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

Abstract

To provide a compound that can achieve an organic EL device with increased performance.SOLUTION: For example, the following compound ET-3 is illustrated.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter also 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. Conventional organic EL elements have not yet achieved sufficient performance. Although the materials used in organic EL elements have been gradually improved to enhance their performance, further improvements are still required. Patent Document 1 discloses the use of a compound having a specific structure in the organic layer of an organic EL device. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2019 / 098796 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a compound capable of realizing an organic EL device with higher performance. [Means for solving the problem]

[0005] Means for Solving the Problems The present inventors have conducted extensive research in order to achieve the above object, and as a result have found that use of a compound having a specific structure results in an organic EL device with higher performance, thereby completing the present invention. According to the present invention, the following compounds and the like are provided: 1. A compound represented by the following formula (1): [ka] [In formula (1), Ar1 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. L1 and L2 each independently represent a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. R1 to R4 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. At least one pair of adjacent two or more of R1 to R4 are not bonded to each other. R 11 ~R 17 Among adjacent pairs of R, one or more pairs of R which are bonded to each other form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring. 11 ~R 17 are each independently a hydrogen atom or a substituent R. R 21 and R 22 R may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. 23 ~R 26 Among adjacent pairs of R, one or more pairs of R 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. 27 and R 28 R may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. 22 and R 23 do not bond to each other. R 26 and R 27 are not bonded to each other. R which does not form a substituted or unsubstituted saturated or unsaturated ring 21 ~R 28 are each independently a hydrogen atom or a substituent R. 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 ) (where R 901 ~R 907 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or R is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms is selected from the group consisting of: When two or more substituents R are present, the two or more substituents R may be the same or different. Effect of the Invention

[0006] According to the present invention, it is possible to provide a compound that can realize an organic EL device with higher performance. [Brief description of the drawings]

[0007] [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

[0008] [Definition] In this specification, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

[0009] 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.

[0010] 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.

[0011] 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.

[0012] 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.

[0013] 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.

[0014] 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.

[0015] "Substituents Described Herein" The substituents described in this specification will be described below.

[0016] 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.

[0017] "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.

[0018] 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).

[0019] [ka]

[0020] [ka]

[0021] 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.

[0022] "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.

[0023] 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).

[0024] 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).

[0025] 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, 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.

[0026] 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.

[0027] 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).

[0028] 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):

[0029] [ka]

[0030] [ka]

[0031] 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.

[0032] 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.

[0033] 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].

[0034] 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].

[0035] 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):

[0036] 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.

[0037] "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.

[0038] 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.

[0039] Substituted alkyl groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0040] "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.

[0041] Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, 2-butenyl group, and 3-Butenyl group.

[0042] 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.

[0043] "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.

[0044] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group

[0045] "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.

[0046] 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.

[0047] Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl group.

[0048] -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.

[0049] -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.

[0050] -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.

[0051] -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.

[0052] "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.

[0053] "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.

[0054] "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.

[0055] "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.

[0056] "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.

[0057] "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.

[0058] "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.

[0059] "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.

[0060] "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.

[0061] 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.

[0062] 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.

[0063] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in the specification.

[0064] [ka]

[0065] In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise specified in the specification.

[0066] [ka]

[0067] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a binding site.

[0068] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0069] [ka]

[0070] In the above general formulae (TEMP-34) to (TEMP-41), * represents a binding site.

[0071] 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.

[0072] "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.

[0073] "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.

[0074] "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.

[0075] 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.

[0076] [ka]

[0077] [ka]

[0078] 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 binding site.

[0079] [ka]

[0080] 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 binding site.

[0081] [ka]

[0082] 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 binding site.

[0083] 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.

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

[0093] The above is an explanation of "the substituents described in this specification".

[0094] - "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.

[0095] [ka]

[0096] 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 .

[0097] 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).

[0098] [ka]

[0099] When a "set of two or more adjacent units" forms a ring, it 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.

[0100] [ka]

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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").

[0105] 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.

[0106] 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:

[0107] 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:

[0108] 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."

[0109] 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.

[0110] 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.

[0111] [New compounds] The compound according to one aspect of the present invention is represented by the following formula (1). [ka] [In formula (1), Ar1 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. L1 and L2 each independently represent a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. R1 to R4 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. At least one pair of adjacent two or more of R1 to R4 are not bonded to each other. R 11 ~R 17Among adjacent pairs of R, one or more pairs of R which are bonded to each other form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring. 11 ~R 17 are each independently a hydrogen atom or a substituent R. R 21 and R 22 R may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. 23 ~R 26 Among adjacent pairs of R, one or more pairs of R 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. 27 and R 28 R may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. 22 and R 23 do not bond to each other. R 26 and R 27 are not bonded to each other. R which does not form a substituted or unsubstituted saturated or unsaturated ring 21 ~R 28 are each independently a hydrogen atom or a substituent R. 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 ) (where R 901 ~R 907 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or R is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and Substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms is selected from the group consisting of: When two or more substituents R are present, the two or more substituents R may be the same or different.

[0112] The compound according to one embodiment of the present invention has the above structure, and when used in an organic EL device, the compound can improve the performance of the device. As one specific effect, an organic EL device having a long life can be realized. As shown in formula (1), the compound according to one embodiment of the present invention includes a structure in which a 4-dibenzothiophenyl group is directly bonded to a triazine ring. The triazine ring has a larger absolute value of affinity (deeper affinity) than, for example, a pyrimidine ring, which is the same nitrogen-containing 6-membered ring, and the dibenzothiophenyl group bonded at the 4th (or 5th) position among the 1st to 8th positions has the largest absolute value of affinity. Therefore, the compound according to one embodiment of the present invention has excellent electron injection properties from the cathode and is considered to contribute to improving the performance of an organic EL device. In addition, by forming a structure in which an ortho-phenylene group (a phenylene group to which R1 to R4 are bonded) is directly bonded to the triazine ring, it is possible to control the electron mobility and extend the life of an organic EL device.

[0113] In one embodiment, Ar1 is a group represented by formula (1A): [ka] (In formula (1A), R 1A ~R 10A Any one of these represents a bond to L1 in the above formula (1). R does not represent a bond with L1 1A ~R 10A two or more adjacent ones of these may be bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. R does not represent a bond with L1 and does not form the substituted or unsubstituted saturated or unsaturated ring. 1A ~R 10A are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0114] R 1A ~R 10A represents a bond with L1 in the formula (1). 1A ~R 10A When L1 is a single bond, it means that the carbon atom on the triazine ring to which L1 is bonded and the carbon atom on the triazine ring to which R 1A ~R 10A is directly bonded to one of the carbon atoms on the benzene ring to which is bonded via a single bond.

[0115] In one embodiment, R in formula (1A) 1A represents a bond with L1. In one embodiment, R in formula (1A) 5A and R 6A are bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring. In one embodiment, R does not represent a bond with L and does not form the substituted or unsubstituted saturated or unsaturated ring. 1A ~R 10A each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0116] In one embodiment, L1 is a single bond.

[0117] In one embodiment, the compound represented by formula (1) is a compound represented by the following formula (1-1). [ka] (In formula (1-1), L2, R1~R4, R 11 ~R 17 , and R 21 ~R 28 is as defined in formula (1) above. R 31 ~R 39 one or more of a set of two or more adjacent groups among these are bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. The substituted or unsubstituted R which does not form a saturated or unsaturated ring 31 ~R 39 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0118] In one embodiment, R in formula (1-1) 34 and R 35 are bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring. In one embodiment, the substituted or unsubstituted R 31 ~R 39each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0119] In one embodiment, R1 to R4 are hydrogen atoms.

[0120] In one embodiment, R 11 ~R 17 Any pair of two or more adjacent groups of R 31 ~R 39 Any pair of two or more adjacent groups of R 21 ~R 28 Any pair of two or more adjacent groups will not bond to each other.

[0121] In one embodiment, R 11 ~R 17 Any pair of two or more adjacent groups of R 11 ~R 17 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. In one embodiment, R 11 ~R 17 Any pair of two or more adjacent groups of R 11 ~R 17 is a hydrogen atom.

[0122] In one embodiment, the compound represented by formula (1-1) is a compound represented by formula (1-11): [ka] (In formula (1-11), L2 and R 21 ~R 28 is as defined in the above formula (1-1).

[0123] In one embodiment, the compound represented by formula (1-1) is a compound represented by formula (1-12): [ka] (In formula (1-12), L2 and R 21 ~R 28 is as defined in the above formula (1-1). 41 and R 42 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0124] In one embodiment, R 41 and R 42 each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms;

[0125] In one embodiment, R 21 ~R 28 Among the groups, one or more of adjacent groups are not bonded to each other.

[0126] In one embodiment, R 21 ~R 28 Any pair of two or more adjacent groups of R 21 ~R 28 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. In one embodiment, R 21 ~R 28 Any pair of two or more adjacent groups of R 21 ~R 28 is a hydrogen atom.

[0127] In one embodiment, L2 is a single bond. In one embodiment, L2 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.

[0128] In one embodiment, R 11 ~R 17 Any pair of two or more adjacent groups of R 21 ~R 28Any pair of two or more adjacent groups will not bond to each other.

[0129] As described in the definitions, the term "hydrogen atom" as used herein includes protium, deuterium, and tritium atoms. Thus, the compounds of the invention may contain naturally occurring deuterium atoms. In addition, deuterium atoms may be intentionally introduced into the compound of the invention by using a compound in which some or all of the raw materials are deuterated. Thus, in one embodiment of the present invention, the compound represented by formula (1) contains at least one deuterium atom. That is, the compound of this embodiment may be a compound represented by formula (1) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0130] In the compound represented by formula (1), a hydrogen atom possessed by Ar1; a hydrogen atom possessed by L1; a hydrogen atom when R1 to R4 are hydrogen atoms; R 11 ~R 17 is a hydrogen atom; a hydrogen atom held by L2; and R 21 ~R 28 is a hydrogen atom, at least one hydrogen atom selected from the hydrogen atoms may be a deuterium atom.

[0131] The deuteration rate of a compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a certain deuteration rate is used, a certain proportion of naturally occurring light hydrogen isotopes may be contained. Therefore, the deuteration rate includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio that can be calculated by simply counting the number of deuterium atoms represented by the chemical formula. In one embodiment, the deuteration rate of the compound is, for example, 1% or more, 3% or more, 5% or more, 10% or more, or 50% or more.

[0132] In one embodiment, the substituents in the term "substituted or unsubstituted" and the substituent R are an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and Heterocyclic groups with 5 to 50 ring atoms is a group selected from the group consisting of In one embodiment, the substituents in the term "substituted or unsubstituted" and the substituent R are an alkyl group having 1 to 18 carbon atoms; An aryl group having 6 to 18 ring carbon atoms, and Heterocyclic groups with 5 to 18 ring atoms is a group selected from the group consisting of:

[0133] Specific examples of the compound represented by formula (1) are given below, however, these are merely illustrative and the compound represented by formula (1) is not limited to the following specific examples.

[0134] [ka] [ka] [ka]

[0135] [Materials for organic electroluminescence devices] The compound according to one embodiment of the present invention is useful as a material for an organic EL device, for example, as a material used in the electron transport region of an organic EL device.

[0136] [Organic EL element] An organic EL element according to one embodiment of the present invention will be described. An organic EL device according to one embodiment of the present invention has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers contains a compound according to one embodiment of the present invention.

[0137] The organic EL device according to one embodiment of the present invention preferably includes an anode, an emitting layer, an electron-transporting region, and a cathode in this order, and the electron-transporting region includes the compound according to one embodiment of the present invention.

[0138] Representative examples of the organic EL element include a structure in which the following structures (1) to (4) are laminated on a substrate. (1) Anode / light-emitting layer / cathode (2) Anode / hole transport region / light emitting layer / cathode (3) Anode / Emitting layer / Electron transport region / Cathode (4) anode / hole transport region / light emitting layer / electron transport region / cathode (The " / " indicates that each layer is stacked adjacently.)

[0139] The electron transporting region is usually composed of one or more layers selected from an electron injection layer and an electron transporting layer, and the hole transporting region is usually composed of one or more layers selected from a hole injection layer and a hole transporting layer.

[0140] 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 emitting layer 5, a cathode 10, a hole transporting zone 4 between the anode 3 and the emitting layer 5, and an electron transporting zone 6 between the emitting layer 5 and the cathode 10.

[0141] 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.

[0142] (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.

[0143] (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, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (e.g., titanium nitride).

[0144] (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.).

[0145] (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.

[0146] (Guest (dopant) material in the light-emitting layer) The light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used. For example, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as a highly light-emitting substance. 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.

[0147] (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, 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. As a substance (host material) for dispersing a highly luminescent substance, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; or 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative.

[0148] (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.

[0149] In one embodiment, the electron transport layer may or may not contain other substances as described above in addition to the compound represented by formula (1) above. In one embodiment, the electron transport layer contains, in addition to the compound represented by formula (1), one or more compounds selected from the group consisting of compounds containing an alkali metal and compounds containing a metal belonging to group 13 in the periodic table. Examples of such compounds include lithium fluoride, lithium oxide, 8-hydroxyquinolinolato-lithium (Liq), cesium fluoride, tris(8-quinolinolato)aluminum (Alq3), tris(4-methyl-8-quinolinolato)aluminum (Almq3), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (BAlq), and the like. The content ratio (mass ratio) of the compound represented by formula (1), the compound containing an alkali metal, and the compound containing a metal belonging to Group 13 in the periodic table is not particularly limited, and is, for example, 10:90 to 90:10.

[0150] In an organic EL device according to one embodiment of the present invention, the electron transport zone has, from the light emitting layer side, a first layer (also referred to as a "first electron transport layer" or a "hole blocking layer") and a second layer (also referred to as a "second electron transport layer") in this order, and the second layer contains a compound represented by formula (1). The first layer can have the same structure as the electron transport layer described above.

[0151] (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.

[0152] (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. The cathode is usually formed by a vacuum deposition method or a sputtering method. When a silver paste or the like is used, a coating method or an inkjet method can be used.

[0153] In addition, when an electron injection layer is provided, the cathode can be formed using various conductive materials, such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function.

[0154] In the organic EL element 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.

[0155] 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.

[0156] [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

[0157] <Compound> The compounds represented by formula (1) used in the production of the organic EL devices of Examples 1 to 8 are shown below. [ka]

[0158] The structures of the compounds used in the production of the organic EL devices of Comparative Examples 1 and 2 are shown below. [ka]

[0159] The structures of other compounds used in the production of the organic EL devices of Examples 1 to 8 and Comparative Examples 1 and 2 are shown below. [ka]

[0160] Example 1 <Fabrication of organic EL elements> The organic EL device was fabricated as follows. 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. Compounds HT-1 and HI-1 were co-deposited onto the surface on which the transparent electrode was formed so as to cover the transparent electrode, so that the ratio of compound HI-1 was 3% by mass, thereby forming a first hole transport layer with a thickness of 10 nm. On the first hole transport layer, the compound HT-1 was evaporated to form a second hole transport layer having a thickness of 80 nm. On the second hole transport layer, the compound EBL-1 was evaporated to form a third hole transport layer having a thickness of 5 nm. On the third hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited so that the ratio of compound BD-1 was 4 mass % to form an emitting layer with a thickness of 25 nm. On the light-emitting layer, compound HBL-1 was deposited by vapor deposition to form a first electron transport layer having a thickness of 5 nm. On the first electron transport layer, the compound ET-1 and 8-hydroxyquinolinolato-lithium (Liq) were co-deposited so that the proportion of Liq was 50 mass % to form a second electron transport layer with a thickness of 20 nm. Metal Yb was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm. Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 50 nm.

[0161] The device configuration of the organic EL device of Example 1 is shown in schematic form as follows. ITO(130) / HT-1:HI-1(10:3%) / HT-1(80) / EBL-1(5) / BH-1:BD-1(25:4%) / HBL-1(5) / ET-1:Liq(20:50%) / Yb(1) / Al(50) The numbers in parentheses indicate the film thickness (unit: nm), and the percentages in parentheses indicate the proportion (mass %) of the latter compound in the layer.

[0162] <Evaluation of organic EL elements> The obtained organic EL device was subjected to a current density test at room temperature of 50 mA / cm 2 A voltage was applied to the organic EL element so as to obtain a voltage of 95% relative to the initial brightness, and the time required for the brightness to reach 95% (LT95 (unit: h)) was measured.

[0163] Examples 2 to 4 An organic EL device was prepared and evaluated in the same manner as in Example 1, except that the compound ET-1 was replaced with a compound shown in Table 1. The results are shown in Table 1.

[0164] Comparative Example 1 An organic EL device was prepared and evaluated in the same manner as in Example 1, except that the compound ET-1 was replaced with a compound shown in Table 1. The results are shown in Table 1.

[0165] [Table 1]

[0166] Example 5 <Fabrication of organic EL elements> The organic EL device was fabricated as follows. 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. Compounds HT-2 and HI-1 were co-deposited onto the surface on which the transparent electrode was formed so as to cover the transparent electrode, with the proportion of compound HI-1 being 3% by mass, to form a first hole transport layer with a thickness of 10 nm. On the first hole transport layer, the compound HT-2 was evaporated to form a second hole transport layer having a thickness of 80 nm. On the second hole transport layer, the compound EBL-1 was evaporated to form a third hole transport layer having a thickness of 5 nm. On the third hole transport layer, compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited so that the ratio of compound BD-1 was 4 mass % to form an emitting layer with a thickness of 25 nm. On the light-emitting layer, the compound HBL-1 was evaporated to form a first electron transport layer having a thickness of 5 nm. On the first electron transport layer, the compound ET-1 and Liq were co-deposited such that the proportion of Liq was 50 mass %, to form a second electron transport layer with a thickness of 20 nm. Metal Yb was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm. Metallic Al was evaporated onto the electron injection layer to form a cathode having a thickness of 50 nm.

[0167] The device configuration of the organic EL device of Example 5 is shown in schematic form as follows. ITO(130) / HT-2:HI-1(10:3%) / HT-2(80) / EBL-1(5) / BH-2:BD-1(25:4%) / HBL-1(5) / ET-1:Liq(20:50%) / Yb(1) / Al(50) The numbers in parentheses indicate the film thickness (unit: nm), and the percentages in parentheses indicate the proportion (mass %) of the latter compound in the layer.

[0168] <Evaluation of organic EL elements> The obtained organic EL device was evaluated in the same manner as in Example 1.

[0169] Examples 6 to 8 An organic EL device was prepared and evaluated in the same manner as in Example 5, except that the compound ET-1 was replaced with a compound shown in Table 2. The results are shown in Table 2.

[0170] Comparative Example 2 An organic EL device was prepared and evaluated in the same manner as in Example 5, except that the compound ET-1 was replaced with a compound shown in Table 2. The results are shown in Table 2.

[0171] [Table 2]

[0172] <Synthesis of Compounds> (Synthesis Example 1) Synthesis of ET-1 Compound ET-1 was synthesized according to the following synthetic route. [ka] Intermediate A (3.0 g) synthesized according to the method described in WO 2020-116615 and intermediate B (2.9 g) synthesized according to the method described in WO 2019-189033 were added to 1,2-dimethoxyethane (DME) (130 mL), and argon gas was passed through the solution for 5 minutes. PdCl2(Amphos)2 (0.19 g) and aqueous sodium carbonate solution (2 M, 8.3 mL) were added to this, and the mixture was heated at 80 ° C for 6 hours while stirring under an argon atmosphere. The reaction solution was distilled, and the resulting solid was purified by silica gel column chromatography (developing solvent: hexane / toluene) to obtain ET-1 as a white solid (3.6 g, yield 82%). Mass spectrometry revealed that the molecular weight was 656.81 and m / e was 656, indicating that this was the target compound.

[0173] (Synthesis Example 2) Synthesis of ET-2 (2-1) Synthesis of intermediate C [ka] Using intermediate A (5.0 g) and 2-fluorophenylboronic acid (1.7 g), intermediate C was obtained as a white solid (5.2 g, yield 89%) under the same conditions as those described in Synthesis Example 1.

[0174] (2-2) Synthesis of ET-2 [ka] Intermediate C (5.2 g), 3.6-diphenylcarbazole (3.9 g), and cesium carbonate (10.0 g) were added to N-methylpyrrolidone (NMP) (60 mL) and heated at 150°C for 24 hours while stirring under an argon atmosphere. Methanol and water were added, and the precipitated solid was dissolved in toluene and then passed through silica gel. The distillate was concentrated, and the resulting solid was suspended and washed in ethanol, and further purified by repeated recrystallization from toluene to obtain ET-2 as a white solid (6.5 g, 78% yield). Mass spectrum analysis showed that the m / e was 809 for a molecular weight of 809.00, and the product was identified as the target substance.

[0175] (Synthesis Example 3) Synthesis of ET-3 [ka] Using intermediate D (3.0 g) and intermediate B (2.1 g) synthesized according to the method described in International Publication No. 2021-033724, ET-3 was obtained as a white solid (3.4 g, yield 85%) under the same conditions as those described in (1-2) of Synthesis Example 1. Mass spectrometry revealed that the m / e was 821 for a molecular weight of 821.01, and the product was identified as the target substance.

[0176] (Synthesis Example 4) Synthesis of ET-4 (4-1) Synthesis of intermediate E [ka] Using intermediate A (5.0 g) and 2-chlorophenylboronic acid (1.9 g), intermediate E was obtained as a white solid (5.0 g, yield 86%) under the same conditions as those described in Synthesis Example 1.

[0177] (4-2) Synthesis of ET-4 [ka] Using intermediate E (5.0 g) and 4-(N-carbazolyl)phenylboronic acid (2.6 g), ET-4 was obtained as a white solid (5.3 g, 80% yield) under the same conditions as described in Synthesis Example 1 (1-2). Mass spectrum analysis showed that the molecular weight was 732.91 and m / e was 732, indicating that this was the target compound.

Claims

1. A compound represented by the following formula (1): 【Chemistry 40】 [In formula (1), Ar １ is a group represented by the following formula (1A). 【Chemistry 41】 (In formula (1A), Any one of R 1A to R 10A represents a bond to L 1 in the formula (1). Adjacent two or more of R 1A to R 10A that are not bonded to L 1 are 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. R 1A to R 10A which do not represent a bond with L 1 and do not form the substituted or unsubstituted saturated or unsaturated ring are each independently a hydrogen atom or a substituent R. L １ and L ２ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms. R １ ~R ４ R is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. １ ~R ４ Among the groups, one or more of adjacent groups are not bonded to each other. R １１ ~R １７ Among adjacent pairs of R, one or more pairs of R that are bonded to each other form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring. １１ ~R １７ are each independently a hydrogen atom or a substituent R. R ２１ and R ２２ R are bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. ２３ ~R ２６ Among adjacent groups, one or more groups of R are 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. ２７ and R ２８ R are bonded to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or not to form a substituted or unsubstituted, saturated or unsaturated ring. ２２ and R ２３ do not bond to each other. ２６ and R ２７ are not bonded to each other. ２１ ~R ２８ are each independently a hydrogen atom or a substituent R. 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 ) (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 R is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７ When there are two or more R ９０１ ~R ９０７ may be the same or different.) Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. is selected from the group consisting of: When two or more substituents R are present, the two or more substituents R may be the same or different.

2. In the formula (1A), R １Ａ L １ The compound of claim 1 , wherein

3. L １ The compound according to claim 1 or 2, wherein is a single bond.

4. The compound according to any one of claims 1 to 3, wherein the compound represented by formula (1) is a compound represented by the following formula (1-1): 【Chemistry 42】 (In formula (1-1), L ２ , R １ ~R ４ , R １１ ~R １７ , and R ２１ ~R ２８ is as defined in formula (1) above. R ３１ ~R ３９ one or more of a set of two or more adjacent groups among The substituted or unsubstituted R ３１ ~R ３９ are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

5. R １ ~R ４ The compound according to any one of claims 1 to 4, wherein is a hydrogen atom.

6. R １１ ~R １７ Among R, adjacent pairs of two or more are not bonded to each other, ３１ ~R ３９ adjacent pairs of two or more of R ２１ ~R ２８ The compound according to any one of claims 1 to 5, wherein adjacent pairs of two or more of:

7. R １１ ~R １７ Among R, adjacent pairs of two or more are not bonded to each other, １１ ~R １７ The compound according to any one of claims 1 to 6, wherein is a hydrogen atom.

8. The compound according to any one of claims 4 to 7, wherein the compound represented by formula (1-1) is a compound represented by the following formula (1-11): 【Chemistry 43】 (In formula (1-11), L ２ and R ２１ ~R ２８ is as defined in the above formula (1-1).

9. The compound according to any one of claims 4 to 7, wherein the compound represented by formula (1-1) is a compound represented by the following formula (1-12): 【Chemistry 44】 (In formula (1-12), L ２ and R ２１ ~R ２８ is as defined in the above formula (1-1). ４１ and R ４２ are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

10. R ４１ and R ４２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

11. R ２１ ~R ２８ The compound according to any one of claims 1 to 10, wherein one or more pairs of adjacent two or more of

12. R ２１ ~R ２８ Among R, adjacent pairs of two or more are not bonded to each other, ２１ ~R ２８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

13. R ２１ ~R ２８ Among R, adjacent pairs of two or more are not bonded to each other, ２１ ~R ２８ The compound according to any one of claims 1 to 12, wherein is a hydrogen atom.

14. L ２ The compound according to any one of claims 1 to 13, wherein is a single bond.

15. L ２ The compound according to any one of claims 1 to 13, wherein is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms.

16. R １１ ~R １７ Among R, adjacent pairs of two or more are not bonded to each other, ２１ ~R ２８ The compound according to any one of claims 1 to 15, wherein adjacent pairs of two or more of:

17. The compound according to any one of claims 1 to 16, wherein the compound represented by formula (1) contains at least one deuterium atom.

18. The substituents in the case of "substituted or unsubstituted" and the substituent R are an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and Heterocyclic group having 5 to 50 ring atoms The compound according to any one of claims 1 to 17, wherein the group is selected from the group consisting of:

19. The substituents in the case of "substituted or unsubstituted" and the substituent R are an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and Heterocyclic group having 5 to 18 ring atoms The compound according to any one of claims 1 to 18, wherein the group is selected from the group consisting of:

20. The compound according to any one of claims 1 to 19, which is a material for an organic electroluminescence device.

21. A cathode; An anode; one or more organic layers disposed between the cathode and the anode; having An organic electroluminescence device, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 20.

22. comprising, in order, an anode, an emissive layer, an electron transporting zone, and a cathode; 22. The organic electroluminescent device of claim 21, wherein the electron transporting zone comprises the compound.

23. the electron transport region has a first layer and a second layer in this order from the light emitting layer side, The organic electroluminescent device according to claim 22 , wherein the second layer comprises the compound.

24. The second layer comprises: The compound, one or more compounds selected from the group consisting of compounds containing an alkali metal and compounds containing a metal belonging to Group 13 of the periodic table; The organic electroluminescence device according to claim 23 .

25. An electronic device comprising the organic electroluminescence device according to any one of claims 21 to 24.

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