydrogen atoms directly bonded to the aryl group or monovalent heterocyclic group represented by the formula (I) are deuterium atoms.

[0352] Furthermore, in formula (2), at least one deuterium atom contained in the invention compound B is L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 91 ~R 94 and R 101 ~R 108 (i.e., in formula (2), Ar 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108 When is substituted, the substituent preferably does not contain a deuterium atom.

[0353] In equation (2), L 4a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 91 ~R 94 and R 101 ~R 108 It is preferred that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in formula (2-11), the sum of a, b, c, d, e, and f is preferably 1 or more.

[0354] Furthermore, in formula (2), at least one deuterium atom contained in the invention compound B is L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 91 ~R 94 and R 101 ~R 108 (i.e., in formula (2), Ar 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108When Ar is substituted, the substituent does not contain a deuterium atom, and Ar 3 A hydrogen atom directly bonded to the aryl group represented by Ar 3 It is more preferable that the hydrogen atom directly bonded to the monovalent heterocyclic group represented by does not include a deuterium atom.

[0355] In equation (2), L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 A hydrogen atom directly bonded to the monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by 91 ~R 94 It is more preferable that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in formula (2-11), the sum of b, c, d, e, f, and g is preferably 1 or more.

[0356] Furthermore, in formula (2), at least one deuterium atom contained in the invention compound B is L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by 91 ~R 94 (i.e., in formula (2), Ar 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108 When R is substituted, the substituent does not contain a deuterium atom, and 101 ~R 108 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0357] In equation (2), L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 A hydrogen atom directly bonded to a divalent heterocyclic group represented by 91 ~R 94 It is preferred that at least one of the hydrogen atoms represented by is a deuterium atom. That is, in formula (2-11), the sum of b, c, e, and f is preferably 1 or more.

[0358] Furthermore, in formula (2), at least one deuterium atom contained in the invention compound B is L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 A hydrogen atom directly bonded to a divalent heterocyclic group represented by 91 ~R 94(i.e., in formula (2), Ar 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108 When Ar is substituted, the substituent does not contain a deuterium atom, and Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by 101 ~R 108 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0359] In equation (2), L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by 4 At least one of the hydrogen atoms directly bonded to the monovalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (2-11), the sum of c, d, e, f, and g is preferably 1 or more.

[0360] Furthermore, in formula (2), at least one deuterium atom contained in invention compound B is L 4 a hydrogen atom directly bonded to the arylene group represented by 4a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by 4 and at least one hydrogen atom directly bonded to a monovalent heterocyclic group represented by 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108 When R is substituted, the substituent does not contain a deuterium atom, and 91 ~R 94 The hydrogen atom and R 101 ~R 108 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0361] In equation (2), L 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 At least one of the hydrogen atoms directly bonded to the divalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (2-11), the sum of c, e, and f is preferably 1 or more.

[0362] Furthermore, in formula (2), at least one deuterium atom contained in invention compound B is L 4a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 and at least one hydrogen atom directly bonded to a divalent heterocyclic group represented by 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108 When Ar is substituted, the substituent does not contain a deuterium atom, and Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 91 ~R 94 and R 101 ~R 108 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0363] In equation (2), L 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by 4 At least one of the hydrogen atoms directly bonded to the monovalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (2-11), the sum of d, e, f, and g is preferably 1 or more.

[0364] Furthermore, in formula (2), at least one deuterium atom contained in invention compound B is L 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by 4 and at least one hydrogen atom directly bonded to a monovalent heterocyclic group represented by 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108 When L is substituted, the substituent does not contain a deuterium atom, and 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to a divalent heterocyclic group represented by R 91 ~R 94 and R 101 ~R 108 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0365] In equation (2), L 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 At least one of the hydrogen atoms directly bonded to the divalent heterocyclic group represented by the formula (I) is preferably a deuterium atom. That is, in formula (2-11), the sum of e and f is preferably 1 or more.

[0366] Furthermore, in formula (2), at least one deuterium atom contained in invention compound B is L 5 a hydrogen atom directly bonded to the arylene group represented by 5 a hydrogen atom directly bonded to the divalent heterocyclic group represented by 6 a hydrogen atom directly bonded to the arylene group represented by 6 and at least one hydrogen atom directly bonded to a divalent heterocyclic group represented by 3 ,Ar 4 ,L 4 ~L 6 ,R 91 ~R 94 and R 101 ~R 108 When L is substituted, the substituent does not contain a deuterium atom, and 4 a hydrogen atom directly bonded to the arylene group represented by 4 a hydrogen atom directly bonded to a divalent heterocyclic group represented by Ar 3 A hydrogen atom directly bonded to an aryl group represented by Ar 3 a hydrogen atom directly bonded to a monovalent heterocyclic group represented by Ar 4 A hydrogen atom directly bonded to an aryl group represented by Ar 4 a hydrogen atom directly bonded to the monovalent heterocyclic group represented by R 91 ~R 94 and R 101 ~R 108 It is more preferable that the hydrogen atom represented by does not include a deuterium atom.

[0367] The deuteration rate of invention compound B depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain proportion of naturally occurring proton isotopes may be contained. Therefore, the deuteration rate of invention compound B shown below includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the proportion determined simply by counting the number of deuterium atoms represented by the chemical formula. The deuteration rate of the invention compound B is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and particularly preferably 50% or more.

[0368] Invention compound B may be a mixture containing a deuterated compound (a compound into which deuterium atoms have been intentionally introduced) and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture (the ratio of the number of deuterium atoms to the total number of hydrogen atoms in invention compound A contained in the mixture) is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and particularly preferably 50% or more and less than 100%.

[0369] The invention compound B is L 4 ~L 6 and R 91 ~R 94 The ratio of the number of deuterium atoms to the total number of hydrogen atoms is preferably 10% or more, more preferably 20% or more, even more preferably 30% or more, still more preferably 40% or more, and particularly preferably 50% or more.

[0370] Suitable examples of invention compound B include compounds represented by the following formulae (2-11-1) to (2-11-23).

[0371] [ka] (In formula (2-11-1), x+y+z+w+k+l+m+n=1 to 38, and each R is omitted.)

[0372] [ka] (In formula (2-11-2), x+y+z+w+k+l+m+n=1 to 38, and each R is omitted.)

[0373] [ka] (In formula (2-11-3), x+y+z+w+k+l+m+n=1 to 40, and each R is omitted.)

[0374] [ka] (In formula (2-11-4), x+y+z+w+k+l+m+n=1 to 40, and each R is omitted.)

[0375] [ka] (In equation (2-11-5), x+y+z+w+k+l+m=1 to 36, and each R is omitted.)

[0376] [ka] (In equation (2-11-6), x+y+z+w+k+l+m=1 to 36, and each R is omitted.)

[0377] [ka] (In equation (2-11-7), x+y+z+w+k+l+m=1 to 38, and each R is omitted.)

[0378] [ka] (In equation (2-11-8), x+y+z+w+k+l+m=1 to 36, and each R is omitted.)

[0379] [ka] (In equation (2-11-9), x+y+z+w+k+l+m=1 to 36, and each R is omitted.)

[0380] [ka] (In equation (2-11-10), x+y+z+w+k+l+m=1 to 36, and each R is omitted.)

[0381] [ka] (In equation (2-11-11), x+y+z+w+k+l+m=1 to 36, and each R is omitted.)

[0382] [ka] (In equation (2-11-12), x+y+z+k+l+m+n=1 to 34, and each R is omitted.)

[0383] [ka] (In equation (2-11-13), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0384] [ka] (In equation (2-11-14), x+y+z+k+l+m+n=1 to 38, and each R is omitted.)

[0385] [ka] (In equation (2-11-15), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0386] [ka] (In equation (2-11-16), x+y+z+k+l+m+n+o=1 to 38, and each R is omitted.)

[0387] [ka] (In equation (2-11-17), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0388] [ka] (In equation (2-11-18), x+y+z+k+l+m+n=1 to 38, and each R is omitted.)

[0389] [ka] (In equation (2-11-19), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0390] [ka] (In equation (2-11-20), x+y+z+k+l+m=1 to 42, and each R is omitted.)

[0391] [ka] (In equation (2-11-21), x+y+z+k+l+m=1 to 40, and each R is omitted.)

[0392] [ka] (In equation (2-11-22), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0393] [ka] (In equation (2-11-23), x+y+z+k+l+m+n=1 to 36, and each R is omitted.)

[0394] Unless otherwise specified, details of the substituents (optional substituents) in the case of "substituted or unsubstituted" included in the definition of each formula above are as described in the section "Substituents in the case of 'substituted or unsubstituted'".

[0395] Compound B of the invention can be easily produced by a person skilled in the art by referring to the synthesis examples below and known synthesis methods.

[0396] Specific examples of the invention compound are shown below, but are not limited to these exemplary compounds. The invention compound includes not only the compounds shown as the exemplary compounds below, but also compounds in which some hydrogen atoms are not deuterated due to synthesis techniques. In the following specific examples, D represents a deuterium atom.

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[0435] Materials for organic EL devices The material for organic EL devices, which is one embodiment of the present invention, contains the compound of the present invention. The content of the compound of the present invention in the material for organic EL devices is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The material for organic EL devices, which is one embodiment of the present invention, is useful for producing organic EL devices.

[0436] In one embodiment of the present invention, it is preferable that the invention compound further contains a protonated form of the invention compound, where all hydrogen atoms in the invention compound are protonated forms. The mixing molar ratio of the invention compound to the protonated form of the invention compound (invention compound:protonated form) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, even more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0437] In one embodiment of the present invention, it is preferable to contain at least two types of the invention compound.

[0438] In one aspect of the present invention, there is provided a material for an organic electroluminescence device, which comprises a first compound and a second compound, wherein the first compound is an invention compound, and the material for an organic electroluminescence device preferably contains the first compound in an amount of 1 mass % or more, and more preferably the first compound and the second compound are hole transport layer materials. The content of the first compound in the material for organic electroluminescence devices is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), even more preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%).

[0439] Organic EL element An organic EL device according to one embodiment of the present invention comprises an anode, a cathode, and organic layers disposed between the anode and the cathode. The organic layers include an emitting layer, and at least one of the organic layers contains a compound of the present invention. Examples of organic layers containing the compound of the invention include, but are not limited to, a hole transporting region (hole injection layer, hole transporting layer, electron blocking layer, exciton blocking layer, etc.) provided between an anode and an emitting layer, an emitting layer, a spacer layer, and an electron transporting region (electron injection layer, electron transporting layer, hole blocking layer, etc.) provided between a cathode and an emitting layer. The compound of the invention is preferably used as a material for the hole transporting region or the emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transporting region, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.

[0440] The organic EL device according to one embodiment of the present invention may be a fluorescent or phosphorescent monochromatic light-emitting device, a fluorescent / phosphorescent hybrid white light-emitting device, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, and is preferably a fluorescent light-emitting device. Here, the term "light-emitting unit" refers to a minimum unit that includes organic layers, at least one of which is a light-emitting layer, and emits light by recombination of injected holes and electrons.

[0441] For example, the following device configuration can be given as a typical device configuration of a simple type organic EL device. (1) Anode / light-emitting unit / cathode The light-emitting unit may also be a multi-layered structure having multiple phosphorescent or fluorescent light-emitting layers. In this case, a spacer layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer structure of a simple light-emitting unit is shown below. The layers in parentheses are optional. (a) (hole injection layer / ) hole transport layer / fluorescent light-emitting layer / electron transport layer ( / electron injection layer) (b) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer Electron transport layer ( / Electron injection layer) (c) (hole injection layer / ) hole transport layer / first fluorescent-emitting layer / second fluorescent-emitting layer / electron transport layer ( / electron injection layer) (d) (hole injection layer / ) hole transport layer / first phosphorescent-emitting layer / second phosphorescent-emitting layer / electron transport layer ( / electron injection layer) (e) (Hole injection layer / ) Hole transport layer / Phosphorescent emitting layer / Space layer / Fluorescent emitting layer / Electron transport layer ( / Electron injection layer) (f) (hole injection layer / ) hole transport layer / first phosphorescent-emitting layer / second phosphorescent-emitting layer / space layer / fluorescent-emitting layer / electron transport layer ( / electron injection layer) (g) (Hole injection layer / ) Hole transport layer / First phosphorescent-emitting layer / Space layer / Second phosphorescent-emitting layer / Space layer / Fluorescent-emitting layer / Electron transport layer ( / Electron injection layer) (h) (hole injection layer / ) hole transport layer / phosphorescent-emitting layer / space layer / first fluorescent-emitting layer / second fluorescent-emitting layer / electron transport layer ( / electron injection layer) (i) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (j) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Phosphorescent emitting layer / Electron transport layer ( / Electron injection layer) (k) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent light-emitting layer / Electron transport layer ( / Electron injection layer) (l) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Phosphorescent emitting layer / Electron transport layer ( / Electron injection layer) (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / electron transport layer ( / electron injection layer) (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent layer / Electron transport layer ( / Electron injection layer) (o) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light-emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent emitting layer / first electron transport layer / second electron transport layer ( / electron injection layer) (q) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Hole blocking layer / Electron transport layer ( / Electron injection layer) (r) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Hole blocking layer / Electron transport layer ( / Electron injection layer) (s) (Hole injection layer / ) Hole transport layer / Fluorescent light-emitting layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer) (t) (Hole injection layer / ) Hole transport layer / Phosphorescent emitting layer / Exciton blocking layer / Electron transport layer ( / Electron injection layer)

[0442] The phosphorescent or fluorescent emitting layers may each emit a different color of light. Specifically, the light emitting unit (f) may have a layer structure such as (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red emitting) / second phosphorescent emitting layer (green emitting) / spacer layer / fluorescent emitting layer (blue emitting) / electron transport layer. An electron blocking layer may be provided between each light-emitting layer and the hole transport layer or the spacer layer, as appropriate. A hole blocking layer may be provided between each light-emitting layer and the electron transport layer, as appropriate. By providing an electron blocking layer or a hole blocking layer, electrons or holes can be confined within the light-emitting layer, increasing the probability of charge recombination in the light-emitting layer and improving the luminous efficiency.

[0443] Typical device configurations of tandem organic EL devices include the following. (2) Anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode Here, the first light-emitting unit and the second light-emitting unit can be, for example, independently selected from the light-emitting units described above. The intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generating layer, electron withdrawing layer, connecting layer, or intermediate insulating layer, and can be made of known materials that supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0444] FIG. 1 is a schematic diagram showing an example of the configuration of an organic EL device according to one embodiment of the present invention. The organic EL device 1 includes a substrate 2, an anode 3, a cathode 4, and an emitting unit 10 disposed between the anode 3 and the cathode 4. The emitting unit 10 includes an emitting layer 5. A hole-transporting region 6 (e.g., a hole-injection layer, a hole-transporting layer) is disposed between the emitting layer 5 and the anode 3, and an electron-transporting region 7 (e.g., an electron-injection layer, an electron-transporting layer) is disposed between the emitting layer 5 and the cathode 4. An electron-blocking layer (not shown) may be disposed on the anode 3 side of the emitting layer 5, and a hole-blocking layer (not shown) may be disposed on the cathode 4 side of the emitting layer 5. This allows electrons and holes to be trapped in the emitting layer 5, further increasing the efficiency of exciton generation in the emitting layer 5.

[0445] 2 is a schematic diagram showing another configuration of an organic EL device according to one embodiment of the present invention. The organic EL device 11 includes a substrate 2, an anode 3, a cathode 4, and an emitting unit 20 disposed between the anode 3 and the cathode 4. The emitting unit 20 includes an emitting layer 5. The hole transporting region disposed between the anode 3 and the emitting layer 5 is formed of a hole injection layer 6a, a first hole transporting layer 6b, and a second hole transporting layer 6c. The electron transporting region disposed between the emitting layer 5 and the cathode 4 is formed of a first electron transporting layer 7a and a second electron transporting layer 7b.

[0446] In the present invention, a host combined with a fluorescent dopant (fluorescent-emitting material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant is referred to as a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished solely by molecular structure. That is, a phosphorescent host refers to a material that forms a phosphorescent-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent-emitting layer. The same applies to fluorescent hosts.

[0447] substrate The substrate is used as a support for the organic EL device. For example, a glass, quartz, or plastic plate can be used as the substrate. A flexible substrate can also be used. Examples of flexible substrates include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride. An inorganic vapor-deposited film can also be used.

[0448] 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, indium oxide containing tungsten oxide and 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 these metals (e.g., titanium nitride).

[0449] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing indium oxide and 1 to 10 wt% zinc oxide, while indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing indium oxide and 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or other methods.

[0450] The hole injection layer formed in contact with the anode is formed using a material that easily injects holes regardless of the work function of the anode, and therefore materials that are commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and 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.

[0451] hole injection layer The hole injection layer is a layer containing a material with high hole injection properties (hole injection material), and is formed between the anode and the light emitting layer, or, if present, between the hole transport layer and the anode.

[0452] Examples of hole injection materials that can be used other than the compound of the present invention include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0453] The small organic compounds 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD), Examples of the hole injection layer material include aromatic amine compounds such as 3-[N-(9-phenylcarbazol-3-yl)-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).

[0454] Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. Examples include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). Acid-added polymer compounds, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0455] Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K). [ka]

[0456] (In the above formula, R 201 ~R 206 are each independently a cyano group, -CONH2, a carboxyl group, or -COOR 207 (R 207 represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms. 201 and R 202 , R 203 and R 204 , and R 205 and R 206 adjacent two selected from may be bonded to each other to form a group represented by -CO-O-CO-.) R 207 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

[0457] hole transport layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is formed between the anode and the light emitting layer, or, if present, between the hole injection layer and the light emitting layer. The compound of the invention may be used alone or in combination with the following compound in the hole transport layer.

[0458] The hole transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). In one embodiment of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, an electron blocking layer, as described below, may be interposed between the hole transport layer and the light-emitting layer of the single-layer structure, or between the hole transport layer closest to the light-emitting layer in the multilayer structure and the light-emitting layer. In the hole transport layer of the two-layer structure, the compound of the invention may be contained in either the first hole transport layer or the second hole transport layer, or may be contained in both. In one embodiment of the present invention, the compound of the present invention is preferably contained only in the first hole transport layer, in another embodiment, the compound of the present invention is preferably contained only in the second hole transport layer, and in yet another embodiment, the compound of the present invention is preferably contained in both the first hole transport layer and the second hole transport layer.

[0459] As the hole transport layer material other than the compound of the present invention, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl) )-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). -6 cm 2 / Vs or higher.

[0460] Examples of carbazole derivatives include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA). Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth). Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, compounds other than those mentioned above may be used as long as they have a higher hole transporting property than an electron transporting property.

[0461] Dopant materials for the light-emitting layer The light-emitting layer is a layer containing a highly light-emitting material (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state.

[0462] Examples of blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc.

[0463] Green fluorescent materials that can be used in the light-emitting layer include aromatic amine derivatives, etc. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[ 9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.

[0464] Red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives, diamine derivatives, etc. Specific examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[0465] Examples of blue phosphorescent materials that can be used in the light-emitting layer include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Specific examples include bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated as FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviated as FIracac).

[0466] Green phosphorescent materials that can be used in the light-emitting layer include iridium complexes, such as tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

[0467] As the red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used. Specific examples include organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (abbreviation: PtOEP).

[0468] Furthermore, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electron transitions between different multiplicities).

[0469] Host material for the emitting layer The light-emitting layer may be configured by dispersing the above-mentioned dopant material in another material (host material). It is preferable to use a material that has a higher lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the dopant material.

[0470] Examples of the host material include (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, (3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; (4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives are used.

[0471] For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ); Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), and bathocuproine (abbreviation: BCP); 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-Bu condensed aromatic compounds such as DNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripylene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), and 6,12-dimethoxy-5,11-diphenylchrysene; and N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated as CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviated as DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviated as PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviated as PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H Aromatic amine compounds such as 2PCAPA-carbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB or α-NPD), TPD-bis[N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), and BSPB-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (BSPB) can be used. Multiple host materials can be used.

[0472] In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as the host material.

[0473] [ka]

[0474] [ka]

[0475] [ka]

[0476] electron transport layer The electron transport layer is a layer containing a material with high electron transporting properties (electron transport material), and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer. The electron transport layer may have a single-layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the electron transport layer closest to the anode in the multilayer structure, for example, the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole-blocking layer, as described below, may be interposed between the electron transport layer and the light-emitting layer of the single-layer structure, or between the electron transport layer closest to the light-emitting layer and the light-emitting layer in the multilayer structure.

[0477] The electron transport layer may contain, for example, (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; (3) Polymer compounds can be used.

[0478] Examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

[0479] Examples of heteroaromatic compounds include 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: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

[0480] Examples of polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0481] The above materials are 10 -6 cm 2 It is a material having an electron mobility of 1 / Vs or more. Note that materials other than those mentioned above may be used for the electron transport layer as long as they have a higher electron transport property than a hole transport property.

[0482] electron injection layer The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. A mixture of these compounds can also be used. Alternatively, an electron-transporting material containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), may be used. In this case, electrons can be injected from the cathode more efficiently. Alternatively, the electron injection layer may be formed using a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the accepted electrons. Specifically, for example, the materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) described above can be used. The electron donor may be any material that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as 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.

[0483] 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.

[0484] Insulation layer In organic EL devices, pixel defects due to leakage and short circuits are likely to occur because an electric field is applied to an ultra-thin film. To prevent this, an insulating layer made of an insulating thin film may be inserted between a pair of electrodes. Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Mixtures or laminates of these may also be used.

[0485] Space Layer The spacer layer is a layer provided between a fluorescent-emitting layer and a phosphorescent-emitting layer, for example, when the fluorescent-emitting layer and the phosphorescent-emitting layer are laminated, in order to prevent excitons generated in the phosphorescent-emitting layer from diffusing into the fluorescent-emitting layer or to adjust the carrier balance. The spacer layer can also be provided between multiple phosphorescent-emitting layers. Since the spacer layer is provided between the light-emitting layers, it is preferably made of a material that has both electron transport and hole transport properties. Furthermore, to prevent triplet energy diffusion in the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy be 2.6 eV or more. Materials used for the spacer layer include the same materials as those used for the hole transport layer described above.

[0486] blocking layer A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and confining the excitons within the light-emitting layer.

[0487] Each layer of the organic EL device can be formed by a conventionally known vapor deposition method, coating method, etc. For example, the layers can be formed by a conventionally known vapor deposition method such as vacuum vapor deposition or molecular beam deposition (MBE), or by a coating method using a solution of a compound that forms the layer, such as dipping, spin coating, casting, bar coating, or roll coating.

[0488] There are no particular restrictions on the thickness of each layer, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, and conversely, if the thickness is too thick, a high driving voltage is required, resulting in poor efficiency. Therefore, the thickness is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0489] Examples of embodiments of the organic EL device of the present invention include a first embodiment in which the second hole transport layer contains a compound of the present invention and the first hole transport layer does not contain a compound of the present invention; a second embodiment in which both the first hole transport layer and the second hole transport layer contain a compound of the present invention; and a third embodiment in which the first hole transport layer contains a compound of the present invention and the second hole transport layer does not contain a compound of the present invention.

[0490] electronic equipment The organic EL element can be suitably used in display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, etc., and electronic devices such as light-emitting devices for lighting and vehicle lamps. [Example]

[0491] Examples of the present invention will be described below, but the present invention is not limited to these examples.

[0492] The structures of compounds Inv1 and Inv7, which are compounds of the invention A represented by formula (1) and used in the production of the organic EL devices of Examples 1 and 2, are shown below. [ka]

[0493] [ka]

[0494] The structure of the comparative compound Ref1 used in the production of the organic EL device of Comparative Example 1 is shown below. [ka]

[0495] The structures of other compounds used in the production of the organic EL devices of Examples 1 and 2 and Comparative Example 1 are shown below. [ka] [ka] [ka]

[0496] Fabrication of organic EL devices An organic EL device was fabricated and evaluated as follows.

[0497] Example 1 A 25mm x 75mm x 1.1mm 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 30 minutes. The ITO film thickness was 130nm. The glass substrate with the cleaned transparent electrode was mounted on a substrate holder of a vacuum deposition apparatus, and the compound HTA and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of the compound HTA to the compound HA (HTA:HA) was 97:3. Next, the compound HTA was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compound Inv1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm. Next, a compound BH (host material) and a compound BD (dopant material) were co-deposited on the second hole transport layer to form a 25 nm thick light-emitting layer. The mass ratio of the compound BH to the compound BD (BH:BD) was 96:4. Next, the compound ETA was vapor-deposited on the light-emitting layer to form a first electron transport layer having a thickness of 5 nm. Next, a second electron transport layer having a thickness of 20 nm was formed on the first electron transport layer by co-depositing the compounds ETB and Liq at a mass ratio of 50:50 (ETB:Liq). Next, LiF was vapor deposited on this second electron transport layer to form an electron injection electrode having a thickness of 1 nm. Then, metal Al was vapor-deposited on this electron injecting electrode to form a metal cathode with a film thickness of 50 nm. The layer structure of the organic EL device of Example 1 thus obtained is shown below. ITO(130) / HTA:HA=97:3(10) / HTA(80) / Compound Inv1(10) / BH:BD=96:4(25) / ETA(5) / ETB:Liq=50:50(20) / LiF(1) / Al(50) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0498] Measurement of device life (LT97) The resulting organic EL device was subjected to a current density of 50 mA / cm 2 The time (h) until the brightness decreased to 97% of the initial brightness was measured, and this was taken as the 97% lifespan (LT97). The results are shown in Table 1.

[0499] Example 2 Each organic EL device was fabricated in the same manner as in Example 1, except that the material for the second hole transport layer was changed to compound Inv7 as shown in Table 1 below, and LT97 was measured. The results are shown in Table 1.

[0500] Comparative Example 1 Each organic EL device was produced in the same manner as in Example 1, except that the material for the second hole transport layer was changed to comparative compound Ref1 as shown in Table 1 below, and LT97 was measured. The results are shown in Table 1.

[0501] [Table 1]

[0502] As is clear from the results in Table 1, the monoamines satisfying the requirements of the present invention (compounds Inv1 and Inv7) provide organic EL devices with significantly improved device life compared to the monoamine not satisfying the requirements of the present invention (comparative compound Ref1).

[0503] The structures of compounds Inv1, Inv3, Inv7, Inv9, Inv10, Inv11, and Inv13, which are compounds of the invention A represented by formula (1) and used in the production of the organic EL devices of Examples 3 to 11, as well as the structures of compounds Inv4 and Inv12, are shown below. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0504] The structures of comparative compounds Ref1 and Ref2 used in the production of the organic EL devices of Comparative Examples 2 and 3 are shown below. [ka] [ka]

[0505] The structures of other compounds used in the production of the organic EL devices of Examples 3 to 11 and Comparative Examples 2 and 3 are shown below. [ka] [ka]

[0506] Fabrication of organic EL devices An organic EL device was fabricated and evaluated as follows.

[0507] Example 3 A 25mm x 75mm x 1.1mm 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 30 minutes. The ITO film thickness was 130nm. The glass substrate with the cleaned transparent electrode was mounted on a substrate holder of a vacuum deposition apparatus, and Compound HT-1 and Compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The mass ratio of Compound HT-1 to Compound HA (HT-1:HA) was 97:3. Next, the compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, the compound Inv1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm. Next, a 25 nm-thick light-emitting layer was formed on the second hole transport layer by co-depositing Compound BH-1 (host material) and Compound BD (dopant material). The mass ratio of Compound BH-1 to Compound BD (BH-1:BD) was 96:4. Next, the compound ET-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 10 nm. Next, the compound ET-2 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm. Next, LiF was vapor deposited on this second electron transport layer to form an electron injection electrode having a thickness of 1 nm. Then, metal Al was vapor-deposited on this electron injecting electrode to form a metal cathode with a film thickness of 50 nm. The layer structure of the organic EL device of Example 1 thus obtained is shown below. ITO(130) / HT-1:HA=97:3(10) / HT-1(80) / Compound Inv1(10) / BH-1:BD=96:4(25) / ET-1(10) / ET-2(15) / LiF(1) / Al(50) In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

[0508] Measurement of device life (LT95) The resulting organic EL device was subjected to a current density of 50 mA / cm 2 The time (h) until the brightness decreased to 95% of the initial brightness was measured, and this was taken as the 95% lifespan (LT95). The results are shown in Table 1.

[0509] Examples 4 to 11 Organic EL devices were fabricated and their LT95 was measured in the same manner as in Example 3, except that the second hole transport layer material was changed to Compound Inv3, Compound Inv4, Compound Inv7, Compound Inv9, Compound Inv10, Compound Inv11, Compound Inv12, or Compound Inv13, respectively, as shown in Table 1. The results are shown in Table 2.

[0510] Comparative Examples 2 and 3 Organic EL devices were fabricated and measured for LT95 in the same manner as in Example 1, except that the second hole transport layer material was changed to comparative compound Ref1 or comparative compound Ref2, as shown in Table 2. The results are shown in Table 2.

[0511] [Table 2]

[0512] As is clear from the results in Table 2, the monoamines satisfying the requirements of the present invention (compound Inv1, compound Inv3, compound Inv4, compound Inv7, compound Inv9, compound Inv10, compound Inv11, compound Inv12, and compound Inv13) provide organic EL devices with significantly improved device life, compared to the monoamines not satisfying the requirements of the present invention (comparative compound Ref1 and comparative compound Ref2).

[0513] Compound synthesis Compounds Inv1 to 15 synthesized in Synthesis Examples 1 to 8 are shown below. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0514] Intermediate synthesis example 1: Synthesis of intermediate A [ka]

[0515] Under an argon atmosphere, aniline-2,3,4,5,6-d5 (2.19 g, 22.33 mmol), bromobenzene-d5 (3.29 g, 20.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (372 mg, 0.41 mmol), BINAP (506 mg, 0.812 mmol), sodium t-butoxide (2.15 g, 22.33 mmol), and toluene (200 ml) were added and heated and stirred at 100 °C for 3 hours. After cooling, the mixture was filtered and the resulting residue was purified by column chromatography to obtain intermediate A (3.59 g). The yield was 99%.

[0516] Intermediate synthesis example 2: Synthesis of intermediate C [ka] Under an argon atmosphere, intermediate A (2.9 g, 16.18 mmol) and DMF (55 ml) were mixed, and N-bromosuccinimide (5.76 g, 32.4 mmol) was added at 0°C. Water and ethyl acetate were added for extraction, and the resulting organic layer was evaporated under reduced pressure to obtain intermediate B. Intermediate B was subjected to the next reaction without purification. Under an argon atmosphere, intermediate B (6.41 g, 19.12 mmol), phenylboronic acid (5.83 g, 47.8 mmol), bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (406 mg, 0.574 mmol), and 1,4-dioxane (100 mL) were mixed, and an aqueous potassium phosphate solution was added. After heating and stirring at 110°C for 5 hours and allowing to cool, the mixture was filtered and purified by column chromatography and recrystallization to obtain intermediate C (3.9 g). The yield was 62% (two steps).

[0517] Synthesis Example 1: Synthesis of Compound Inv1 [ka]

[0518] Under an argon atmosphere, intermediate C (2.9 g, 8.8 mmol), intermediate D (2.83 g, 8.0 mmol), which was synthesized by a literature method, tris(dibenzylideneacetone)dipalladium(0) (147 mg, 0.16 mmol), sodium t-butoxide (1.07 g, 11.2 mmol), and xylene (50 mL) were added and heated and stirred at 140 °C for 1 hour. After cooling, the mixture was filtered and purified by column chromatography to synthesize compound Inv1 (3.6 g). The yield was 70%. Mass spectrometry analysis of the resulting product revealed that it was compound Inv1, with a molecular weight of 646.86 and an m / e of 646.

[0519] Synthesis Example 2: Synthesis of Compound Inv2 [ka]

[0520] Intermediate E was obtained by a similar method to that used in the synthesis of intermediate C, except that 1-naphthaleneboronic acid was used instead of phenylboronic acid. Furthermore, compound Inv2 was synthesized by a similar method to that used in the synthesis of compound Inv1, except that intermediate E was used instead of intermediate C. Mass spectrum analysis revealed that it was compound Inv2, with a molecular weight of 746.98 and an m / e of 746.

[0521] Synthesis Example 3: Synthesis of Compound Inv3 [ka]

[0522] Intermediate F was obtained by a similar method to that used in the synthesis of intermediate C, except that phenylboronic acid-d5 was used instead of phenylboronic acid. Furthermore, compound Inv3 was synthesized by a similar method to that used in the synthesis of compound Inv1, except that intermediate F was used instead of intermediate C. Mass spectrum analysis revealed that it was compound Inv3, with a molecular weight of 656.92 and an m / e of 656.

[0523] Synthesis Example 4: Synthesis of Compound Inv4 [ka]

[0524] In the synthesis of compound Inv1, compound Inv4 was synthesized in the same manner, except that intermediate G, which had been synthesized by a method known in the literature, was used instead of intermediate D. Mass spectrum analysis revealed that it was compound Inv4, with a molecular weight of 646.86 and an m / e of 646.

[0525] Synthesis Example 5: Synthesis of Compound Inv5 [ka]

[0526] Compound Inv5 was synthesized in the same manner as in the synthesis of compound Inv2, except that intermediate G was used instead of intermediate D. Mass spectrum analysis revealed that it was compound Inv5, with a molecular weight of 746.98 and m / e = 746.

[0527] Synthesis Example 6: Synthesis of Compound Inv6 [ka]

[0528] Compound Inv6 was synthesized in the same manner as in the synthesis of compound Inv3, except that intermediate G was used instead of intermediate D. Mass spectrum analysis revealed that it was compound Inv6, with a molecular weight of 656.92 and m / e = 656.

[0529] Intermediate Synthesis Example 3: Synthesis of Intermediate I [ka] Under an argon atmosphere, 1,4-dibromobenzene-2,3,5,6-d4 (2.5 g, 10.42 mmol) and THF (105 ml) were mixed, and n-butyllithium (1.59 M, 6.55 ml) was added dropwise at -78 ° C. Then, a mixture of iodine (3.97 g, 15.63 mmol) and THF (25 ml) was added dropwise at -78 ° C. and stirred for 30 minutes. After that, water and aqueous sodium thiosulfate solution were added, the mixture was warmed to room temperature, extracted with dichloromethane, and the resulting organic layer was distilled under reduced pressure to obtain 1-bromo-4-iodobenzene-2,3,5,6-d4. Under an argon atmosphere, intermediate C (4.12 g, 12.5 mmol), 1-bromo-4-iodobenzene-2,3,5,6-d4 (4.3 g, 15.0 mmol), palladium(II) acetate (56 mg, 0.25 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (145 mg, 0.25 mmol), sodium t-butoxide (1.68 g, 17.5 mmol), and toluene (120 ml) were mixed and heated with stirring at 100°C for 3 hours. After cooling, the mixture was filtered and the resulting residue was washed with methanol to obtain intermediate I. The yield was 98% (two steps).

[0530] Intermediate Synthesis Example 4: Synthesis of Intermediate J [ka]

[0531] Under an argon atmosphere, intermediate I (4.5 g, 9.21 mmol), bis(pinacolato)diboron (2.81 g, 11.05 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (226 mg, 0.28 mmol), potassium acetate (2.71 g, 27.6 mmol), and 1,4-dioxane (47 ml) were mixed and heated with stirring at 110°C for 4 hours. After cooling, water and ethyl acetate were added for extraction. The resulting organic layer was evaporated under reduced pressure to obtain intermediate J.

[0532] Synthesis Example 7: Synthesis of Compound Inv7 [ka]

[0533] Intermediate J (4.93 g, 9.21 mmol), 9-(3-bromophenyl)carbazole (4.45 g, 13.82 mmol), tris(dibenzylideneacetone)dipalladium(0) (169 mg, 0.18 mmol), [4-(N,N-dimethylamino)phenyl]di-t-butylphosphine (196 mg, 0.74 mmol), potassium phosphate (5.87 g, 27.6 mmol), 1,4-dioxane (75 mL), and water (15 mL) were mixed under an argon atmosphere and heated with stirring at 110 °C for 4 hours. After cooling, the mixture was extracted with toluene and the resulting organic layer was evaporated under reduced pressure. The residue was purified by column chromatography and recrystallization to synthesize compound Inv7. The yield was 40% (two steps). Mass spectrometry analysis revealed that the product was compound Inv7, with a molecular weight of 650.89 and an m / e of 650.

[0534] Synthesis Example 8: Synthesis of Compound Inv8 [ka] Compound Inv8 was synthesized in the same manner as compound Inv7, except that 9-(2-bromophenyl)carbazole was used instead of 9-(3-bromophenyl)carbazole. Mass spectrometry analysis revealed that it was compound Inv8, with a molecular weight of 650.89 and an m / e of 650.

[0535] Synthesis Example 9: Synthesis of Compound Inv9 [ka] Compound Inv9 was synthesized in the same manner as in the synthesis of compound Inv1, except that intermediate K was used instead of intermediate C and intermediate L was used instead of intermediate D. Mass spectrometry analysis revealed that it was compound Inv9, with a molecular weight of 642.84 and m / e = 642.

[0536] Intermediate Synthesis Example 5: Synthesis of Intermediate O [ka] Under an argon atmosphere, a mixture of 1,4-dibromobenzene-2,3,5,6-d4 (2.5 g, 10.4 mmol), (3-(9H-carbazol-9-yl)phenyl)boronic acid 3.59 g (12.5 mmol), tetrakis(triphenylphosphine)palladium(0) 0.358 g (0.31 mmol), 2 M aqueous sodium carbonate 10.4 mL (20.8 mmol), and DME 50 mL was heated and stirred at 70 °C for 24 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3.18 g of a white solid. The yield was 76%.

[0537] Synthesis Example 10: Synthesis of Compound Inv10 [ka] Compound Inv10 was synthesized in the same manner as in the synthesis of compound Inv1, except that N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine was used instead of intermediate C and intermediate O was used instead of intermediate D. Mass spectrum analysis showed that it was compound Inv10, with a molecular weight of 642.84 and m / e = 642.

[0538] Intermediate Synthesis Example 6: Synthesis of Intermediate Q [ka] Intermediate Q was obtained in the same manner as in the synthesis of intermediate O, except that 4-biphenylboronic acid was used instead of (3-(9H-carbazol-9-yl)phenyl)boronic acid.

[0539] Synthesis Example 11: Synthesis of Compound Inv11 [ka] Compound Inv11 was synthesized in the same manner as compound 1, except that intermediate K was used instead of intermediate C and intermediate Q was used instead of intermediate D. Mass spectrum analysis showed that it was compound Inv11, with a molecular weight of 718.94 and m / e = 718.

[0540] Synthesis Example 12: Synthesis of Compound Inv12 [ka] Compound Inv12 was synthesized in the same manner as compound 1, except that intermediate M was used instead of intermediate C and intermediate Q was used instead of intermediate D. Mass spectrum analysis showed that it was compound Inv12, with a molecular weight of 718.94 and m / e = 718.

[0541] Synthesis Example 13: Synthesis of Compound Inv13 [ka] Compound Inv13 was synthesized in the same manner as compound 1, except that intermediate R was used instead of intermediate C and intermediate L was used instead of intermediate D. Mass spectrum analysis showed that the compound was compound Inv13, with a molecular weight of 732.92 and m / e = 732.

[0542] Synthesis Example 14: Synthesis of Compound Inv14 [ka] Compound Inv-14 was synthesized in the same manner as in the synthesis of Compound 1, except that intermediate M was used instead of intermediate C and intermediate L was used instead of intermediate D. Mass spectrometry analysis revealed that the compound was Inv-14, with a molecular weight of 642.84 and an m / e of 642.

[0543] Intermediate Synthesis Example 7: Synthesis of Intermediate P [ka] Intermediate P was obtained in the same manner as in the synthesis of intermediate O, except that (2-(9H-carbazol-9-yl)phenyl)boronic acid was used instead of (3-(9H-carbazol-9-yl)phenyl)boronic acid in the synthesis of intermediate O.

[0544] Synthesis Example 15: Synthesis of Compound Inv15 [ka] Compound Inv15 was synthesized in the same manner as in the synthesis of compound 1, except that N-[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4-amine was used instead of intermediate C and intermediate P was used instead of intermediate D. Mass spectrum analysis showed that it was compound Inv15, with a molecular weight of 642.84 and m / e = 642. [Explanation of symbols]

[0545] 1, 11 Organic EL element 2 boards 3 Anode 4 cathode 5. Light-emitting layer 6. Hole transport zone (hole transport layer) 6a Hole injection layer 6b First hole transport layer 6c Second hole transport layer 7 Electron transport zone (electron transport layer) 7a First electron transport layer 7b Second electron transport layer 10, 20 light-emitting units

Claims

1. A compound having at least one deuterium atom and represented by the following formula (1-11-1), (1-11-5), (1-11-11), or (1-11-13): 【Chemistry 1】 (In formula (1-11-1), x + y + z + k + l + m + n = 1 to 34, provided that any one of l, m, n, and z is 1 or greater.) 【Chemistry 2】 (In formula (1-11-5), x+y+z+k+l+m+n+o=1 to 38, provided that m is 1 or more.) 【Transformation 3】 (In formula (1-11-11), x + y + z + k + l + m + n = 1 to 38, provided that l and m are 1 or greater.) 【Chemistry 4】 (In formula (1-11-13), x + y + z + k + l + m + n = 1 to 36, provided that any one of l, m, n, and z is 1 or greater.)

2. The compound according to claim 1, wherein the deuteration rate of the compound represented by formula (1-11-1), formula (1-11-5), formula (1-11-11), or formula (1-11-13) is 10% or more.

3. The compound according to claim 2, wherein the deuteration rate of the compound represented by formula (1-11-1), formula (1-11-5), formula (1-11-11), or formula (1-11-13) is 50% or more.

4. A compound having at least one deuterium atom and represented by the following formula (2-11-12), (2-11-14), or (2-11-16): 【Transformation 5】 (In formula (2-11-12), x + y + z + k + l + m + n = 1 to 34, provided that l and m are 1 or greater.) 【Transformation 6】 (In formula (2-11-14), x + y + z + k + l + m + n = 1 to 38, provided that l and m are 1 or greater.) 【Transformation 7】 (In formula (2-11-16), x + y + z + k + l + m + n + o = 1 to 38, provided that m is 1 or more.)

5. The compound described in claim 4, wherein the deuteration rate of the compound represented by formula (2-11-12), formula (2-11-14), or formula (2-11-16) is 10% or more.

6. The compound described in claim 5, wherein the deuteration rate of the compound represented by formula (2-11-12), formula (2-11-14), or formula (2-11-16) is 50% or more.

7. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 6.

8. 8. The material for an organic electroluminescence device according to claim 7, further comprising a protonated form of the compound according to any one of claims 1 to 6, wherein all hydrogen atoms in the protonated form are proton atoms.

9. The material for an organic electroluminescence device according to claim 7, comprising at least two compounds according to any one of claims 1 to 6.

10. A material for an organic electroluminescence device, comprising a first compound and a second compound, The first compound is a compound according to any one of claims 1 to 6, The material for an organic electroluminescence device according to claim 7 , wherein the material for an organic electroluminescence device contains the first compound in an amount of 1 mass % or more.

11. The material for an organic electroluminescence device according to claim 10 , wherein the first compound and the second compound are hole transport layer materials.

12. An organic electroluminescence device having a cathode, an anode, and an organic layer between the cathode and the anode, wherein the organic layer includes an emitting layer, and at least one layer of the organic layer includes the compound according to any one of claims 1 to 6.

13. 13. The organic electroluminescence device according to claim 12, wherein the organic layer comprises a hole transporting region between the anode and the light emitting layer, and the hole transporting region comprises the compound according to any one of claims 1 to 6.

14. the hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side; 14. The organic electroluminescence device according to claim 13, wherein at least one of the first hole transport layer and the second hole transport layer contains the compound according to any one of claims 1 to 6.

15. 15. The organic electroluminescence device according to claim 12, wherein the light-emitting layer contains a fluorescent dopant material.

16. 15. The organic electroluminescence device according to claim 12, wherein the light-emitting layer contains a phosphorescent dopant material.

17. An electronic device comprising the organic electroluminescence element according to any one of claims 12 to 16.

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