Compound and organic electroluminescent device

Abstract

Compounds represented by formulae (1-1) and (1-3) or compounds represented by formulae (1-2) and (1-3). In the formulae, at least one of R1 to R16 is, for example, an (un)substituted alkyl group having 1-50 carbon atoms. In the compounds represented by formulae (1-1) and (1-3), at least one of R5 to R7 and R14 to R16 is -N(R36)(R37). In the compounds represented by formulae (1-2) and (1-3), at least one of R2 to R16 is -N(R36)(R37).

Description

[Technical field]

[0001] The present invention relates to a novel compound and an organic electroluminescence device. [Background technology]

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an organic EL element), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] Conventional organic EL elements still do not have sufficient element performance. Although the materials used in organic EL elements have been gradually improved to enhance element performance, further improvements in performance are required. In particular, improving the lifespan of organic EL elements is an important issue that will lead to the lifespan of practical products, so materials that can realize long-life organic EL elements are required.

[0004] Patent Document 1 discloses the use of a compound having a specific structure in the light-emitting layer of an organic EL device. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2019 / 111971 Summary of the Invention

[0006] An object of the present invention is to provide a compound which can be used to produce an organic EL device having a long life.

[0007] Means for Solving the Problems The present inventors have conducted extensive research to achieve the above object, and as a result have discovered that use of a compound having a specific structure makes it possible to obtain an organic EL device having an excellent lifetime, thereby completing the present invention. According to the present invention, the following compounds and the like are provided: A compound represented by the following formulas (1-1) and (1-3), or a compound represented by the following formulas (1-2) and (1-3). [ka] (In the formula (1-1), the formula (1-2) and the formula (1-3), Ring A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. The two bonds * in the formula (1-1) are each bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring of the ring A or a ring-forming atom of the heterocycle. The three bonds * in the formula (1-2) are bonded to ring-forming carbon atoms of the aromatic hydrocarbon ring of the ring A or to ring-forming atoms of the heterocycle. R1~R 16 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The R to R do not form a substituted or unsubstituted saturated or unsaturated ring. 16 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. In the compounds represented by the formula (1-1) and the formula (1-3), R5 to R7 and R 14 ~R 16 At least one of -N(R 36 )(R 37 In the compounds represented by the formulas (1-2) and (1-3), R to R 16 At least one of -N(R 36 )(R 37 ). R1~R 16 At least one pair of adjacent two or more of R to R 16 at least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 31 ~R 37 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 31 ~R 37 If there are multiple of each of them, there are multiple R31 ~R 37 may be the same or different.)

[0008] According to the present invention, a compound capable of producing an organic EL device having a long life can be provided. [Brief description of the drawings]

[0009] [Figure 1] FIG. 1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] [Definition] In this specification, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

[0011] In the present 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 indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0012] In this specification, the number of ring carbon atoms represents 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 (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is 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, the number of ring carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms of a 9,9'-spirobifluorenyl group is 25. In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number 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. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number 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.

[0013] 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 compound, a fused ring compound, and a ring assembly). The number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent. 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 a pyridine ring is 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. For example, hydrogen atoms bonded to carbon atoms of a quinazoline ring or atoms constituting a substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0014] In the present specification, the "number of carbon atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents 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.

[0015] In the present specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having the number of atoms XX to YY" represents 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.

[0016] In this specification, the term "unsubstituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and the term "substituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In the present specification, "unsubstituted" in the case 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 protium atom, a deuterium atom, or a tritium atom. In the present specification, "substituted" in the case 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 case 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.

[0017] "Substituents Described Herein" The substituents described in this specification will be described below.

[0018] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, 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, 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. 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 in this specification. 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, unless otherwise specified in this specification. 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, 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, 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.

[0019] "Substituted or unsubstituted aryl groups" 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 unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, when the term "aryl group" is simply used, it includes both an "unsubstituted aryl group" and a "substituted aryl group". The term "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 the "unsubstituted aryl group" in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B 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 the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom bonded to a carbon atom of the aryl group itself is further replaced with a substituent, and the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom of a substituent is further replaced with a substituent.

[0020] 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, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group, A triphenylenyl group, Benzotriphenylenyl group, tetracenyl group, Pentacenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, 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 formulas (TEMP-1) to (TEMP-15).

[0021] [ka]

[0022] [ka]

[0023] 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 group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, 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.

[0024] "Substituted or unsubstituted heterocyclic groups" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom as a ring-forming atom. 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, when the term "heterocyclic group" is simply used, it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". The term "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 the hydrogen atoms of the "unsubstituted heterocyclic group" in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes the groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent, and the groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent.

[0025] The 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).

[0026] Specific example group G2B includes, for example, the following nitrogen atom-containing substituted heterocyclic groups (specific example group G2B1), oxygen atom-containing substituted heterocyclic groups (specific example group G2B2), sulfur atom-containing substituted heterocyclic groups (specific example group G2B3), and monovalent heterocyclic groups derived from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33), in which one or more hydrogen atoms are replaced with substituents (specific example group G2B4).

[0027] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, pyrimidinyl group, A pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, A quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl group, A phenanthridinyl group, acridinyl group, A phenazinyl group, A carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, A phenothiazinyl group, Azacarbazolyl and diazacarbazolyl groups.

[0028] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl groups, and Diazanaphthobenzofuranyl group.

[0029] 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, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0030] 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):

[0031] [ka]

[0032] [ka]

[0033] 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 formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0034] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0035] 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].

[0036] 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].

[0037] 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):

[0038] The above "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 CH2.

[0039] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification 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 the term "alkyl group" is simply mentioned, it includes both the "unsubstituted alkyl group" and the "substituted alkyl group". The term "substituted alkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are 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 are replaced with a substituent, and 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 straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of 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 the 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 the specific example group G3B is further replaced with a substituent.

[0040] 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.

[0041] Substituted alkyl groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0042] "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "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". The term "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent.

[0043] Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, 2-butenyl group, and 3-Butenyl group.

[0044] Substituted alkenyl groups (specific example group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-Dimethylallyl group.

[0045] "Substituted or unsubstituted alkynyl groups" 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 the 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". The term "substituted alkynyl group" refers to an "unsubstituted alkynyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include the following "unsubstituted alkynyl groups" (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.

[0046] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group

[0047] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification 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". The term "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are 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 are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" in the specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself are replaced with a substituent, and a group in the "substituted cycloalkyl group" in the specific example group G6B in which a hydrogen atom of a substituent is further replaced with a substituent.

[0048] Unsubstituted cycloalkyl groups (specific example group G6A): A cyclopropyl group, A cyclobutyl group, Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-Norbornyl group.

[0049] Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl group.

[0050] -Si(R 901 )(R 902 )(R 903 ) a group represented by As described herein, -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 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) are the same as or different from each other.

[0051] -O-(R 904 ) a group represented by As described herein, -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 specific example group G6.

[0052] -S-(R 905 ) a group represented by As described herein, -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 specific example group G6.

[0053] -N(R 906 )(R 907 ) a group represented by As described herein, -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 specific example group G6. -The multiple G1's in N(G1)(G1) are the same or different from each other. -The multiple G2's in N(G2)(G2) are the same or different from each other. -The multiple G3's in N(G3)(G3) are the same or different from each other. -N(G6)(G6) may be the same or different.

[0054] "Halogen atoms" Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0055] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "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 in the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a fluorine atom.

[0056] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "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 the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "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 the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

[0057] "Substituted or unsubstituted alkoxy groups" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0058] "Substituted or unsubstituted alkylthio groups" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0059] "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.

[0060] "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.

[0061] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are the same or different from each other. 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, unless otherwise specified in this specification.

[0062] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification 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, the "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 aspect of a "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in the present specification. 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.

[0063] 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, a 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, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a 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, and the like.

[0064] The substituted or unsubstituted heterocyclic group described in the present specification, unless otherwise specified in the present specification, 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 of such groups 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.

[0065] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in the specification.

[0066] [ka]

[0067] In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise specified in the specification.

[0068] [ka]

[0069] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0070] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0071] [ka]

[0072] In the above general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0073] The substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like, unless otherwise specified herein.

[0074] "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.

[0075] "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 of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) 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.

[0076] "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.

[0077] The substituted or unsubstituted arylene group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0078] [ka]

[0079] [ka]

[0080] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the above general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0081] [ka]

[0082] 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 above general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0083] [ka]

[0084] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the above general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0085] The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[0086] [ka]

[0087] [ka]

[0088] [ka]

[0089] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

[0095] The above is an explanation of "the substituents described in this specification".

[0096] - "When bonded to form a ring" In this specification, the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other". In this specification, the cases where "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "a case where they are bonded 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 mother skeleton is an anthracene ring, will be explained as an example.

[0097] [ka]

[0098] 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 With R 922 and R 923 With R 923 and R 924 With R 924 and R 930 With R 930 and R 925 With R 925 and R 926 With R 926 and R 927 With R 927 and R 928 With R 928 and R 929 and R 929 and R 921 It is paired with .

[0099] 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 ring Q A At the same time, R 925 and R 926 and are bonded to ring Q B When the above 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).

[0100] [ka]

[0101] The case where a "set of two or more adjacent units" forms a ring includes not only the case where a set of two adjacent units is bonded as in the previous example, but also the case where a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to ring Q A and R 922 and R923 and are bonded to ring Q C The 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). In the following general formula (TEMP-105), the ring Q A and Ring Q C is R 922 Share.

[0102] [ka]

[0103] The "monocyclic ring" or "condensed ring" formed may be a saturated or unsaturated ring as the structure of only the ring formed. Even when "one of the pairs of adjacent two" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or the "condensed ring" may form a saturated or unsaturated ring. For example, the ring Q formed in the general formula (TEMP-104) may be a saturated or unsaturated ring. A and Ring Q B are "monocyclic" or "condensed rings". In addition, the ring Q formed in the general formula (TEMP-105) A , and ring Q C is a "fused ring". The ring Q in the above general formula (TEMP-105) A and Kan Q C That is, Ring Q A and Kan Q C The ring Q in the general formula (TMEP-104) is condensed to form a condensed 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.

[0104] The "unsaturated ring" includes aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond in the ring structure, i.e., a double bond and / or a triple bond (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring having no unsaturated bond, or a non-aromatic heterocycle having no unsaturated bond. 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 "form a ring" means that a ring is formed only with a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more optional atoms. For example, R 921 and R 922 and are bonded together to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary atoms. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When the carbon atom of the anthracene skeleton to which R is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 and R 922 The ring formed by this is a benzene ring.

[0105] Here, unless otherwise specified in the present specification, the "arbitrary atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In the arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary atom other than a carbon atom is included, the ring formed is a heterocycle. Unless otherwise specified in this specification, the "any one or more atoms" constituting the single ring or the condensed 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 "condensed 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 in this specification, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more of a set of two or more adjacent rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more of a set of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0106] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned 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 "condensed 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 with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring" ("combined to form a ring").

[0107] Substituents in the phrase "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) is, 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, Here, 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 or different from each other, R 902 If there are two or more, there are two or more R 902 are identical or different from each other, R 903 If there are two or more, there are two or more R 903 are identical or different from each other, R 904 If there are two or more, there are two or more R 904 are identical or different from each other, R 905 If there are two or more, there are two or more R 905 are identical or different from each other, R 906 If there are two or more, there are two or more R 906 are identical 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.

[0108] In one embodiment, the substituent in the above "substituted or unsubstituted" is: 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:

[0109] In one embodiment, the substituent in the above "substituted or unsubstituted" is: 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:

[0110] 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."

[0111] Unless otherwise specified in this specification, any adjacent substituents may be combined with 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 the present specification, the optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0112] In this specification, a numerical range expressed using "AA to BB" means a range including 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.

[0113] [New compounds] A compound according to one embodiment of the present invention is a compound represented by the following formulas (1-1) and (1-3), or a compound represented by the following formulas (1-2) and (1-3). [ka] (In the formula (1-1), the formula (1-2) and the formula (1-3), Ring A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. The two bonds * in the formula (1-1) are each bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring of the ring A or a ring-forming atom of the heterocycle. The three bonds * in the formula (1-2) are bonded to ring-forming carbon atoms of the aromatic hydrocarbon ring of the ring A or to ring-forming atoms of the heterocycle. R1~R 16 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The R to R do not form a substituted or unsubstituted saturated or unsaturated ring. 16 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. In the compounds represented by the formula (1-1) and the formula (1-3), R5 to R7 and R 14 ~R 16 At least one of -N(R 36 )(R 37 In the compounds represented by the formulas (1-2) and (1-3), R to R 16 At least one of -N(R 36 )(R 37 ). R1~R 16 At least one pair of adjacent two or more of R to R 16at least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms (hereinafter sometimes referred to as substituent A). R 31 ~R 37 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 31 ~R 37 If there are multiple of each of them, there are multiple R 31 ~R 37 may be the same or different.)

[0114] By using the compound according to one embodiment of the present invention, an organic EL device having a long life can be manufactured.

[0115] "R1~R 16 may form a substituted or unsubstituted saturated or unsaturated ring”. "R1~R 16"A pair of two or more adjacent ones of" refers to, for example, combinations of R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R1, R2 and R3, etc. The substituents in the "substituted" portion of the "substituted or unsubstituted" portion of the saturated or unsaturated ring are the same as those in the "substituted or unsubstituted" portion described below. In general, in the compounds represented by the formulas (1-2) and (1-3), R8 and R9 do not bond to each other to form a single bond.

[0116] The term "saturated or unsaturated ring" refers to, for example, when R1 and R2 form a ring, the ring is formed by the carbon atom to which R1 is bonded, the carbon atom to which R2 is bonded, and one or more arbitrary atoms. Specifically, when R1 and R2 form a ring, when the carbon atom to which R1 is bonded, the carbon atom to which R2 is bonded, and four carbon atoms form an unsaturated ring, the ring formed by R1 and R2 is a benzene ring.

[0117] The "arbitrary atom" is preferably a C atom, an N atom, an O atom, or an S atom. In any atom (for example, in the case of a C atom or an N atom), a bond that does not form a ring may be terminated with a hydrogen atom or the like. The "any one or more atoms" refers to any number of atoms, 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. Hereinafter, the expression "one or more pairs of two or more adjacent ones of X to Y may form a substituted or unsubstituted saturated or unsaturated ring" refers to X being the above R1 and Y being the above R 16 This has the same meaning as when replaced with

[0118] The "*" (asterisk) in formula (1-1) is a bond that bonds to ring A in formula (1-3). There are two "*"s in formula (1-1), and the two "*"s are bonded to ring-forming carbon atoms of the aromatic hydrocarbon ring of ring A or ring-forming atoms of the heterocycle, respectively, to form a compound. The "*" (asterisk) in formula (1-2) is also a bond to ring A in formula (1-3). There are three "*"s in formula (1-2), and the three "*"s are bonded to ring-forming carbon atoms of the aromatic hydrocarbon ring of ring A or ring-forming atoms of the heterocycle, respectively, to form a compound.

[0119] In one embodiment, the ring A is a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, a substituted or unsubstituted heterocycle having 5 to 50 ring atoms, or a benzene ring represented by the following formula (2): [ka] (In the formula (2), One of the two ring-forming carbon atoms marked with * is bonded to a bond extending from the benzene ring B in the formula (1-1) or (1-2), and the other is bonded to a bond extending from the benzene ring C in the formula (1-3). R 17 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 31 ~R 37are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 31 ~R 37 If there are multiple of each of them, there are multiple R 31 ~R 37 may be the same or different. n is an integer of 1 or 2. When n is 2, two R 17 may be the same or different.)

[0120] In the above-mentioned embodiment, the two bonds * in the formula (1-1) are each bonded to a ring-forming carbon atom of the fused aromatic hydrocarbon ring of the ring A, a ring-forming atom of the heterocycle, or a ring-forming carbon atom of the benzene ring represented by the formula (2). In the above-mentioned embodiment, the three bonds * in the formula (1-2) are each bonded to a ring-forming carbon atom of the fused aromatic hydrocarbon ring of the ring A, a ring-forming atom of the heterocycle, or a ring-forming carbon atom of the benzene ring represented by the formula (2).

[0121] A fused aromatic hydrocarbon ring is a ring in which multiple aromatic rings are fused together. For example, biphenyl, which has two aromatic rings bonded together by a single bond, is not included in the fused aromatic hydrocarbon ring.

[0122] In the compounds represented by the formulas (1-1) and (1-3) and the compounds represented by the following formulas (1-2) and (1-3), R1 to R 16 At least one pair of adjacent two or more of R to R 16 At least one of these is a specific group (substituent A).

[0123] R1 to R2 do not form a substituted or unsubstituted saturated or unsaturated ring and are not the substituent A. 16are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0124] In one embodiment, R to R do not form a substituted or unsubstituted saturated or unsaturated ring and are not the substituent A. 16 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0125] In one embodiment, in the compounds represented by formulas (1-1) and (1-3), R1 to R4, R 10 ~R 13 At least one of R1, R3, R 10 , and R 12 At least one of R3 and R4 is a substituent A. 12 may each independently be a substituent A, and R and R 10 may each independently be a substituent A. In one embodiment, in the compounds represented by formulas (1-2) and (1-3), R2 to R4, R9 to R 13 At least one of these is a substituent A.

[0126] In one embodiment, the substituent A is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 ring carbon atoms, -Si(R 31 )(R 32 )(R 33 ), a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. The number of carbon atoms in the alkyl group may be 1 to 30, 1 to 18, or 1 to 5.

[0127] In one embodiment, in the compounds represented by the formula (1-1) and the formula (1-3), R and R 14 At least one of (e.g., R5 and R 14 Both) are -N(R 36 )(R 37 ).

[0128] In one embodiment, in the compounds represented by the formula (1-2) and the formula (1-3), R5 to R8 and R 14 ~R 16 At least one of -N(R 36 )(R 37 ), preferably R and R 14 At least one of -N(R 36 )(R 37 ).

[0129] In one embodiment, R 36 and R 37 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. In this case, R 36 and R 37 All or a part of the hydrogen atoms contained in may be deuterium atoms.

[0130] In one embodiment, R 36 and R 37 are each independently a substituted or unsubstituted phenyl group. All or a part of the hydrogen atoms contained in the phenyl group may be deuterium atoms.

[0131] In one embodiment, examples of the substituent of the aryl group having 6 to 50 ring carbon atoms (e.g., a phenyl group) or the monovalent heterocyclic group having 5 to 50 ring atoms include an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 12 carbon atoms (e.g., a phenyl group or a naphthyl group), and for example, the phenyl group may be substituted with both an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 12 carbon atoms. In addition, all or a part of the hydrogen atoms contained in the aryl group having 6 to 12 carbon atoms may be deuterium atoms.

[0132] In general, in the compounds represented by the formulas (1-1) and (1-3) or the compounds represented by the formulas (1-2) and (1-3), R 36 and R 37 is R1~R 16 does not bond to form a ring.

[0133] In one embodiment, the compounds represented by the formulas (1-1) and (1-3), or the compounds represented by the formulas (1-2) and (1-3) are compounds represented by the following formula (3), formula (4), formula (5), or formula (7). [ka] (In the formula (3), the formula (4), the formula (5) and the formula (7), Ring A' is a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. R1~R 17 is as defined in the formula (1-1), the formula (1-2), the formula (1-3) and the formula (2).

[0134] In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring.

[0135] In one embodiment, the substituted or unsubstituted heterocycle having 5 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[0136] In one embodiment, the compounds represented by formulas (1-1) and (1-3) are selected from the group consisting of compounds represented by formulas (6-1) to (6-31) below. [ka] [ka] [ka] [ka] (In the formulas (6-1) to (6-31), R1 to R7 and R 10 ~R 17 is as defined in the formula (1-1), the formula (1-2), the formula (1-3) and the formula (2). X is O, S, or NR 25 , or C(R 26 )(R 27 ). R 21 ~R 27 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The substituted or unsubstituted R which does not form a saturated or unsaturated ring 21 ~R 27 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R31 ~R 37 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 31 ~R 37 If there are multiple of each of them, there are multiple R 31 ~R 37 may be the same or different.)

[0137] In one embodiment, the compounds represented by formulas (1-2) and (1-3) are compounds represented by formula (7-1): [ka] (In the above formula (7-1), R2~R 13 and R 15 ~R 16 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The R to R do not form a substituted or unsubstituted saturated or unsaturated ring. 13 and R 15 ~R 16 , and R 17 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R2~R 13 and R 15 ~R 16 At least one pair of adjacent two or more of R to R 13 and R 15 ~R 16 at least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R A and R B are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0138] In one embodiment, the compounds represented by formulas (1-2) and (1-3) are compounds represented by formula (7-2): [ka] (In the formula (7-2), R2 to R4 and R6 to R 16 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The R2 to R4 and R6 to R6 do not form a substituted or unsubstituted saturated or unsaturated ring. 16 , and R 17 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R2 to R4 and R6 to R 16 Among these, one or more pairs of adjacent two or more of R to R form a substituted or unsubstituted saturated or unsaturated ring, or R to R and R to R 16at least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R C and R D are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0139] In one embodiment, the compounds represented by formulas (1-2) and (1-3) are compounds represented by formula (7-3): [ka] (In the above formula (7-3), R2~R4, R6~R 13 and R 15 ~R 16 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The R2 to R4 and R6 to R6 do not form a substituted or unsubstituted saturated or unsaturated ring. 13 and R 15 ~R 16 , and R 17each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R2~R4, R6~R 13 and R 15 ~R 16 Among these, one or more pairs of adjacent two or more of R to R form a substituted or unsubstituted saturated or unsaturated ring, or 13 and R 15 ~R 16 at least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34, -COOR 35 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R A , R B , R C and R D are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0140] In one embodiment, the compounds represented by formulas (1-1) and (1-3) are compounds represented by formula (8): [ka] (In the formula (8), R1 to R4, R6 to R7 and R 10 ~R 16 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The above-mentioned R1 to R4, R6 to R7 and R 10 ~R 16 , and R 17 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 17 may be the same as or different from each other. R1 to R4, R6 to R7 and R 10 ~R 16 Among these, one or more pairs of adjacent two or more of R1 to R4, R6 to R7 and R 10 ~R 16 at least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R A and R B are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0141] In one embodiment, the compounds represented by formulas (1-1) and (1-3) are compounds represented by formula (9): [ka] (In the formula (9), R1~R4, R6~R7, R 10 ~R 13 and R 15 ~R 16 One or more pairs of adjacent two or more of these may form a substituted or unsubstituted saturated or unsaturated ring. The above-mentioned R1 to R4, R6 to R7, and R 10 ~R 13 and R 15 ~R 16 , and R 17 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , -N(R 36 )(R 37 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 17 may be the same as or different from each other. R1~R4, R6~R7, R 10 ~R 13 and R 15 ~R 16 Among these, one or more pairs of adjacent two or more of R1 to R4, R6 to R7, R10 ~R 13 and R 15 ~R 16 at least one of the above is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 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, -Si(R 31 )(R 32 )(R 33 ), -C(=O)R 34 , -COOR 35 , a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R A , R B , R C and R D are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0142] In one embodiment, the compound represented by formula (9) is a compound represented by the following formula (9-1): [ka] (In the above formula (9-1), R1~R4, R 10 ~R 13 , R 17 , R A , R B , R C and R D is as defined in the above formula (9).

[0143] In one embodiment, the compound represented by formula (9) is a compound represented by formula (9-2) below. [ka] (In the formula (9-2), R3, R 12 , R 17 , R A , R B , R C and R D is as defined in the above formula (9).

[0144] In one embodiment, the compound represented by formula (9) is a compound represented by the following formula (9-3): [ka] (In the formula (9-3), R1, R 10 , R 17 , R A , R B , R C and R D is as defined in the above formula (9).

[0145] In general, in the compounds represented by the formulas (7-1), (7-2), (7-3), (8), (9), (9-1), (9-2), and (9-3), R A and R B , and R C and R D is R1~R 17 , and R 31 ~R 37 does not bond to form a ring.

[0146] In one embodiment, R A , R B , R C and R D each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0147] In one embodiment, R A , R B , R C and R D are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, R A , R B , R C and R D All or some of the hydrogen atoms contained in are deuterium atoms.

[0148] In one embodiment, R A , R B , R C and R D are each independently a substituted or unsubstituted phenyl group. All or a part of the hydrogen atoms contained in the phenyl group may be deuterium atoms.

[0149] In one embodiment, examples of the substituent of the aryl group having 6 to 50 ring carbon atoms (e.g., a phenyl group) or the monovalent heterocyclic group having 5 to 50 ring atoms include an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 12 carbon atoms (e.g., a phenyl group or a naphthyl group), and for example, the phenyl group may be substituted with both an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 12 carbon atoms. In addition, all or a part of the hydrogen atoms contained in the aryl group having 6 to 12 carbon atoms may be deuterium atoms.

[0150] In one embodiment, R A , R B , R C and R D are each independently a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms, a phenyl group substituted with an aryl group having 6 to 12 carbon atoms, a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 12 carbon atoms, or an unsubstituted phenyl group.

[0151] In one embodiment, R A and R B Combination with (R A , R BExamples of the phenyl group include (unsubstituted phenyl group, unsubstituted phenyl group), (unsubstituted phenyl group, phenyl group substituted with an alkyl group having 1 to 5 carbon atoms), (phenyl group substituted with an alkyl group having 1 to 5 carbon atoms, phenyl group substituted with an alkyl group having 1 to 5 carbon atoms), (unsubstituted phenyl group, phenyl group substituted with an aryl group having 6 to 12 carbon atoms), (phenyl group substituted with an alkyl group having 1 to 5 carbon atoms, phenyl group substituted with an aryl group having 6 to 12 carbon atoms), (phenyl group substituted with an aryl group having 6 to 12 carbon atoms, phenyl group substituted with an aryl group having 6 to 12 carbon atoms), (unsubstituted phenyl group, phenyl group substituted with an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 12 carbon atoms), and the like. R C and R D Combination with (R C , R D ) is the above R A and R B Combination with (R A , R B ) are the same as

[0152] In one embodiment, R 17 are hydrogen atoms.

[0153] In the compounds represented by formulae (1-1) and (1-3), and the compounds represented by formulae (1-2) and (1-3), the substituent in the case of being "substituted or unsubstituted" is an alkyl group having 1 to 50 carbon atoms, a haloalkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, an aralkyl group having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 ), -C(=O)R 44 , -COOR 45 , -S(=O)2R 46 , -P(=O)(R 47 )(R 48 ), -Ge(R49 )(R 50 )(R 51 ), -N(R 52 )(R 53 ) (where R 41 ~R 53 R are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms. 41 ~R 53 If there are two or more, there are two or more R 41 ~R 53 may be the same or different.) is selected from the group consisting of a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms.

[0154] In one embodiment, the substituent in the compounds represented by formulae (1-1) and (1-3) and the compounds represented by formulae (1-2) and (1-3) when referred to as "substituted or unsubstituted" is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms.

[0155] In one embodiment, the substituent in the compounds represented by formulae (1-1) and (1-3) and the compounds represented by formulae (1-2) and (1-3) when referred to as "substituted or unsubstituted" is selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, and a monovalent heterocyclic group having 5 to 30 ring atoms.

[0156] In one embodiment, the substituent in the compounds represented by formulae (1-1) and (1-3) and the compounds represented by formulae (1-2) and (1-3) when referred to as "substituted or unsubstituted" is selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring atoms.

[0157] Specific examples of the substituents, and the substituents and halogen atoms in the compounds represented by formulae (1-1) and (1-3) and the compounds represented by formulae (1-2) and (1-3), in the case of being "substituted or unsubstituted", are the same as those described above.

[0158] The compounds represented by formulae (1-1) and (1-3), or the compounds represented by formulae (1-2) and (1-3) can be synthesized by following the examples and using known alternative reactions and raw materials suited to the target compound.

[0159] Specific examples of the compounds represented by formulae (1-1) and (1-3) or (1-2) and (1-3) are given below, but these are merely illustrative and the compounds represented by formulae (1-1) and (1-3) or (1-2) and (1-3) are not limited to the following specific examples. In the following specific examples, Me represents a methyl group and Ph represents a phenyl group.

[0160] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0161] [Materials for organic electroluminescence devices] INDUSTRIAL APPLICABILITY The compound according to one embodiment of the present invention is useful as a material for an organic EL device, and is useful as a material for the light-emitting layer of an organic EL device, and is particularly useful as a dopant material for the light-emitting layer. By using the compound according to one embodiment of the present invention in the light-emitting layer of an organic EL device, it is possible to obtain an organic EL device having a long life.

[0162] [Organic EL element] An organic EL device according to one embodiment of the present invention includes a cathode, an anode, and at least one organic layer disposed between the cathode and the anode, and at least one of the at least one organic layer contains the compounds represented by formulas (1-1) and (1-3) or the compounds represented by formulas (1-2) and (1-3).

[0163] The schematic configuration of an organic EL device according to one embodiment of the present invention will be described with reference to FIG. An organic EL device 1 according to one embodiment of the present invention includes a substrate 2, an anode 3, an organic light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. Each of the organic layer 4 and the organic layer 6 may be a single layer or may be composed of multiple layers. The organic layer 4 may also include a hole transport region. The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, etc. The organic layer 6 may also include an electron transport region. The electron transport region may include an electron injection layer, an electron transport layer, a hole blocking layer, etc. The compounds represented by the formulas (1-1) and (1-3) or the compounds represented by the formulas (1-2) and (1-3) are contained in the organic layer 4, the light-emitting layer 5, or the organic layer 6. In one embodiment, the compounds represented by the formulas (1-1) and (1-3) or the compounds represented by the formulas (1-2) and (1-3) are contained in the light-emitting layer 5. The compounds represented by the formulas (1-1) and (1-3) or the compounds represented by the formulas (1-2) and (1-3) can function as a dopant material in the light-emitting layer 5.

[0164] In an organic EL device according to one embodiment of the present invention, at least one of the at least one organic layer contains a first compound and a second compound that are not identical to each other, and the first compound is a compound represented by formulas (1-1) and (1-3) or a compound represented by formulas (1-2) and (1-3).

[0165] In the organic EL device according to one embodiment of the present invention, the second compound is a heterocyclic compound or a fused aromatic compound. In the organic EL device according to one embodiment of the present invention, the second compound is an anthracene derivative.

[0166] In the organic EL device according to one embodiment of the present invention, the second compound is a compound represented by the following formula (10).

[0167] <Compound represented by formula (10)> The compound represented by formula (10) will be described.

[0168] [ka]

[0169] [In formula (10), R 101 ~R 110 one or more pairs of adjacent two or more of the above groups form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. The substituted or unsubstituted R which does not form a saturated or unsaturated ring 101 ~R 110 are each independently Hydrogen atoms, A substituent R, or It is a group represented by the following formula (11). -L 101 -Ar 101 (11)

[0170] (In formula (11), L101 teeth, Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms. Ar 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more of the substituents R are present, the two or more substituents R may be the same or different. 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 monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. However, R does not form a substituted or unsubstituted saturated or unsaturated ring. 101 ~R 110 At least one of the formulas (11) is a group represented by the formula (11). When two or more formulas (11) are present, the two or more groups represented by the formulas (11) may be the same or different. The compound represented by the above formula (10) may have a deuterium atom in place of a hydrogen atom.

[0171] In one embodiment, Ar in formula (10) 101 At least one of these is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0172] In one embodiment, Ar in formula (10) 101 At least one of the above is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0173] In one embodiment, all of Ar in formula (10) 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 101 may be the same as or different from each other.

[0174] In one embodiment, Ar in formula (10) 101 one of the Ar is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, and the remaining Ar 101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 101 may be the same as or different from each other.

[0175] In one embodiment, L in formula (10)101 At least one of is a single bond. In one embodiment, L in formula (10) 101 are all single bonds. In one embodiment, L in formula (10) 101 At least one of these is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. In one embodiment, L in formula (10) 101 At least one of these is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthyl group.

[0176] In one embodiment, -L in formula (10) 101 -Ar 101 The group represented by a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and It is selected from the group consisting of substituted or unsubstituted carbazolyl groups.

[0177] In one embodiment, the substituents R in the formula (10) are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R 901 ~R 907 is as defined in the above formula (10).

[0178] In one embodiment, the "substituted or unsubstituted" substituents in the formula (10) are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 is as defined in the above formula (10).

[0179] In one embodiment, the "substituted or unsubstituted" substituents in the formula (10) are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901)(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R 901 ~R 907 is as defined in the above formula (10).

[0180] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the formula (10) is an alkyl group having 1 to 18 carbon atoms; An aryl group having 6 to 18 ring carbon atoms, and It is selected from the group consisting of monovalent heterocyclic groups having 5 to 18 ring atoms.

[0181] In one embodiment, the substituent in the "substituted or unsubstituted" in the formula (10) is an alkyl group having 1 to 5 carbon atoms.

[0182] In one embodiment, the compound represented by formula (10) is a compound represented by formula (20):

[0183] [ka]

[0184] (In formula (20), R 101 ~R 108 , L 101 and Ar 101 is as defined in the above formula (10). The compound represented by the above formula (20) may have a deuterium atom in place of a hydrogen atom.

[0185] That is, in one embodiment, the compound represented by the formula (10) or (20) has at least two groups represented by the formula (11). In one embodiment, the compound represented by formula (10) or formula (20) has two or three groups represented by formula (11).

[0186] In one embodiment, R in formulas (10) and (20) 101 ~R 110 does not form a substituted or unsubstituted saturated or unsaturated ring. In one embodiment, R in formulas (10) and (20) 101 ~R 110 is a hydrogen atom.

[0187] In one embodiment, in the compound represented by formula (20), Ar 101 At least one of the above is a monovalent group having a structure represented by the following formula (50).

[0188] [ka]

[0189] (In formula (50), X 151 is O, S or C(R 161 )(R 162 ). R 151 ~R 160 One of them is L 101 It is a single bond that bonds to L 101 R is not a single bond that bonds with 151 ~R 154 Two or more adjacent ones of and R 155 ~R 160 one or more pairs of adjacent two or more of the above may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring. R 161 and R 162are bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring. The substituted or unsubstituted R which does not form a saturated or unsaturated ring 161 and R 162 , and L 101 R which is not a single bond bonded to and does not form the substituted or unsubstituted saturated or unsaturated ring 151 ~R 160 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (10). Ar which is not a monovalent group having the structure represented by the formula (50) 101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0190] L in the above formula (50) 101 The position of the single bond with is not particularly limited. In one embodiment, R in formula (50) 151 ~R 154 or R 155 ~R 160 One of them is L 101 It is a single bond that bonds to

[0191] In one embodiment, Ar 101 However, the following formula (50-R 152 ), (50-R 153 ), (50-R 154 ), (50-R 157 ) or (50-R 158 ) is a monovalent group represented by the formula: [ka]

[0192] (Formula(50-R 152 ), (50-R 153 ), (50-R 154), (50-R 157 ) and (50-R 158 ), X 151 , R 151 ~R 160 is as defined in the above formula (50). *L 101 )

[0193] In one embodiment, the compound represented by formula (20) is a compound represented by formula (30):

[0194] [ka]

[0195] (In formula (30), L 101 and Ar 101 is as defined in the above formula (10). R 101A ~R 108A adjacent two of these do not form a substituted or unsubstituted saturated or unsaturated ring. R 101A ~R 108A are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10).

[0196] That is, the compound represented by the above formula (30) is a compound having two groups represented by the above formula (11). The compound represented by the above formula (30) contains substantially only proton atoms as hydrogen atoms. Incidentally, "having substantially only protium atoms" means that the proportion of protium atoms to the total of a compound having only protium atoms as hydrogen atoms (protium atoms) and a compound having deuterium atoms (deuterium atoms) that have the same structure is 90 mol % or more, 95 mol % or more, or 99 mol % or more.

[0197] In one embodiment, the compound represented by formula (30) is a compound represented by formula (31):

[0198] [ka]

[0199] (In formula (31), L 101 and Ar 101 is as defined in the above formula (10). R 101A ~R 108A is as defined in the above formula (30). X b is O, S, N(R 131 ), or C(R 132 )(R 133 ). R 121 ~R 128 , and R 131 ~R 133 One of them is L 101 It is a single bond that bonds to L 101 R that is not a single bond 121 ~R 128 one or more pairs of adjacent two or more of the above groups form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. L 101 R which is not a single bond bonded to and does not form the substituted or unsubstituted saturated or unsaturated ring 121 ~R 128 are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10). L 101 R that is not a single bond 131 ~R 133 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 monovalent heterocyclic group having 5 to 50 ring atoms. R 131 ~R 133 If there are two or more, there are two or more R 131 ~R 133 may be the same or different.)

[0200] In one embodiment, the compound represented by formula (31) is a compound represented by formula (32):

[0201] [ka]

[0202] (In formula (32), R 101A ~R 108A , L 101 , Ar 101 , R 121 ~R 128 , R 132 and R 133 is as defined in the above formula (31).

[0203] In one embodiment, the compound represented by formula (31) is a compound represented by formula (33):

[0204] [ka]

[0205] (In formula (33), R 101A ~R 108A , L 101 , Ar 101 , and R 121 ~R 128 is as defined in the above formula (31). X c is O, S, or NR 131 It is. R 131 is as defined in the above formula (31).

[0206] In one embodiment, the compound represented by formula (31) is a compound represented by formula (34):

[0207] [ka]

[0208] (In formula (34), R 101A ~R 108A , L 101 and Ar 101 is as defined in the above formula (31). X c is O, S or NR 131 It is. R 131 is as defined in the above formula (31). R 121A ~R 128A One of them is L 101 It is a single bond that bonds to L 101 R that is not a single bond 121A ~R 128A At least one pair of adjacent two or more of the above does not form a substituted or unsubstituted saturated or unsaturated ring. L 101 R that is not a single bond 121A ~R 128A are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10).

[0209] In one embodiment, the compound represented by formula (31) is a compound represented by formula (35):

[0210] [ka]

[0211] [In formula (35), R 101A ~R 108A , L 101 , Ar101 and X b is as defined in the above formula (31). R 121A ~R 124A one or more pairs of two or more adjacent groups among R 125B and R 126B , R 126B and R 127B , and R 127B and R 128B Any one pair of these is bonded to each other to form a ring represented by the following formula (35a) or (35b).

[0212] [ka]

[0213] (In formulas (35a) and (35b), The two * are R 125B and R R126B , R 126B and R 127B , and R 127B and R 128B It combines with one of the following pairs. R 141 ~R 144 are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10). X d is O or S. R 121A ~R 124A R which does not form a ring represented by the formula (35a) or (35b) 125B ~R 128B , and R 141 ~R 144 One of them is L 101 It is a single bond that bonds to L 101 R that is not a single bond 121A ~R 124A , and L 101R which is not a single bond bonded to and does not form a ring represented by formula (35a) or (35b) 125B ~R 128B are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10).

[0214] In one embodiment, the compound represented by formula (35) is a compound represented by formula (36):

[0215] [ka]

[0216] (In formula (36), R 101A ~R 108A , L 101 , Ar 101 , and R 125B ~R 128B is as defined in the above formula (35).

[0217] In one embodiment, the compound represented by formula (34) is a compound represented by formula (37):

[0218] [ka]

[0219] (In formula (37), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is as defined in the above formula (34).

[0220] In one embodiment, R in the formulas (30) to (37) 101A ~R 108A is a hydrogen atom.

[0221] In one embodiment, the compound represented by formula (10) is a compound represented by formula (40):

[0222] [ka]

[0223] (In formula (40), L 101 and Ar 101 is as defined in the above formula (10). R 101A , and R 103A ~R 108A one or more pairs of adjacent two or more of the above groups form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. The substituted or unsubstituted R which does not form a saturated or unsaturated ring 101A , and R 103A ~R 108A are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10). That is, the compound represented by the formula (40) is a compound having three groups represented by the formula (11). Moreover, the compound represented by the formula (40) has substantially only proton atoms as hydrogen atoms.

[0224] In one embodiment, the compound represented by formula (40) is represented by the following formula (41).

[0225] [ka]

[0226] (In formula (41), L 101 and Ar 101 is as defined in the above formula (40).

[0227] In one embodiment, the compound represented by formula (40) is a compound represented by any one of the following formulas (42-1) to (42-3).

[0228] [ka]

[0229] (In formulas (42-1) to (42-3), R 101A ~R 108A , L 101 and Ar 101 is as defined in the above formula (40).

[0230] In one embodiment, the compounds represented by the above formulas (42-1) to (42-3) are compounds represented by any of the following formulas (43-1) to (43-3).

[0231] [ka]

[0232] (In formulas (43-1) to (43-3), L 101 and Ar 101 is as defined in the above formula (40).

[0233] In one embodiment, -L in the formulas (40), (41), (42-1) to (42-3), and (43-1) to (43-3) 101 -Ar 101 The group represented by a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and It is selected from the group consisting of substituted or unsubstituted carbazolyl groups.

[0234] In one embodiment, the compounds represented by formula (10) or (20) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom.

[0235] In one embodiment, in the formula (20), R is a hydrogen atom 101 ~R 108 , The substituent R is R 101 ~R 108 a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents At least one of the is a deuterium atom.

[0236] The compounds represented by the formulas (30) to (37) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom. In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compounds represented by the formulas (30) to (37) is a deuterium atom.

[0237] In one embodiment, the compound represented by formula (30) is a compound represented by formula (30D):

[0238] [ka]

[0239] (In formula (30D), R 101A ~R 108A , L 101 and Ar 101 is as defined in the above formula (30). However, R is a hydrogen atom. 101A ~R 110A , The substituent R is R 101A ~R 110A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents At least one of the is a deuterium atom.) That is, the compound represented by the above formula (30D) is a compound in which at least one of the hydrogen atoms of the compound represented by the above formula (30) is a deuterium atom.

[0240] In one embodiment, R which is a hydrogen atom in formula (30D) 101A ~R 108A At least one of the is a deuterium atom.

[0241] In one embodiment, the compound represented by formula (30D) is a compound represented by formula (31D):

[0242] [ka]

[0243] (In formula (31D), R 101A ~R 108A , L 101 and Ar 101 is as defined in formula (30D) above. X d is O or S. R 121 ~R 128 One of them is L101 It is a single bond that bonds to L 101 R that is not a single bond 121 ~R 128 one or more pairs of adjacent two or more of the above may form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring. L 101 R which is not a single bond bonded to and does not form the substituted or unsubstituted saturated or unsaturated ring 121 ~R 128 are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10). However, R is a hydrogen atom. 101A ~R 110A , The substituent R is R 101A ~R 110A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 Hydrogen atoms of the substituents R is a hydrogen atom 121 ~R 128 , and The substituent R is R 121 ~R 128 Hydrogen atoms possessed by At least one of the is a deuterium atom.)

[0244] In one embodiment, the compound represented by formula (31D) is a compound represented by formula (32D):

[0245] [ka]

[0246] (In formula (32D), R101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is as defined in formula (31D) above. however, R is a hydrogen atom 101A ~R 108A , The substituent R is R 101A ~R 108A a hydrogen atom possessed by R is a hydrogen atom 125A ~R 128A , The substituent R is R 125A ~R 128A a hydrogen atom possessed by A hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in formula (32D), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents At least one of the is a deuterium atom.)

[0247] In one embodiment, the compound represented by formula (32D) is a compound represented by the following formula (32D-1) or (32D-2).

[0248] [ka]

[0249] (In formulas (32D-1) and (32D-2), R 101A ~R 108A , R 125A ~R 128A , L 101 and Ar 101 is as defined in formula (32D) above. however, R is a hydrogen atom 101A ~R108A , The substituent R is R 101A ~R 108A a hydrogen atom possessed by R is a hydrogen atom 125A ~R 128A , The substituent R is R 125A ~R 128A a hydrogen atom possessed by A hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in formulae (32D-1) and (32D-2), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 Hydrogen atoms of the substituents At least one of the is a deuterium atom.)

[0250] In one embodiment, at least one of the hydrogen atoms possessed by the compound represented by the formulae (40), (41), (42-1) to (42-3), or (43-1) to (43-3) is a deuterium atom.

[0251] In one embodiment, the compound represented by the formula (41) is a compound represented by the formula (41) having a hydrogen atom (R 101A ~R 108A ) is a deuterium atom.

[0252] In one embodiment, the compound represented by formula (40) is a compound represented by formula (40D):

[0253] [ka]

[0254] (In formula (40D), L 101 and Ar 101 is as defined in the above formula (10). R 101A , and R 103A ~R 108A At least one pair of adjacent two or more of the above does not form a substituted or unsubstituted saturated or unsaturated ring. R 101A , and R 103A ~R 108A are each independently A hydrogen atom, or is a substituent R. The substituent R is as defined in formula (10). However, R is a hydrogen atom. 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 A hydrogen atom possessed by a substituent of At least one of the is a deuterium atom.)

[0255] In one embodiment, R in formula (40D) 101A , and R 103A ~R 108A At least one of the is a deuterium atom.

[0256] In one embodiment, the compound represented by formula (40D) is a compound represented by formula (41D):

[0257] [ka]

[0258] (In formula (41D), L 101 and Ar 101 is as defined in formula (40D) above. However, in formula (41D), A hydrogen atom bonded to a carbon atom constituting an anthracene skeleton, L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 A hydrogen atom held by Ar 101 A hydrogen atom possessed by a substituent of At least one of the is a deuterium atom.)

[0259] In one embodiment, the compound represented by formula (40D) is a compound represented by any one of the following formulae (42D-1) to (42D-3).

[0260] [ka]

[0261] (In formulas (42D-1) to (42D-3), R 101A ~R 108A , L 101 and Ar 101 is as defined in formula (40D) above. However, in the formula (42D-1), R is a hydrogen atom 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of the formula: At least one of the hydrogen atoms bonded to the carbon atoms constituting the phenyl group in the above formula (42D-1) is a deuterium atom. R which is a hydrogen atom in the formula (42D-2) 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of the formula: At least one of the hydrogen atoms bonded to the carbon atoms constituting the naphthyl group in the above formula (42D-2) is a deuterium atom. R which is a hydrogen atom in the formula (42D-3) 101A , and R 103A ~R 108A , The substituent R is R 101A , and R 103A ~R 108A a hydrogen atom possessed by L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of the formula: A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the formula (42D-3) At least one of the is a deuterium atom.)

[0262] In one embodiment, the compounds represented by the formulae (42D-1) to (42D-3) are compounds represented by any of the following formulae (43D-1) to (43D-3).

[0263] [ka]

[0264] (In formulas (43D-1) to (43D-3), L 101 and Ar 101 is as defined in formula (40D) above. provided that a hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the formula (43D-1), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of At least one of the hydrogen atoms bonded to the carbon atoms constituting the phenyl group in the above formula (43D-1) is a deuterium atom. A hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the formula (43D-2), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of At least one of the hydrogen atoms bonded to the carbon atoms constituting the naphthyl group in the above formula (43D-2) is a deuterium atom. A hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the formula (43D-3), L 101 a hydrogen atom possessed by L 101 A hydrogen atom possessed by a substituent of Ar 101 a hydrogen atom possessed by Ar 101 A hydrogen atom carried by a substituent of A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the formula (43D-3) At least one of the is a deuterium atom.)

[0265] Specific examples of the compound represented by formula (10) include the compounds shown below. The compound represented by formula (10) is not limited to these specific examples. In the specific examples below, Me represents a methyl group, and D represents a deuterium atom.

[0266] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0267] As described above, the organic EL device according to one aspect of the present invention has a cathode, an anode, and an emitting layer between the cathode and the anode. The emitting layer contains the compounds represented by formulas (1-1) and (1-3) or the compounds represented by formulas (1-2) and (1-3). However, other than that, conventionally known materials and device configurations can be used as long as they do not impair the effects of the present invention. The content of the compounds represented by formulae (1-1) and (1-3) or the compounds represented by formulae (1-2) and (1-3) in the light-emitting layer is preferably from 1% by mass to 20% by mass based on the entire light-emitting layer.

[0268] Representative element configurations of the organic EL element of the present invention include: (1) Anode / light-emitting layer / cathode (2) Anode / hole injection layer / light emitting layer / cathode (3) Anode / light-emitting layer / electron injection / transport layer / cathode (4) Anode / hole injection layer / light-emitting layer / electron injection / transport layer / cathode (5) Anode / organic semiconductor layer / light-emitting layer / cathode (6) Anode / organic semiconductor layer / electron barrier layer / light-emitting layer / cathode (7) Anode / organic semiconductor layer / light-emitting layer / adhesion improvement layer / cathode (8) Anode / hole injection / transport layer / light-emitting layer / electron injection / transport layer / cathode (9) Anode / insulating layer / light-emitting layer / insulating layer / cathode (10) Anode / inorganic semiconductor layer / insulating layer / light-emitting layer / insulating layer / cathode (11) Anode / organic semiconductor layer / insulating layer / light-emitting layer / insulating layer / cathode (12) Anode / insulating layer / hole injection / transport layer / light-emitting layer / insulating layer / cathode (13) Anode / insulating layer / hole injection / transport layer / light-emitting layer / electron injection / transport layer / cathode The following structures can be mentioned. Among the above, the configuration (8) is preferably used, but the present invention is not limited to this.

[0269] In this specification, the term "hole injection / transport layer" means "at least one of a hole injection layer and a hole transport layer", and the term "electron injection / transport layer" means "at least one of an electron injection layer and an electron transport layer".

[0270] Hereinafter, members that can be used in the organic EL device according to one embodiment of the present invention and materials other than the above-mentioned compounds that constitute each layer will be described.

[0271] (substrate) The substrate is used as a support for the light-emitting element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples of the flexible substrate include plastic substrates made of polycarbonate and polyvinyl chloride.

[0272] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (e.g., titanium nitride), etc.

[0273] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.).

[0274] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, other substances may be used as long as they have a higher hole transport property than electron transport properties. The layer containing the substance with high hole transport properties may be not only a single layer, but also a laminate of two or more layers made of the above substances.

[0275] (Guest (dopant) material in the light-emitting layer) The light-emitting layer is a layer containing a highly light-emitting substance, and in addition to the above-described materials used in the present invention (the compounds represented by formulas (1-1) and (1-3), or the compounds represented by formulas (1-2) and (1-3)), various materials can be used. For example, as the highly light-emitting substance, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state. Examples of blue-based fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Examples of green-based fluorescent materials that can be used in the light-emitting layer include aromatic amine derivatives. Examples of red-based fluorescent materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives. As blue phosphorescent materials usable in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, platinum complexes, etc. are used. As green phosphorescent materials usable in the light-emitting layer, iridium complexes, etc. are used. As red phosphorescent materials usable in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, europium complexes, etc. are used.

[0276] (Host material for the light-emitting layer) The light-emitting layer may have a structure in which the highly light-emitting substance (guest material) described above is dispersed in another substance (host material). As a substance for dispersing the highly light-emitting substance, various substances can be used in addition to the above-described material used in the present invention (compound represented by formula (10)), and it is preferable to use a substance having a lower lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than the highly light-emitting substance. Examples of substances (host materials) for dispersing highly luminescent substances include 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, naphthacene derivatives, fluoranthene derivatives, triphenylene derivatives, fluorene derivatives, and chrysene derivatives; and 4) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives. In addition, a delayed fluorescent (thermally activated delayed fluorescent) compound can be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound.

[0277] (electron transport layer) The electron transport layer is a layer containing a substance with high electron transport properties, and may be formed using 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, or a phenanthroline derivative, or 3) a polymer compound.

[0278] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. The electron injection layer may contain a metal complex compound such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), or 8-hydroxyquinolinolato-lithium (Liq), or a lithium oxide (LiO x) or an alkali metal, alkaline earth metal, or a compound thereof can be used.

[0279] (cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material 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), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0280] In the organic EL element according to one embodiment of the present invention, the method of forming each layer is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. Each layer such as the light-emitting layer can be formed by a known method such as vacuum deposition, molecular beam deposition (MBE), or a coating method such as dipping a solution dissolved in a solvent, spin coating, casting, bar coating, or roll coating.

[0281] In the organic EL device according to one embodiment of the present invention, the thickness of each layer is not particularly limited, but in order to generally suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency, the thickness is usually preferably in the range of several nm to 1 μm.

[0282] [Electronic equipment] An electronic device according to an aspect of the present invention includes the organic EL element according to an aspect of the present invention. Specific examples of electronic devices include display components such as organic EL panel modules, display devices for televisions, mobile phones, and personal computers, and light-emitting devices such as lighting and vehicle lamps. EXAMPLES

[0283] EXAMPLES Hereinafter, examples of the present invention will be described, but the present invention is not limited to these examples.

[0284] <Compound> The compounds represented by formulae (1-1) and (1-3) or the compounds represented by formulae (1-2) and (1-3) used in the examples are shown below. [ka] [ka] [ka]

[0285] The compounds used in the comparative examples are shown below. [ka]

[0286] Other compounds used in the examples and comparative examples are shown below. [ka]

[0287] Example 1 <Fabrication of organic EL elements> A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatic 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 cleaned glass substrate with the transparent electrode was attached to a substrate holder in a vacuum deposition apparatus, and compound HI was deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, forming a compound HI film with a thickness of 5 nm. This HI film functions as a hole injection layer.

[0288] Following the formation of this HI film, a compound HT1 was evaporated to form an HT1 film with a thickness of 80 nm on the HI film, which served as a first hole transport layer. Following the formation of the HT1 film, a compound HT2 was evaporated to form a 10 nm-thick HT2 film on the HT1 film, which served as a second hole transport layer. On the HT2 film, BH-1 (host material) and BD-1 (dopant material) were co-deposited so that the ratio (weight ratio) of compound BD-1 was 2%, to form an emitting layer with a thickness of 25 nm.

[0289] Compound HBL was evaporated onto this light-emitting layer to form an electron transport layer with a thickness of 10 nm. Compound ET, an electron injection material, was evaporated onto this electron transport layer to form an electron injection layer with a thickness of 15 nm. LiF was evaporated onto this electron injection layer to form a LiF film with a thickness of 1 nm. Metal Al was evaporated onto this LiF film to form a metal cathode with a thickness of 80 nm.

[0290] The device configuration of the organic EL device of Example 1 is shown in schematic form as follows. ITO(130) / HI1(5) / HT1(80) / HT2(10) / BH-1:BD-1(25:2%) / HBL(10) / ET(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm).

[0291] <Evaluation of organic EL elements> The resulting organic EL device was subjected to a current density of 50 mA / cm 2 A voltage was applied so that the voltage was 0.01 V, and the time required for the luminance to reach 95% of the initial luminance (LT95) was measured. The results are shown in Table 1. The values ​​in the table are relative values ​​when the LT95 of Comparative Example 1 described below was taken as 100%. The evaluation results are shown in Table 1.

[0292] Examples 2 to 15 and Comparative Example 1 Organic EL devices were produced and evaluated in the same manner as in Example 1, except that the compounds shown in Table 1 were used as the dopant materials in the emitting layer. The results are shown in Table 1.

[0293] [Table 1]

[0294] <Synthesis of Compounds> Compounds BD-1 to 16 and BD-Ref were synthesized according to the following general synthetic route. [ka]

[0295] (1) Synthesis of BD-1 BD-1 was synthesized according to the following synthetic route.

[0296] [ka]

[0297] Intermediate A (9.00 g) and 4-t-butylcyclohexan-1-one (5.38 g) were added to acetic acid (35 mL) and heated at 100° C. for 6 hours with stirring under an argon atmosphere. Dichloromethane and water were added to the reaction solution, and the organic phase was separated and washed with an aqueous solution of sodium bicarbonate. After concentration under reduced pressure, intermediate B-1 was obtained by purifying it by column chromatography (5.94 g, 50% yield).

[0298] [ka]

[0299] Intermediate B-1 (6.32 g) and 2,3-dichloro-5,6-dicyano-p-benzoquinone (8.42 g) were added to toluene (90 mL) and heated at 100° C. for 3 hours with stirring under an argon atmosphere. The reaction solution was filtered through Celite and then purified by column chromatography to obtain intermediate C-1 (5.50 g, 88% yield).

[0300] [ka]

[0301] Intermediate C-1 (5.80 g), bis(pinacolato)diboron (13.12 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.25 g), and potassium acetate (3.38 g) were added to 1,4-dioxane (120 mL) and heated at 100° C. for 4 hours with stirring under an argon atmosphere. The reaction solution was filtered through Celite, and then purified by column chromatography and recrystallization to obtain intermediate D-1 (3.65 g, 55% yield).

[0302] [ka]

[0303] Intermediate D-1 (8.37 g), 1,4-dibromo-2,5-diiodobenzene (4.30 g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.29 g), and potassium carbonate (3.66 g) were added to a mixed solvent of toluene (129 mL) and water (65 mL), and heated at 90°C for 7 hours while stirring under an argon atmosphere. Toluene and water were added to the reaction solution, and the mixture was stirred at room temperature. The organic phase was separated, subjected to column chromatography, and then washed with toluene to obtain intermediate E-1 (4.42 g, yield 67%).

[0304] [ka]

[0305] Intermediate E-1 (5.04 g), copper(I) iodide (0.13 g), 1,10-phenanthroline monohydrate (0.24 g), and potassium carbonate (2.33 g) were added to dimethylformamide (135 mL) and heated at 100° C. for 3 hours with stirring under an argon atmosphere. Water (150 mL) was added to the reaction solution, and the solid was filtered and then purified by column chromatography to obtain intermediate F-1 (3.54 g, 90% yield).

[0306] [ka]

[0307] A toluene solution (1M, 2.8mL) of lithium hexamethyldisilazide (LiHMDS) was added dropwise to a suspension of intermediate F-1 (0.71g), diphenylamine (0.43g), tris(dibenzylideneacetone)dipalladium(0) (0.06g), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (0.23g) in toluene (60mL), and the mixture was heated at 100°C for 3 hours while stirring under an argon atmosphere. After cooling to room temperature, the reaction solution was subjected to column chromatography. The obtained crude product was purified by column chromatography and recrystallization to obtain BD-1 (0.72g, yield 70%). The molecular weight of BD-1 was 851.11, and the mass spectrum analysis result of the obtained compound showed that m / z (mass to charge ratio) = 851, so it was identified as compound BD-1.

[0308] (2) Synthesis of compound BD-2 The compound was synthesized in the same manner as that for compound BD-1, except that 4,4'-dimethyl-diphenylamine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-2 was 907.22, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 907, so it was identified as compound BD-2.

[0309] (3) Synthesis of compound BD-3 The compound was synthesized in the same manner as that for compound BD-1, except that 4,4'-diethyl-diphenylamine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-3 was 963.33, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 963, so it was identified as compound BD-3.

[0310] (4) Synthesis of compound BD-4 The compound was synthesized in the same manner as that for compound BD-1, except that 4-isopropyl-diphenylamine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-4 was 935.27, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 935, so that the compound was identified as compound BD-4.

[0311] (5) Synthesis of compound BD-5 The compound was synthesized in the same manner as that for compound BD-1, except that 3,3'-dimethyl-diphenylamine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-5 was 907.22, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 907, so it was identified as compound BD-5.

[0312] (6) Synthesis of compound BD-6 The compound was synthesized in the same manner as that of compound BD-1, except that 3-t-butyl-diphenylamine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-6 was 963.33, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 963, so it was identified as compound BD-6.

[0313] (7) Synthesis of compound BD-Ref

[0314] [ka]

[0315] Intermediate F-Ref was synthesized in the same manner as in the synthesis of intermediates B-1 to F-1, except that cyclohexanone was used instead of 4-t-butylcyclohexan-1-one as the reaction raw material.

[0316] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate F-Ref was used instead of intermediate F-1 as the reaction raw material. The molecular weight of BD-Ref was 738.89, and the mass spectrum analysis result of the obtained compound showed m / z (mass-to-charge ratio) = 738, so that the compound was identified as compound BD-Ref.

[0317] (8) Synthesis of compound BD-7

[0318] The compound was synthesized in the same manner as that of compound BD-1, except that N-(4-t-butylphenyl)-[1,1'-biphenyl]-2-amine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-7 was 1115.52, and the mass spectrum analysis result of the obtained compound was m / z (mass to charge ratio) = 1115, so it was identified as compound BD-7.

[0319] (9) Synthesis of compound BD-8

[0320] The compound was synthesized in the same manner as that of compound BD-1, except that N-phenyl-[1,1'-biphenyl]-2-amine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-8 was 1003.31, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 1003, so it was identified as compound BD-8.

[0321] (10) Synthesis of compound BD-9

[0322] The compound was synthesized in the same manner as that of compound BD-1, except that 2-(1-naphthalenyl)-diphenylamine was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-9 was 1103.43, and the mass spectrum analysis result of the obtained compound showed m / z (mass-to-charge ratio) = 1103, so it was identified as compound BD-9.

[0323] (11) Synthesis of compound BD-10

[0324] [ka]

[0325] [1,1'-biphenyl]-2-amine (21.4g), 1-bromo-3-t-butylbenzene (27.0g), tris(dibenzylideneacetone)dipalladium(0) (1.74g), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (2.37g), and sodium t-butoxide (17.1g) were added to toluene (253mL) and heated at 100°C for 3 hours with stirring under an argon atmosphere. The reaction solution was filtered through Celite and purified by column chromatography to obtain intermediate G-1 (28.6g, 75% yield).

[0326] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate G-1 was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-10 was 1115.52, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 1115, so it was identified as compound BD-10.

[0327] (12) Synthesis of compound BD-11

[0328] [ka]

[0329] Intermediate G-2 was synthesized in the same manner as in the synthesis of intermediate G-1, except that 4-t-butyl-[1,1'-biphenyl]-2-amine was used instead of [1,1'-biphenyl]-2-amine and bromobenzene was used instead of 1-bromo-3-t-butylbenzene as reaction raw materials.

[0330] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate G-2 was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-11 was 1115.52, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 1115, so it was identified as compound BD-11.

[0331] (13) Synthesis of compound BD-12

[0332] [ka]

[0333] Intermediate G-3 was synthesized in the same manner as in the synthesis of intermediate G-1, except that [1,1'-biphenyl-2',3',4',5',6'-d5]-2-amine was used instead of [1,1'-biphenyl]-2-amine and bromobenzene-d5 was used instead of 1-bromo-3-t-butylbenzene as reaction raw materials.

[0334] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate G-3 was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-12 was 1023.43, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 1023, so it was identified as compound BD-12.

[0335] (14) Synthesis of compound BD-13

[0336] [ka]

[0337] Intermediate G-4 was synthesized in the same manner as in the synthesis of intermediate G-1, except that bromobenzene-d5 was used instead of 1-bromo-3-t-butylbenzene as the reaction raw material.

[0338] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate G-4 was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-13 was 1013.37, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 1013, so it was identified as compound BD-13.

[0339] (15) Synthesis of compound BD-14

[0340] [ka]

[0341] Intermediate G-5 was synthesized in the same manner as in the synthesis of intermediate G-1, except that [1,1'-biphenyl-2',3',4',5',6'-d5]-2-amine was used instead of [1,1'-biphenyl]-2-amine and bromobenzene was used instead of 1-bromo-3-t-butylbenzene as reaction raw materials.

[0342] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate G-5 was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-14 was 1013.37, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 1013, so it was identified as compound BD-14.

[0343] (16) Synthesis of compound BD-15

[0344] [ka]

[0345] Intermediate G-6 was synthesized in the same manner as in the synthesis of intermediate G-1, except that [1,1'-biphenyl-2',3,3',4,4',5,5',6,6'-d9]-2-amine was used instead of [1,1'-biphenyl]-2-amine and bromobenzene-d5 was used instead of 1-bromo-3-t-butylbenzene as reaction raw materials.

[0346] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate G-6 was used instead of diphenylamine as the reaction raw material. The molecular weight of BD-15 was 1031.48, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 1031, so it was identified as compound BD-15.

[0347] (17) Synthesis of compound BD-16

[0348] [ka]

[0349] Intermediate F-2 was synthesized in the same manner as in the synthesis of Intermediates B-1 to F-1, except that 2-t-butylcyclohexan-1-one was used instead of 4-t-butylcyclohexan-1-one as the reaction raw material.

[0350] The compound was synthesized in the same manner as that for compound BD-1, except that intermediate F-2 was used instead of intermediate F-1 as the reaction raw material. The molecular weight of BD-16 was 851.11, and the mass spectrum analysis result of the obtained compound was m / z (mass-to-charge ratio) = 851, so that the compound was identified as compound BD-16.

[0351] Although some embodiments and / or examples of the present invention have been described in detail above, those skilled in the art can easily make many modifications to these exemplary embodiments and / or examples without substantially departing from the novel teachings and advantages of the present invention, and therefore many such modifications are within the scope of the present invention. The contents of all documents cited in this specification and of the application from which this application claims priority under the Paris Convention are incorporated by reference in their entirety.

Claims

1. A compound represented by the following formula (3): 【Chemistry 1】 (In the above formula (3), R 5 and R 14 are each independently -N(R 36 )(R 37 ). Either R 1 or R 3 is an unsubstituted alkyl group having 1 to 50 carbon atoms. Either R 10 or R 12 is an unsubstituted alkyl group having 1 to 50 carbon atoms. R 2 , R 4 , R 6 , R 7 , R 11 , R 13 , and R 15 to R 17 , as well as R 1 , R 3 , R 10 , and R 12 which are not the unsubstituted alkyl group having 1 to 50 carbon atoms, are hydrogen atoms. R 36 and R 37 each independently represent a substituted or unsubstituted aryl group having 6 ring carbon atoms. When there are a plurality of R 36 and R 37, each of the plurality of R 36 and R 37 may be the same or different.

2. R １ , R ３ , R １０ Or R １２ The compound according to claim 1, wherein when R is an alkyl group, all or a part of the hydrogen atoms contained in the alkyl group, and the hydrogen atoms contained in R 36 and R 37 are deuterium atoms.

3. R １ , R ３ , R １０ Or R １２ The compound according to claim 1 or 2, wherein when R is an alkyl group, a hydrogen atom contained in the alkyl group, and a hydrogen atom contained in R 36 and R 37 that is not a deuterium atom, are protium atoms.

4. The compound according to any one of claims 1 to 3, wherein the compound represented by formula (3) is a compound represented by the following formula (9-2): 【Chemistry 2】 (In the above formula (9-2), R ３ , R １２ , and R17 are as defined in formula (3) above. R Ａ , R Ｂ , R Ｃ and R Ｄ are each independently a substituted or unsubstituted phenyl group.

5. The compound according to any one of claims 1 to 3, wherein the compound represented by formula (3) is a compound represented by the following formula (9-3): 【Chemistry 3】 (In the formula (9-3), R １ , R １０ , and R17 are as defined in formula (3) above. R Ａ , R Ｂ , R Ｃ and R Ｄ are each independently a substituted or unsubstituted phenyl group.

6. R Ａ , R Ｂ , R Ｃ and R Ｄ and each independently represent a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms or an unsubstituted phenyl group.

7. In the case of "substituted or unsubstituted", the substituent is an alkyl group having 1 to 50 carbon atoms, a haloalkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, an aralkyl group having 7 to 50 carbon atoms, -Si(R ４１ ) (R ４２ ) (R ４３ ), -C(=O)R ４４ , -COOR ４５ , -S(=O) ２ R ４６ , -P(=O)(R ４７ ) (R ４８ ), -Ge(R ４９ ) (R ５０ ) (R ５１ ), -N(R ５２ ) (R ５３ ) (where R ４１ ~R ５３ are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms. ４１ ~R ５３ When two or more are present, two or more R ４１ ~R ５３ may be the same or different.), a hydroxy group, a halogen atom, a cyano group, a nitro group, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms.

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

9. A cathode; An anode; at least one organic layer disposed between the cathode and the anode; having An organic electroluminescence device, wherein at least one of the at least one organic layer comprises the compound according to any one of claims 1 to 7.

10. 10. The organic electroluminescence device according to claim 9, wherein at least one of the at least one organic layer comprises a second compound which is not identical to the first compound according to any one of claims 1 to 7.

11. 11. The organic electroluminescence device according to claim 10, wherein the second compound is a heterocyclic compound or a condensed aromatic compound.

12. 12. The organic electroluminescence device according to claim 10, wherein the second compound is an anthracene derivative.

13. The organic electroluminescence device according to any one of claims 10 to 12, wherein the second compound is a compound represented by the following formula (10): 【Chemistry 4】 [In formula (10), R １０１ ~R １１０ one or more pairs of adjacent two or more of the above groups form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. The substituted or unsubstituted R １０１ ~R １１０ are each independently Hydrogen atom, a substituent R, or It is a group represented by the following formula (11). -L １０１ -Ar １０１ (11) (In formula (11), L １０１ teeth, Single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms. Ar １０１ teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ )、 -O-(R ９０４ )、 -S-(R ９０５ )、 -N(R ９０６ )(R ９０７ )、 Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more substituents R are present, the two or more substituents R may be the same or different. R ９０１ ~R ９０７ are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R ９０１ ~R ９０７ When there are two or more R ９０１ ~R ９０７ may be the same or different. However, R does not form a substituted or unsubstituted saturated or unsaturated ring. １０１ ~R １１０ At least one of the formulas (11) is a group represented by the formula (11). When two or more formulas (11) are present, the two or more groups represented by the formulas (11) may be the same or different.

14. Ar １０１ 14. The organic electroluminescence device according to claim 13, wherein at least one of the above is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

15. 15. The organic electroluminescence device according to claim 9, wherein at least one of the at least one organic layer is a light-emitting layer.

16. 16. The organic electroluminescence device according to claim 15, further comprising a hole transport layer between the anode and the light emitting layer.

17. 17. The organic electroluminescence device according to claim 15, further comprising an electron transport layer between the cathode and the light emitting layer.

18. The organic electroluminescence device according to any one of claims 15 to 17, wherein the light-emitting layer contains a compound represented by the formula (10).

19. The organic electroluminescence device according to any one of claims 15 to 18, wherein the light-emitting layer further comprises a delayed fluorescent host compound.

20. An electronic device comprising the organic electroluminescence element according to any one of claims 9 to 19.

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