Compound, organic electroluminescent element, and electronic device

Abstract

To provide an organic EL element with higher performance. A compound represented by formula (1). TIFF0007777714000313.tif33170

Description

[Technical Field]

[0001] The present invention relates to a novel compound, an organic electroluminescence element, 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. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] Conventional organic EL elements have not yet achieved sufficient performance. Although improvements to organic EL elements have been made gradually to enhance their performance, further improvements are still required. Patent Documents 1 to 4 disclose compounds having specific structures that are used in organic EL devices. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent Publication No. 2021-090050 [Patent Document 2] International Publication No. 2023 / 127843 [Patent Document 3] International Publication No. 2023 / 238896 [Patent Document 4] International Publication No. 2009 / 069602 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide an organic EL device with higher performance. [Means for solving the problem]

[0006] As a result of extensive research to achieve the above object, the present inventors have discovered that a high-performance organic EL element can be obtained by using a compound having a specific structure in at least one of the organic layers of the organic EL element, and have completed the present invention.

[0007] According to the present invention, the following compounds and the like are provided: 1. A compound represented by formula (1). [ka] (In formula (1), Ar1 is a substituted or unsubstituted aryl group having four or more fused monocyclic rings. Ar2 is A monovalent group represented by the following formula (21): A monovalent group represented by the following formula (22): It is a substituted or unsubstituted monovalent heterocyclic group having 9 to 50 ring atoms. [ka] In equation (21), R 201 ~R 210 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. When the substituted or unsubstituted monocyclic ring is formed, one of the atoms forming the monocyclic ring is bonded to the benzene ring skeleton of formula (1), or R 201 ~R 210 One of these represents a single bond to the benzene ring skeleton of formula (1). When the substituted or unsubstituted fused ring is formed, one of the atoms forming the fused ring is bonded to the benzene ring skeleton of formula (1), or R 201 ~R 210 One of these represents a single bond to the benzene ring skeleton of formula (1). When the single ring and the fused ring are not formed, R 201 ~R 210 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not form the single ring or the fused ring and does not represent the single bond 201 ~R 210 are each independently a hydrogen atom or a substituent R. In equation (22), R 211 ~R 222 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. When the substituted or unsubstituted monocyclic ring is formed, one of the atoms forming the monocyclic ring is bonded to the benzene ring skeleton of formula (1), or R 211 ~R 222 One of these represents a single bond to the benzene ring skeleton of formula (1). When the substituted or unsubstituted fused ring is formed, one of the atoms forming the fused ring is bonded to the benzene ring skeleton of formula (1), or R 211 ~R 222 One of these represents a single bond to the benzene ring skeleton of formula (1). When the single ring and the fused ring are not formed, R 211 ~R 222 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not form the single ring or the fused ring and does not represent the single bond 211 ~R 222 are each independently a hydrogen atom or a substituent R. One or more pairs of adjacent two or more of R1 to R4 are joined together to form a substituted or unsubstituted monocyclic ring, or Do not bond with each other. The R1 to R4 that do not form a single ring each independently represent: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different. 2. A compound represented by formula (3). [ka] [In formula (3), R 301 ~R 312 At least one of the above is a group represented by the following formula (31). R that is not a group represented by the formula (31) 301 ~R 312 are each independently a hydrogen atom or a substituent R. However, R 307 is a group represented by the formula (31), R 301 ~R 312 are each independently a hydrogen atom or a substituent Q. R 301 ~R 312 One or more pairs of adjacent pairs of the above are not bonded to each other. [ka] (In equation (31), L 301 teeth, single bond, a substituted or unsubstituted phenylene group, or It is a substituted or unsubstituted naphthalenediyl group. n301 is an integer of 0 to 3. If n301 is 0, then (L 301 ) n301 is a single bond. If n301 is 2 or more, L is 2 or more 301 are connected in series. When n301 is 2 or more, L 301 may be the same as or different from each other. Ar 301 represents an unsubstituted aryl group having 6 to 15 ring carbon atoms. n302 is an integer of 1 to 3. If n302 is 2 or more, then 2 or more Ar 301 may be the same as or different from each other. X301 is C(R 329 )(R 330 ), N(R 331 ), O, or S. R 321 ~R 331 One of them is L 301 represents a single bond that connects to R does not represent a single bond 321 ~R 328 Of these, n302 are Ar 301 represents a single bond that connects to R does not represent a single bond 321 ~R 331 are each independently a hydrogen atom or a substituent R. R 329 and R 330 pairs are disjoint.) The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different. The substituent Q 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 ), a halogen atom, a cyano group, a nitro group, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 is as defined for the substituent R. When two or more substituents Q are present, the two or more substituents Q may be the same or different.] 3. A compound represented by formula (4). [ka] [In formula (4), R 401 ~R 412 At least one of the above is a group represented by the following formula (41). R that is not a group represented by the formula (41) 401 ~R 412 are each independently a hydrogen atom or a substituent R. R 401 ~R 412 One or more pairs of adjacent pairs of the above are not bonded to each other. [ka] (In equation (41), L 401 teeth, single bond, a substituted or unsubstituted phenylene group, or It is a substituted or unsubstituted naphthalenediyl group. n401 is an integer of 0 to 3. If n401 is 0, then (L 401 ) n401 is a single bond. If n401 is 2 or more, L is 2 or more. 401 are connected in series. When n401 is 2 or more, L 401 may be the same as or different from each other. Ar 401 represents an unsubstituted aryl group having 6 to 15 ring carbon atoms. n402 is an integer of 1 to 3. If n402 is 2 or more, then 2 or more Ar 401 may be the same as or different from each other. X 401 is C(R 429 )(R 430 ), N(R 431 ), O, or S. R 421 ~R 431 One of them is L 401 represents a single bond that connects to R does not represent a single bond 421 ~R 428 Of these, n402 are Ar 401 represents a single bond that connects to R does not represent a single bond 421 ~R 431are each independently a hydrogen atom or a substituent R. R 429 and R 430 pairs are disjoint.) The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different. However, R is a hydrogen atom. 401 ~R412 , R is the substituent R 401 ~R 412 a hydrogen atom possessed by L 401 a hydrogen atom possessed by R is a hydrogen atom 421 ~R 431 , Ar 401 and a hydrogen atom in R is the substituent R 429 ~R 431 The hydrogen atom wherein one or more hydrogen atoms selected from the group consisting of are deuterium atoms. 4. A cathode; an anode; one or more organic layers disposed between the cathode and the anode; and At least one of the organic layers contains the compound described in any one of 1. to 3. Organic electroluminescent element. 5. An electronic device comprising the organic electroluminescence element according to 4. above. [Effects of the Invention]

[0008] According to the present invention, an organic EL device with higher performance can be provided. [Brief explanation of the drawings]

[0009] [Figure 1] 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 INVENTION

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

[0011] In this specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.

[0012] As used herein, the term "number of ring carbon atoms" refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. Furthermore, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0013] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to the pyridine ring are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0014] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0015] In this specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY atoms" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0016] In this specification, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. In this specification, "substituted" in the context of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the context of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0017] "Substituents described herein" The substituents described in this specification will be explained below.

[0018] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. Unless otherwise specified in this specification, the "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. Unless otherwise specified, the "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0019] "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent, and examples of the substituted aryl group in the specific example group G1A below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.

[0020] Unsubstituted aryl groups (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl groups, 9,9'-spirobifluorenyl group, benzofluorenyl groups, dibenzofluorenyl groups, fluoranthenyl group, benzofluoranthenyl group, perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0021] [ka]

[0022] [ka]

[0023] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl groups, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0024] "Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which a hydrogen atom of the "unsubstituted heterocyclic group" in the specific example group G2A below is replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are also included. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent.

[0025] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

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

[0027] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, a triazolyl group, tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, a triazinyl group, Indolyl groups, isoindolyl groups, an indolizinyl group, a quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, a quinazolinyl group, quinoxalinyl group, benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, acridinyl group, phenazinyl group, a carbazolyl group, a benzocarbazolyl group, morpholino group, phenoxazinyl group, a phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0028] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0029] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): thienyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0030] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0031] [ka]

[0032] [ka]

[0033] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

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

[0035] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0036] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0037] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):

[0038] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y Aor more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

[0039] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when simply referring to an "alkyl group," both an "unsubstituted alkyl group" and a "substituted alkyl group" are included. The term "substituted alkyl group" refers to an "unsubstituted alkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Note that the examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent.

[0040] Unsubstituted alkyl groups (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

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

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

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

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

[0045] "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.

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

[0047] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to an "unsubstituted cycloalkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" of specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself have been replaced with a substituent, and a group in the "substituted cycloalkyl group" of specific example group G6B in which a hydrogen atom of a substituent has been further replaced with a substituent.

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

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

[0050] -Si(R 901 )(R 902 )(R 903 ) a group represented by -Si(R) 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) may be the same as or different from each other.

[0051] -O-(R 904 ) a group represented by -O-(R904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0052] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0053] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

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

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

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

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

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

[0059] "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0060] "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0061] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0062] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.

[0063] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.

[0064] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

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

[0066] [ka]

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

[0068] [ka]

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

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

[0071] [ka]

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

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

[0074] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0075] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0076] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group." Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

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

[0078] [ka]

[0079] [ka]

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

[0081] [ka]

[0082] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding site.

[0083] [ka]

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

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

[0086] [ka]

[0087] [ka]

[0088] [ka]

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

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] [ka]

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

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

[0096] - "When bonded to form a ring" In this specification, the phrase "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle, bond with each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle", the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring", and the case where "one or more pairs of adjacent groups do not bond with each other". In this specification, the cases where "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they bond to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be explained as an example.

[0097] [ka]

[0098] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.

[0099] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A At the same time, R 925 and R 926 and are bonded to each other to form ring Q B When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0100] [ka]

[0101] 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 example above, 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 each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.

[0102] [ka]

[0103] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0104] The "unsaturated ring" includes aromatic hydrocarbon rings and aromatic heterocycles, as well as aliphatic hydrocarbon rings having an unsaturated bond in the ring structure, i.e., a double bond and / or a triple bond (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring having no unsaturated bond, or a non-aromatic heterocycle having no unsaturated bond. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed only with a plurality of atoms in the main skeleton, or with a plurality of atoms in the main skeleton and one or more additional atoms. For example, R 921 and R 922 and Q are bonded together to form a ring A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary 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 a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by

[0105] Here, unless otherwise specified in this specification, the "arbitrary atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In the arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary atom other than a carbon atom is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary atoms" constituting the single ring or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0106] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0107] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and Unsubstituted heterocyclic group having 5 to 50 ring atoms and the like, a group selected from the group consisting of where R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R 903 If there are two or more, there are two or more R 903 are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0108] In one embodiment, the substituents in the term "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and Heterocyclic groups with 5 to 50 ring atoms is a group selected from the group consisting of:

[0109] In one embodiment, the substituents in the term "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; an aryl group having 6 to 18 ring carbon atoms, and Heterocyclic groups with 5 to 18 ring atoms is a group selected from the group consisting of:

[0110] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."

[0111] Unless otherwise specified in this specification, any adjacent substituents may be bonded to each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0112] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0113] [First compound] A first compound according to one aspect of the present invention is represented by formula (1). [ka] (In formula (1), Ar1 is a substituted or unsubstituted aryl group having four or more fused monocyclic rings. Ar2 is A monovalent group represented by the following formula (21): A monovalent group represented by the following formula (22): It is a substituted or unsubstituted monovalent heterocyclic group having 9 to 50 ring atoms. [ka] In equation (21), R 201 ~R 210At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. When the substituted or unsubstituted monocyclic ring is formed, one of the atoms forming the monocyclic ring is bonded to the benzene ring skeleton of formula (1), or R 201 ~R 210 One of these represents a single bond to the benzene ring skeleton of formula (1). When the substituted or unsubstituted fused ring is formed, one of the atoms forming the fused ring is bonded to the benzene ring skeleton of formula (1), or R 201 ~R 210 One of these represents a single bond to the benzene ring skeleton of formula (1). When the single ring and the fused ring are not formed, R 201 ~R 210 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not form the single ring or the fused ring and does not represent the single bond 201 ~R 210 are each independently a hydrogen atom or a substituent R. In equation (22), R 211 ~R 222 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. When the substituted or unsubstituted monocyclic ring is formed, one of the atoms forming the monocyclic ring is bonded to the benzene ring skeleton of formula (1), or R 211 ~R 222 One of these represents a single bond to the benzene ring skeleton of formula (1). When the substituted or unsubstituted fused ring is formed, one of the atoms forming the fused ring is bonded to the benzene ring skeleton of formula (1), or R 211 ~R 222 One of these represents a single bond to the benzene ring skeleton of formula (1). When the single ring and the fused ring are not formed, R 211 ~R 222 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not form the single ring or the fused ring and does not represent the single bond 211 ~R 222 are each independently a hydrogen atom or a substituent R. One or more pairs of adjacent two or more of R1 to R4 are joined together to form a substituted or unsubstituted monocyclic ring, or Do not bond with each other. The R1 to R4 that do not form a single ring each independently represent: hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different.

[0114] When the first compound according to one aspect of the present invention is used in an organic layer of an organic EL device, the device performance can be improved. For example, an organic EL device with low CIE-y can be realized while maintaining high performance in terms of driving voltage and external quantum efficiency (or while improving at least one of these performances).

[0115] The driving voltage, external quantum efficiency, and CIE-y of the organic EL device are measured by the methods described in the Examples.

[0116] CIE-y refers to the y component in the CIE 1931 chromaticity coordinates. Widening the color gamut of displays using organic EL elements and the like is important for expanding the range of colors that can be displayed and for expressing more natural and vivid colors. To achieve a wider color gamut of a display, improving chromaticity is essential. For blue light emission, reducing CIE-y is one indicator for improving chromaticity. The present inventors discovered that a display exhibiting a low CIE-y value can be realized by using a compound having a specific structure, leading to the completion of the present invention.

[0117] The first compound according to one embodiment of the present invention includes a structure in which two fused ring structures (Ar1 and Ar2) are linked by a specific linker (the benzene ring structure shown in formula (1)), and it is believed that the above-mentioned effects can be obtained by employing such a structure. Although the reason for the above-mentioned effect is not entirely clear, it is thought that the bulky shape of a molecule (compound represented by formula (1)) having a structure in which two fused ring structures (Ar1 and Ar2) are bonded at the ortho position on a specific linker having a benzene ring structure suppresses intermolecular interactions, thereby producing the above-mentioned effect. Note that in formula (1), when one or more pairs of adjacent two or more of R1 to R4 are bonded to each other to form a single ring (for example, a naphthalene-2,3-diyl linker (when a pair of R2 and R3 are bonded to each other to form an unsubstituted benzene ring)), the same effect as above is also exhibited.

[0118] Ar1 is a substituted or unsubstituted aryl group having four or more fused monocyclic rings. The monocycle constituting the aryl group is not particularly limited and is usually a 5- to 8-membered monocycle, for example, a 5- or 6-membered monocycle. The multiple monocycles constituting the fused ring structure may be the same or different. The single ring constituting the aryl group is a hydrocarbon structure containing only carbon atoms and hydrogen atoms.

[0119] The number of monocyclic rings constituting the aryl group (the number of condensed monocyclic rings) is not particularly limited as long as it is 4 or more, and is, for example, 4 or more and 6 or less. In one embodiment, the aryl group comprises four or five monocyclic rings.

[0120] Examples of aryl groups in which four monocyclic rings are fused include benzanthracene, benzophenanthrene, pyrene, chrysene, triphenylene, tetracene, benzofluorene, fluoranthene, and structures represented by formulae (TEMP-7) to (TEMP-15) shown in [Definitions].

[0121] Examples of the aryl group in which five single rings are fused include benzochrysene, benzotriphenylene, pentacene, dibenzofluorene, benzofluoranthene, perylene, and structures represented by formulae (TEMP-1) to (TEMP-6) shown in [Definitions].

[0122] In one embodiment, an aryl group having four or more fused monocyclic rings includes a fused ring structure consisting solely of four or more six-membered rings.

[0123] In one embodiment, the aryl group to which four or more monocyclic rings are fused consists solely of a fused ring structure consisting solely of four or more 6-membered rings, i.e., in one embodiment, the aryl group to which four or more monocyclic rings are fused contains no rings other than the 6-membered rings. As is clear from the definition, Ar1 may have, as a substituent, a group containing a ring other than a six-membered ring.

[0124] In one embodiment, Ar1 consists solely of a fused ring structure consisting solely of four six-membered rings.

[0125] In one embodiment, Ar1 is a monovalent group represented by the following formula (11) or (12): [ka] (In equation (11), R 101 ~R 110 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 101 ~R 110 are each independently a hydrogen atom or a substituent R. In equation (12), R 111 ~R 122 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 111 ~R 122 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0126] In one embodiment, R in formula (11) 101 and R 102 represents a single bond to the benzene ring skeleton of formula (1), R does not represent a single bond 101 and R 102 , and R 103 ~R 110 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group. In one embodiment, R in formula (11) 101 represents a single bond to the benzene ring skeleton of formula (1). In one embodiment, R in formula (11) 102 represents a single bond to the benzene ring skeleton of formula (1).

[0127] In one embodiment, R in formula (11) that does not represent a single bond 101 ~R 110 is a hydrogen atom.

[0128] In one embodiment, R in formula (12) 117 and R 122 represents a single bond to the benzene ring skeleton of formula (1), R does not represent a single bond 117 and R 122 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group. In one embodiment, R in formula (12) 117 represents a single bond to the benzene ring skeleton of formula (1). In one embodiment, R in formula (12) 122 represents a single bond to the benzene ring skeleton of formula (1).

[0129] In one embodiment, R in formula (12) that does not represent a single bond 111 ~R 122 is a hydrogen atom.

[0130] Ar2 is a monovalent group represented by formula (21), a monovalent group represented by formula (22), or a substituted or unsubstituted monovalent heterocyclic group having 9 to 50 ring atoms.

[0131] Examples of the substituted or unsubstituted monovalent heterocyclic group having 9 to 50 ring atoms include groups having 9 to 50 ring atoms among specific example group G2 shown in [Definitions].

[0132] In one embodiment, R in formula (21) 201 ~R 210 At least one pair of adjacent pairs of two or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring. In one embodiment, R in formula (21) 201 ~R 210 At least one pair of adjacent two or more of the groups bond to each other to form a substituted or unsubstituted benzene ring. In one embodiment, R in formula (21) 201 ~R 210 One or more pairs of adjacent pairs of the above are not bonded to each other.

[0133] In one embodiment, R in formula (22) 211 ~R 222 One or more pairs of adjacent pairs of the above are not bonded to each other.

[0134] In one embodiment, Ar2 is a monovalent group represented by any of the following formulas (211) to (241). [ka] [In formula (211), R 2111 ~R 2114 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. R 2115 ~R2118 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. R 2119 and R 2120 The group is joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. When the substituted or unsubstituted benzene ring is formed, one of the atoms forming the benzene ring is bonded to the benzene ring skeleton of formula (1), or R 2111 ~R 2118 One of these represents a single bond to the benzene ring skeleton of formula (1). When the substituted or unsubstituted benzene ring is not formed, R 2111 ~R 2118 One of these represents a single bond to the benzene ring skeleton of formula (1). R that does not form the single ring or the fused ring 2119 and R 2120 and R which does not form a substituted or unsubstituted benzene ring and does not represent a single bond. 2111 ~R 2118 are each independently a hydrogen atom or a substituent R. In equation (221), R 2211 ~R 2222 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2211 ~R 2222 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2211 ~R 2222 are each independently a hydrogen atom or a substituent R. In equation (231), R 2311 ~R 2320One or more pairs of adjacent pairs of the above are not bonded to each other. R 2311 ~R 2320 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2311 ~R 2320 are each independently a hydrogen atom or a substituent R. In equation (241), X 2411 is N(R 2419 ), O, or S. R 2411 ~R 2414 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. R 2415 ~R 2418 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. When the substituted or unsubstituted benzene ring is formed, one of the atoms forming the benzene ring is bonded to the benzene ring skeleton of formula (1), or R 2419 and R that does not form the benzene ring 2411 ~R 2418 One of these represents a single bond to the benzene ring skeleton of formula (1). When the substituted or unsubstituted benzene ring is not formed, R 2411 ~R 2419 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2419 and R which does not form a benzene ring and does not represent a single bond. 2411 ~R 2418 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0135] In one embodiment, R in formula (211) 2119 and R 2120 are each independently, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, or It is a substituted or unsubstituted naphthyl group.

[0136] In one embodiment, R in formula (221) 2217 and R 2222 represents a single bond to the benzene ring skeleton of formula (1), R does not represent a single bond 2217 and R 2222 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0137] In one embodiment, X in formula (241) 2411 is O or S, R 2411 ~R 2414 one or more pairs of adjacent pairs of R 2415 ~R 2418 one or more pairs of adjacent pairs of R 2411 ~R 2418 represents a single bond to the benzene ring skeleton of formula (1), R does not represent a single bond 2111 ~R 2118 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0138] In one embodiment, X in formula (241) 2411 is O or S, R 2411 ~R 2414 one or more pairs of adjacent pairs of R 2415 ~R 2418one or more pairs of adjacent two or more of R 2411 ~R 2414 represents a single bond to the benzene ring skeleton of formula (1), R does not represent a single bond 2411 ~R 2414 and R that does not form a benzene ring. 2415 ~R 2418 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0139] In one embodiment, X in formula (241) 2411 is O.

[0140] In one embodiment, R in formula (241) that does not represent a single bond 2411 ~R 2414 and R that does not form a benzene ring 2415 ~R 2418 is a hydrogen atom.

[0141] In one embodiment, the compound represented by formula (1) is a compound represented by any one of the following formulas (1-1) to (1-6). [ka] [ka] [ka] R1 to R4 are as defined in the formula (1) above. R 101 ~R 110 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 101 ~R 110 are each independently a hydrogen atom or a substituent R. R 2211 ~R 2222One or more pairs of adjacent pairs of the above are not bonded to each other. R 2211 ~R 2222 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 2211 ~R 2222 are each independently a hydrogen atom or a substituent R. In formula (1-2), R1 to R4 are as defined in the formula (1) above. R 111 ~R 122 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 111 ~R 122 are each independently a hydrogen atom or a substituent R. X 2411 is N(R 2419 ), O, or S. R 2411 ~R 2414 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. R 2415 ~R 2418 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. When the substituted or unsubstituted benzene ring is formed, one of the atoms forming the benzene ring is bonded to the benzene ring skeleton outside the brackets, or R 2419 and R that does not form the benzene ring 2411 ~R 2418 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. When the substituted or unsubstituted benzene ring is not formed, R 2411 ~R 2419 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond2419 and R which does not form a benzene ring and does not represent a single bond. 2411 ~R 2418 are each independently a hydrogen atom or a substituent R. In formula (1-3), R1 to R4 are as defined in the formula (1) above. R 101 ~R 110 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 101 ~R 110 are each independently a hydrogen atom or a substituent R. R 2311 ~R 2320 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2311 ~R 2320 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2311 ~R 2320 are each independently a hydrogen atom or a substituent R. In formula (1-4), R1 to R4 are as defined in the formula (1) above. R 111 ~R 122 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 111 ~R 122 are each independently a hydrogen atom or a substituent R. R 2211 ~R 2222 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2211 ~R 2222 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2211 ~R 2222 are each independently a hydrogen atom or a substituent R. In formula (1-5), R1 to R4 are as defined in the formula (1) above. R 101 ~R 110 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 101 ~R 110 are each independently a hydrogen atom or a substituent R. X 2411 is N(R 2419 ), O, or S. R 2411 ~R 2414 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. R 2415 ~R 2418 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. When the substituted or unsubstituted benzene ring is formed, one of the atoms forming the benzene ring is bonded to the benzene ring skeleton outside the brackets, or R 2419 and R that does not form the benzene ring 2411 ~R 2418 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. When the substituted or unsubstituted benzene ring is not formed, R 2411 ~R 2419 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 2419 and R which does not form a benzene ring and does not represent a single bond. 2411 ~R 2418 are each independently a hydrogen atom or a substituent R. In formula (1-6), R1 to R4 are as defined in the formula (1) above. R 111 ~R 122One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 111 ~R 122 are each independently a hydrogen atom or a substituent R. R 2311 ~R 2320 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2311 ~R 2320 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2311 ~R 2320 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0142] In one embodiment, the compound represented by formula (1) is a compound represented by any one of the following formulas (1-1-1) to (1-6-1). [ka] [ka] [ka] [In formula (1-1-1), R1 to R4 are as defined in the formula (1) above. R 101 ~R 102 and R 104 ~R 110 are each independently a hydrogen atom or a substituent R. R 2231 ~R 2242 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2237 and R 2242 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 2237 and R 2242 , and R2231 ~R 2236 and R 2238 ~R 2241 are each independently a hydrogen atom or a substituent R. In formulas (1-2-1) and (1-2-2), R1 to R4 are as defined in the formula (1) above. R 111 ~R 122 are each independently a hydrogen atom or a substituent R. X 2411 is N(R 2419 ), O, or S. R 2421 ~R 2424 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. R 2425 ~R 2428 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. When the substituted or unsubstituted benzene ring is formed, one of the atoms forming the benzene ring is bonded to the benzene ring skeleton outside the brackets, or R 2419 and R that does not form the benzene ring 2421 ~R 2428 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. When the substituted or unsubstituted benzene ring is not formed, R 2419 and R 2421 ~R 2428 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 2419 and R which does not form a benzene ring and does not represent a single bond. 2421 ~R 2428 are each independently a hydrogen atom or a substituent R. In formula (1-3-1), R1 to R4 are as defined in the formula (1) above. R 101 ~R 102 and R 104 ~R 110 are each independently a hydrogen atom or a substituent R. R 2311 ~R 2320 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2311 ~R 2320 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2311 ~R 2320 are each independently a hydrogen atom or a substituent R. In formula (1-4-1), R1 to R4 are as defined in the formula (1) above. R 111 ~R 116 and R 118 ~R 122 are each independently a hydrogen atom or a substituent R. R 2211 ~R 2222 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2211 ~R 2222 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2211 ~R 2222 are each independently a hydrogen atom or a substituent R. In formula (1-5-1), R1 to R4 are as defined in the formula (1) above. R 101 ~R 102 and R 104 ~R 110 are each independently a hydrogen atom or a substituent R. X 2411 is N(R 2419 ), O, or S. R 2411 ~R 2414At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. R 2415 ~R 2418 At least one pair of adjacent pairs of combine with each other to form a substituted or unsubstituted benzene ring, or Do not bond with each other. When the substituted or unsubstituted benzene ring is formed, one of the atoms forming the benzene ring is bonded to the benzene ring skeleton outside the brackets, or R 2419 and R that does not form the benzene ring 2411 ~R 2418 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. When the substituted or unsubstituted benzene ring is not formed, R 2411 ~R 2419 One of the brackets represents a single bond to the benzene ring skeleton outside the brackets. R does not represent a single bond 2419 and R which does not form a benzene ring and does not represent a single bond. 2411 ~R 2418 are each independently a hydrogen atom or a substituent R. In formula (1-6-1), R1 to R4 are as defined in the formula (1) above. R 111 ~R 116 and R 118 ~R 122 are each independently a hydrogen atom or a substituent R. R 2311 ~R 2320 One or more pairs of adjacent pairs of the above are not bonded to each other. R 2311 ~R 2320 One of these represents a single bond to the benzene ring skeleton of formula (1). R does not represent a single bond 2311 ~R 2320 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0143] In one embodiment, the compound represented by formula (1) is a compound represented by any one of the following formulas (1-11) to (1-30). [ka] [ka] [ka] [ka] [ka] [ka] [ka] [In formulas (1-11) to (1-30), R1 to R4 are as defined in the formula (1) above. X 61 , X 91 , and X 2411 are each independently O or S. R 11 ~R 19 , R 21 ~R 32 , R 41 ~R 51 , R 61 ~R 67 , R 71 ~R 81 , R 91 ~R 94 , R 97 ~R 99 , R 101 ~R 102 , R 104 ~R 110 , R 111 ~R 122 , R 2211 ~R 2222 , R2311 ~R 2313 , R 2315 ~R 2320 , R 2421 ~R 2424 , R 2425 ~R 2428 , and R 2431 ~R 2434 are each independently a hydrogen atom or a substituent R. The substituent R is as defined in formula (1).

[0144] In one embodiment, R 11 ~R 19 , R 21 ~R 32 , R 41 ~R 51 , R 61 ~R 67 , R 71 ~R 81 , R 91 ~R 94 , R 97 ~R 99 , R 93a ~R 98a , R 101 ~R 102 , R 104 ~R 110 , R 111 ~R 122 , R 2211 ~R 2222 , R 2311 ~R 2313 , R 2315 ~R 2320 , R 2421 ~R 2424 , R 2425 ~R 2428 , and R 2431 ~R 2434 is a hydrogen atom.

[0145] In one embodiment, R1 to R4 are hydrogen atoms, a substituted or unsubstituted phenyl group, or It is a substituted or unsubstituted naphthyl group.

[0146] In one embodiment, R1 to R4 are hydrogen atoms.

[0147] In one embodiment, the compound represented by formula (1) has at least one deuterium atom.

[0148] As used herein, a compound "having a deuterium atom" means that the compound has at least one hydrogen atom, and that the ratio of deuterium atoms to the total of protons and deuterium atoms is higher than the natural abundance ratio of the hydrogen atoms. The fact that the ratio of deuterium atoms to the total of protons and deuterium atoms is higher than the natural abundance ratio can be confirmed by nuclear magnetic resonance spectroscopy.

[0149] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (1) is an alkyl group having 1 to 50 carbon atoms; an alkenyl group having 2 to 50 carbon atoms; an alkynyl group having 2 to 50 carbon atoms; a cycloalkyl group having 3 to 50 ring carbon atoms, -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 aryl group having 6 to 50 ring carbon atoms, or It is a heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0150] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (1) 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

[0151] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (1) 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:

[0152] In one embodiment, the compound of formula (1) comprises a deuterium atom.

[0153] In one embodiment, Ar1 has a deuterium atom. In one embodiment, Ar2 contains a deuterium atom.

[0154] In one embodiment, R1 to R4 that are hydrogen atoms are deuterium atoms.

[0155] In one embodiment, Ar1 has a deuterium atom and the hydrogen atom carried by Ar2 is a proton atom.

[0156] In one embodiment, Ar1 has a deuterium atom, the hydrogen atoms of the monocyclic ring formed by R1 to R4 are proton atoms, and R1 to R4 that are hydrogen atoms are proton atoms.

[0157] In one embodiment, Ar2 has a deuterium atom, and R1 to R4 that are hydrogen atoms are deuterium atoms.

[0158] In one embodiment, Ar1 has a deuterium atom, Ar2 has a deuterium atom, and R1 to R4 that are hydrogen atoms are deuterium atoms.

[0159] In one embodiment, Ar1 has a deuterium atom, the hydrogen atom possessed by Ar2 is a proton atom, the hydrogen atom possessed by the monocycle formed by R1 to R4 is a proton atom, and the hydrogen atoms possessed by R1 to R4 are proton atoms.

[0160] As used herein, a compound or group "having a deuterium atom" means that, among the hydrogen atoms contained in the compound or group, the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is higher than the natural abundance ratio for at least one hydrogen atom.

[0161] In this specification, a specific hydrogen atom (or a hydrogen atom R x (X is an integer that identifies the substituent) is "a deuterium atom" means that the proportion of deuterium atoms relative to the total of protium atoms and deuterium atoms in the hydrogen atom is higher than the natural abundance ratio. The fact that the ratio of deuterium atoms to the total of protium and deuterium atoms is higher than the natural abundance ratio can be confirmed by a nuclear magnetic resonance spectrometer.

[0162] The first compound according to one embodiment of the present invention can be synthesized by following the examples and using known alternative reactions and raw materials suited to the target compound.

[0163] Specific examples of the first compound according to one embodiment of the present invention are described below, but these are merely illustrative, and the first compound according to one embodiment of the present invention is not limited to the following specific examples. For example, among the specific examples of the second compound and the third compound described below, the compound represented by formula (1) can be used as the first compound.

[0164] [ka] [ka]

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[0165] [Second compound] A second compound according to one aspect of the present invention is represented by the following formula (3). [ka] [In formula (3), R 301 ~R 312 At least one of the above is a group represented by the following formula (31). R that is not a group represented by the formula (31) 301 ~R 312 are each independently a hydrogen atom or a substituent R. However, R 307 is a group represented by the formula (31), R 301 ~R 312 are each independently a hydrogen atom or a substituent Q. R 301 ~R 312 One or more pairs of adjacent pairs of the above are not bonded to each other. [ka] (In equation (31), L 301 teeth, single bond, a substituted or unsubstituted phenylene group, or It is a substituted or unsubstituted naphthalenediyl group. n301 is an integer of 0 to 3. If n301 is 0, then (L 301 ) n301 is a single bond. If n301 is 2 or more, L is 2 or more 301 are connected in series. When n301 is 2 or more, L 301 may be the same as or different from each other. Ar 301represents an unsubstituted aryl group having 6 to 15 ring carbon atoms. n302 is an integer of 1 to 3. If n302 is 2 or more, then 2 or more Ar 301 may be the same as or different from each other. X 301 is C(R 329 )(R 330 ), N(R 331 ), O, or S. R 321 ~R 331 One of them is L 301 represents a single bond that connects to R does not represent a single bond 321 ~R 328 Of these, n302 are Ar 301 represents a single bond that connects to R does not represent a single bond 321 ~R 331 are each independently a hydrogen atom or a substituent R. R 329 and R 330 pairs are disjoint.) The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different. The substituent Q 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 ), a halogen atom, a cyano group, a nitro group, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 is as defined for the substituent R. When two or more substituents Q are present, the two or more substituents Q may be the same or different.]

[0166] When the second compound according to one embodiment of the present invention is used in an organic layer of an organic EL device, the device performance can be improved, for example, an organic EL device having a low driving voltage, a high external quantum efficiency, and a long device life can be realized.

[0167] The driving voltage, external quantum efficiency, and device life of the organic EL device are measured by the methods described in the Examples.

[0168] In equation (31), when n301 is 0, (L 301 ) n301 is a single bond. In addition, in formula (31), R 321 ~R 331 One of them is L 301 represents a single bond that connects to That is, if n301 is 0, R 321 ~R 331 One of these represents a single bond that connects to the anthracene skeleton of formula (3). For example, R 307 is a structure represented by formula (31), n301 is 0, and R 324 L 301 represents a single bond bonded to, n302 is 1, and R 327 Ar 301 When the compound represented by formula (3) represents a single bond bonded to the group, the compound represented by formula (3) is represented by the following formula (3-E). [ka]

[0169] In one embodiment, L 301 is a single bond or a substituted or unsubstituted phenylene group. In one embodiment, L 301 is a single bond.

[0170] In one embodiment, n301 is 0 or 1. In one embodiment, n301 is 0.

[0171] In one embodiment, R 321 ~R324 One of them is L 301 represents a single bond that binds to In one embodiment, R 323 and R 324 One of them is L 301 represents a single bond that binds to In one embodiment, R 324 L 301 represents a single bond that connects to

[0172] In one embodiment, Ar 301 teeth, an unsubstituted phenyl group, an unsubstituted o-biphenyl group, an unsubstituted m-biphenyl group, an unsubstituted p-biphenyl group, or It is an unsubstituted naphthyl group.

[0173] In one embodiment, n302 is 1 or 2. In one embodiment, n302 is 1.

[0174] In one embodiment, R 325 ~R 328 One of them is Ar 301 represents a single bond that connects to In one embodiment, R 327 Ar 301 represents a single bond that connects to

[0175] In one embodiment, X 301 is C(R 329 )(R 330 ) or O. In one embodiment, X 301 is O.

[0176] In one embodiment, R does not represent a single bond. 321 ~R 331 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0177] In one embodiment, R does not represent a single bond. 321 ~R 328 is a hydrogen atom.

[0178] In one embodiment, R is a hydrogen atom. 301 ~R 312 , R is the substituent R 301 ~R 312 a hydrogen atom possessed by R is a substituent Q 301 ~R 312 a hydrogen atom possessed by L 301 a hydrogen atom possessed by R is a hydrogen atom 321 ~R 331 , Ar 301 and a hydrogen atom in R is the substituent R 329 ~R 331 The hydrogen atom One or more hydrogen atoms selected from the group consisting of are deuterium atoms.

[0179] In one embodiment, R is a hydrogen atom. 301 ~R 312 , R is the substituent R 301 ~R 312 a hydrogen atom possessed by R is a substituent Q 301 ~R 312 a hydrogen atom possessed by wherein one or more hydrogen atoms selected from the group consisting of are deuterium atoms; L 301 a hydrogen atom possessed by R is a hydrogen atom 321 ~R 331 , Ar 301 and a hydrogen atom in R is the substituent R 329 ~R 331 The hydrogen atom possessed by is a proton atom. In other words, in one embodiment, at least one of the hydrogen atoms in the anthracene skeleton of formula (3) is a deuterium atom, and the hydrogen atom in the group represented by formula (31) is a proton atom.

[0180] As used herein, the expression "a hydrogen atom is a deuterium atom" means that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms in the hydrogen atom is greater than the natural abundance. The fact that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is greater than the natural abundance can be confirmed by a nuclear magnetic resonance spectrometer.

[0181] As used herein, the expression "a proton atom" means that the proportion of deuterium atoms relative to the total of proton atoms and deuterium atoms in the hydrogen atom is lower than the natural abundance. The fact that the proportion of deuterium atoms relative to the total of proton atoms and deuterium atoms is lower than the natural abundance can be confirmed by a nuclear magnetic resonance spectrometer.

[0182] In one embodiment, R 304 , R 306 , R 307 , R 311 , and R 312 At least one of the groups is a group represented by the formula (31). In one embodiment, R 307 and R 312 At least one of the groups is a group represented by the formula (31). In one embodiment, R 307 is a group represented by the formula (31).

[0183] In one embodiment, R is not a group represented by formula (31). 301 ~R 312 is a hydrogen atom.

[0184] In one embodiment, the compound represented by formula (3) is a compound represented by any one of the following formulas (3-1) to (3-5). [ka] [ka] [In formulas (3-1) to (3-5), R 301 ~R 312 , L 301 , n301, n302, Ar 301 , X 301 , and R 321 ~R 328 is as defined in the above formula (3).

[0185] In one embodiment, the compound represented by formula (3) is a compound represented by any one of the following formulas (3-11) to (3-21), (3-31), (3-41) to (3-46), and (3-51) to (3-52). [ka] [ka] [ka] [ka] [ka] [ka] [ka] [In formulas (3-11) to (3-21), formula (3-31), formula (3-41) to (3-46), and formulas (3-51) to (3-52), R 301 ~R 312 , L 301 , n301, Ar 301 , X 301 , and R 321 ~R 328is as defined in the above formula (3).

[0186] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (3) is an alkyl group having 1 to 50 carbon atoms; an alkenyl group having 2 to 50 carbon atoms; an alkynyl group having 2 to 50 carbon atoms; a cycloalkyl group having 3 to 50 ring carbon atoms, -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 aryl group having 6 to 50 ring carbon atoms, or It is a heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0187] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (3) 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

[0188] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (3) 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:

[0189] The second compound according to one embodiment of the present invention can be synthesized by following the examples and using known alternative reactions and raw materials suited to the target compound.

[0190] Specific examples of the second compound according to one embodiment of the present invention are described below, but these are merely illustrative, and the second compound according to one embodiment of the present invention is not limited to the following specific examples. For example, among the specific examples of the first compound described above and the specific examples of the third compound described below, the compound represented by formula (3) can be used as the second compound.

[0191] In one embodiment, the compound of formula (3) does not include any overlapping range with the compound of formula (1).

[0192] In one embodiment, the compound represented by formula (3) does not include the specific examples of the first compound described above. In this embodiment, the compound represented by formula (3) is a compound other than the specific examples of the first compound described above.

[0193] [ka] [ka] [ka] [ka] [ka] [ka]

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[0194] [Third compound] A third compound according to one embodiment of the present invention is represented by formula (4). [ka] [In formula (4), R 401 ~R 412 At least one of the above is a group represented by the following formula (41). R that is not a group represented by the formula (41) 401 ~R 412 are each independently a hydrogen atom or a substituent R. R 401 ~R 412 One or more pairs of adjacent pairs of the above are not bonded to each other. [ka] (In equation (41), L 401 teeth, single bond, a substituted or unsubstituted phenylene group, or It is a substituted or unsubstituted naphthalenediyl group. n401 is an integer of 0 to 3. If n401 is 0, then (L 401 ) n401 is a single bond. If n401 is 2 or more, L is 2 or more. 401 are connected in series. When n401 is 2 or more, L 401 may be the same as or different from each other. Ar 401 represents an unsubstituted aryl group having 6 to 15 ring carbon atoms. n402 is an integer of 1 to 3. If n402 is 2 or more, then 2 or more Ar 401 may be the same as or different from each other. X 401 is C(R 429 )(R 430 ), N(R 431 ), O, or S. R 421 ~R 431 One of them is L 401 represents a single bond that connects to R does not represent a single bond 421 ~R 428 Of these, n402 are Ar 401 represents a single bond that connects to R does not represent a single bond 421 ~R 431 are each independently a hydrogen atom or a substituent R. R 429 and R 430 pairs are disjoint.) The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 If there are two or more, there are two or more R 901 ~R 907 may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different. However, R is a hydrogen atom. 401 ~R 412 , R is the substituent R 401 ~R 412 a hydrogen atom possessed by L 401 a hydrogen atom possessed by R is a hydrogen atom 421 ~R 431 , Ar 401 and a hydrogen atom in R is the substituent R 429 ~R 431 The hydrogen atom wherein one or more hydrogen atoms selected from the group consisting of are deuterium atoms.

[0195] When the third compound according to one embodiment of the present invention is used in an organic layer of an organic EL device, the device performance can be improved, for example, an organic EL device having a low driving voltage, a high external quantum efficiency, and a long device life can be realized.

[0196] The driving voltage, external quantum efficiency, and device life of the organic EL device are measured by the methods described in the Examples.

[0197] In equation (41), when n401 is 0, (L 401 ) n401 is a single bond. In addition, in formula (41), R 421 ~R 431 One of them is L 401 represents a single bond that connects to That is, if n401 is 0, R 421 ~R 431 One of these represents a single bond that connects to the anthracene skeleton of formula (4). For example, R 407 is a structure represented by formula (41), n401 is 0, and R 424 L 401 represents a single bond bonded to, n402 is 1, and R 427 Ar 401 When the compound represented by formula (4) represents a single bond bonded to the group, the compound represented by formula (4-E) is represented by the following formula (4-E). [ka]

[0198] In one embodiment, X 401 is C(R 429 )(R 430 ) or O. In one embodiment, X 401 is O.

[0199] In one embodiment, L 401 is a single bond or a substituted or unsubstituted phenylene group. In one embodiment, L 401 is a single bond.

[0200] In one embodiment, Ar 401 teeth, an unsubstituted phenyl group, an unsubstituted o-biphenyl group, an unsubstituted m-biphenyl group, an unsubstituted p-biphenyl group, or It is an unsubstituted naphthyl group.

[0201] In one embodiment, n401 is 0 or 1. In one embodiment, n401 is 0.

[0202] In one embodiment, n402 is 1 or 2. In one embodiment, n402 is 1.

[0203] In one embodiment, R 425 ~R 428 One of them is Ar 401 represents a single bond that connects to In one embodiment, R 427 Ar 401 represents a single bond that connects to

[0204] In one embodiment, R does not represent a single bond. 421 ~R 431 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0205] In one embodiment, R does not represent a single bond. 421 ~R 428 is a hydrogen atom.

[0206] In one embodiment, R is a hydrogen atom. 401 ~R 412 , R is the substituent R 401 ~R 412 a hydrogen atom possessed by wherein one or more hydrogen atoms selected from the group consisting of are deuterium atoms; L 401 a hydrogen atom possessed by R is a hydrogen atom 421 ~R 431 , Ar 401 and a hydrogen atom in R is the substituent R 429 ~R 431 The hydrogen atom possessed by is a proton atom.

[0207] In one embodiment, R 407 and R 412 At least one of the groups is a group represented by the formula (41). In one embodiment, R 407 is a group represented by the formula (41).

[0208] In one embodiment, R is not a group represented by formula (41). 401 ~R 412 is a hydrogen atom.

[0209] In one embodiment, R 423 and R 424 One of them is L 401 represents a single bond that connects to In one embodiment, R 424 L 401 represents a single bond that connects to

[0210] In one embodiment, the compound represented by formula (4) is a compound represented by any one of the following formulas (4-1) to (4-5). [ka] [ka] [In formulas (4-1) to (4-5), R 401 ~R 412 , L 401 , n401, n402, Ar 401 , X401 , and R 421 ~R 428 is as defined in the above formula (4).

[0211] In one embodiment, the compound represented by formula (4) is a compound represented by any one of the following formulas (4-11) to (4-12), (4-21), (4-31), and (4-42) to (4-43). [ka] [ka] [In formulas (4-11) to (4-12), formula (4-21), formula (4-31), and formulas (4-42) to (4-43), R 401 ~R 412 , L 401 , n401, Ar 401 , X 401 , R 421 ~R 423 , and R 425 ~R 428 is as defined in the above formula (4).

[0212] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (4) is an alkyl group having 1 to 50 carbon atoms; an alkenyl group having 2 to 50 carbon atoms; an alkynyl group having 2 to 50 carbon atoms; a cycloalkyl group having 3 to 50 ring carbon atoms, -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 aryl group having 6 to 50 ring carbon atoms, or It is a heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0213] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (4) 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

[0214] In one embodiment, the substituent in the term "substituted or unsubstituted" in formula (4) 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:

[0215] The third compound according to one embodiment of the present invention can be synthesized by following the examples and using known alternative reactions and raw materials suited to the target compound.

[0216] Specific examples of the third compound according to one embodiment of the present invention are described below, but these are merely illustrative, and the third compound according to one embodiment of the present invention is not limited to the following specific examples. For example, among the specific examples of the first compound and the second compound described above, the compound represented by formula (4) can be used as the third compound.

[0217] In one embodiment, the compound of formula (4) does not include any overlapping range with the compound of formula (1).

[0218] In one embodiment, the compound represented by formula (4) does not include the specific examples of the first compound described above. In this embodiment, the compound represented by formula (4) is a compound other than the specific examples of the first compound described above.

[0219] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0220] [Materials for organic electroluminescence devices] The compound according to one embodiment of the present invention (including the first compound, the second compound, and the third compound described above; the same applies hereinafter) 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.

[0221] [Organic EL element] An organic EL device according to one embodiment of the present invention includes 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 (a compound represented by formula (1), a compound represented by formula (3), or a compound represented by formula (4)).

[0222] The organic EL device according to one embodiment of the present invention has the above-described structure, thereby improving its performance. For example, the compound represented by formula (1) can realize an organic EL device with a low driving voltage, a high external quantum efficiency, and a low CIE-y. Furthermore, the compound represented by formula (3) or (4) can realize an organic EL device with a low driving voltage, a high external quantum efficiency, and a long device life.

[0223] The organic EL device according to one embodiment of the present invention has one or more organic layers disposed between a cathode and the anode. At least one of the organic layers contains a compound according to one embodiment of the present invention. Conventionally known materials and device configurations can be used in the organic EL device according to the present invention, as long as the effects of the present invention are not impaired.

[0224] In one embodiment, the organic EL device of the present invention comprises an anode, an emitting layer, and a cathode in this order, and at least one of the organic layers in the emitting layer comprises the compound.

[0225] In one embodiment, in the organic EL device according to one aspect of the present invention, the light-emitting layer includes, from the anode side, a first layer and a second layer, and the first layer includes the compound.

[0226] In one embodiment, in the organic EL device according to one aspect of the present invention, the light-emitting layer further contains a compound represented by any one of the following formulas (D11) to (D41). [ka]

[0227] Equations (D11) to (D41) will be described later.

[0228] (Compound represented by formula (D11)) The compound represented by formula (D11) will be explained. [ka] [In formula (D11), The three Zs are independently a or a nitrogen atom. Ring A1 and ring A2 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. R a If there are multiple R a One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. nD11 and nD12 are each independently 0, 1, 2, 3, or 4. R b If there are multiple R b One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. R cIf there are multiple R c One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. R that does not form the single ring or the fused ring a , R b , and R c are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 is as defined in the above formula (1).

[0229] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms." The "aromatic hydrocarbon ring" of ring A1 and ring A2 contains, as ring-forming atoms, the two carbon atoms on the central fused two-ring structure of formula (D11). Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "substituted or unsubstituted aryl group" described in specific example group G1.

[0230] The "heterocyclic ring" of ring A1 and ring A2 has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group having 5 to 50 ring atoms." The "heterocycle" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of formula (D11) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms" include compounds in which a hydrogen atom is introduced into the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0231] Rb is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A1, or any of the atoms forming the heterocycle as ring A1.

[0232] Rc is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A2, or any of the atoms forming the heterocycle as ring A2.

[0233] In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D11a): In one embodiment, at least two of Ra, Rb, and Rc are groups represented by the following formula (D11a):

[0234] [ka] [In formula (D11a), L D101 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms. Ar D101 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or It is a group represented by the following formula (D11b). [ka] (In formula (D11b), L D102 and L D103 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or It is a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms. Ar D102 and Ar D103 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. Ar which does not form the single ring or condensed ring D102 and Ar D103 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.)

[0235] Specific examples of the compound represented by formula (D11) are listed below, but these are merely illustrative, and the compound represented by formula (D11) is not limited to the following specific examples.

[0236] [ka]

[0237] (Compound represented by formula (D21)) The compound represented by formula (D21) will be explained. [ka] [In formula (D21), R D201 and R D202 , R D202 and R D203 , and R D203 and R D204 At least one pair of these bonds together to form a divalent group represented by the following formula (D22). R D205 and R D206 , R D206 and R D207 , and R D207 and R D208 At least one pair of these bonds together to form a divalent group represented by the following formula (D23). [ka] (R D211 ~R D214 and R that does not form a divalent group represented by formula (D22). D201 ~R D204 At least one of the above is a monovalent group represented by the following formula (D24). R D221 ~R D224 and R which does not form a divalent group represented by formula (D23). D205 ~R D208 At least one of the above is a monovalent group represented by the following formula (D24). X D2 is an oxygen atom, a sulfur atom, or NR D209 is. R which does not form a divalent group represented by the formula (D22) or the formula (D23) and is not a monovalent group represented by the formula (D24) D201 ~R D208 R which is not a monovalent group represented by formula (D24) D211 ~R D214 and R D221 ~R D224 , and R D209 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. [ka] (In formula (D24), Ar D201 and Ar D202 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. L D201 ~L D203 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or It is a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 30 ring carbon atoms and substituted or unsubstituted divalent heterocyclic groups having 5 to 30 ring atoms. * indicates the bonding position to the ring structure represented by formula (D21) or the group represented by formula (D22) or formula (D23). R 901 ~R 907is as defined in the above formula (1).

[0238] In formula (D21), the positions at which the divalent group represented by formula (D22) and the divalent group represented by formula (D23) are formed are not particularly limited, and R D201 ~R D208 The group can be formed at any possible position.

[0239] Specific examples of the compound represented by formula (D21) include the compounds described in WO 2014 / 104144 and the compounds shown below, but these are merely examples, and the compound represented by formula (21) is not limited to the specific examples below.

[0240] [ka]

[0241] (Compound represented by formula (D31)) The compound represented by formula (D31) will be explained. [ka] [In formula (D31), R D301 ~R D307 and R D311 ~R D317 At least one pair of adjacent two or more of these may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other. R that does not form the single ring or the fused ring D301 ~R D307 and R D311 ~R D317 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R D321 and R D322 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 is as defined in the above formula (1).

[0242] "R D301 ~R D307 and R D311 ~RD317 "A set consisting of two or more adjacent ones of" is, for example, R D301 and R D302 A set consisting of R D302 and R D303 A set consisting of R D303 and R D304 A set consisting of R D305 and R D306 A set consisting of R D306 and R D307 A set consisting of R D301 and R D302 and R D303 It is a combination of a set consisting of:

[0243] In one embodiment, R D301 ~R D307 and R D311 ~R D317 At least one of -N(R 906 )(R 907 ) In one embodiment, R D301 ~R D307 and R D311 ~R D317 The two are -N(R 906 )(R 907 )

[0244] In one embodiment, R D301 ~R D307 and R D311 ~R D317 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0245] Specific examples of the compound represented by formula (D31) are listed below, but these are merely illustrative, and the compound represented by formula (D31) is not limited to the following specific examples.

[0246] [ka] [ka]

[0247] (Compound represented by formula (D41)) The compound represented by formula (D41) will be explained. [ka] [In formula (D41), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. R D401 and R D402 each independently bonds to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or does not bond to the ring a, ring b, or ring c. R that does not form a heterocyclic ring D401 and R D402 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.]

[0248] Ring a, ring b, and ring c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms) fused to the central fused bicyclic structure of formula (D41) composed of a B atom and two N atoms.

[0249] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. The "aromatic hydrocarbon rings" of rings b and c contain two carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. Specific examples of "substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1. The "heterocycles" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group." The "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. The "heterocycles" of ring b and ring c contain two carbon atoms on the central fused bicyclic structure of formula (D41) as ring-forming atoms. Specific examples of "substituted or unsubstituted heterocycles having 5 to 50 ring-forming atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.

[0250] R D401 and R D402 may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring contains the nitrogen atom on the central fused bicyclic structure of formula (D41). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. R D401 and R D402 is bonded to ring a, ring b, or ring c specifically means that an atom constituting ring a, ring b, or ring c is bonded to R D401 and R D402 It means that the atoms that make up R are bonded together. D401 is bonded to the a ring, and R D401 and ring a may be fused to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. R D401 When is bonded to ring b, R D402When R is bonded to ring a, D402 The same applies when is bonded to ring c.

[0251] In one embodiment, ring a, ring b, and ring c in formula (D41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. In one embodiment, ring a, ring b, and ring c in formula (D41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0252] In one embodiment, R in formula (D41) D401 and R D402 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, and are preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0253] In one embodiment, the compound represented by formula (D41) is a compound represented by formula (D42): [ka] (In formula (D42), R D401A is R D411 and R D421 R is bonded to one or more selected from the group consisting of D402A is R D413 and R D414 may be bonded to one or more selected from the group consisting of: to form a substituted or unsubstituted heterocycle, or may not be bonded at all. R that does not form the substituted or unsubstituted heterocycle D401A and R D402A are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R D411 ~R D421 One or more pairs of two or more adjacent groups among these may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not be bonded to each other. R that does not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted saturated or unsaturated ring D411 ~R D421 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 is as defined in the above formula (1).

[0254] R in formula (D42) D401A and R D402A is R in equation (D41). D401 and R D402 is a group corresponding to For example, RD401A and R D411 may be bonded to form a two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring in which a ring containing the ring is fused with a benzene ring corresponding to ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. D401A and R D412 If R D402A and R D413 When R is bonded, D402A and R D414 The same applies when the two are combined.

[0255] R D411 ~R D421 One or more pairs of two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. For example, R D411 and R D412 may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused to the six-membered ring to which they are bonded, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0256] In one embodiment, R that does not contribute to ring formation D411 ~R D421 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0257] In one embodiment, R that does not contribute to ring formation D411 ~R D421 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0258] In one embodiment, R that does not contribute to ring formation D411 ~R D421are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0259] In one embodiment, R that does not contribute to ring formation D411 ~R D421 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R D411 ~R D421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0260] In one embodiment, the compound represented by formula (D42) is a compound represented by formula (D43): [ka] (In formula (D43), R D431 is R D446 R may be bonded to form a substituted or unsubstituted heterocycle, or may not be bonded at all. D433 is R D447 R may be bonded to form a substituted or unsubstituted heterocycle, or may not be bonded at all. D434 is R D451 R may be bonded to form a substituted or unsubstituted heterocycle, or may not be bonded at all. D441 is R D442 may be bonded to form a substituted or unsubstituted heterocycle, or may not be bonded at all. R D431 ~R D451 One or more pairs of two or more adjacent groups among these may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not be bonded to each other. R that does not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted saturated or unsaturated ring D431 ~R D451 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R 901 ~R 907 is as defined in the above formula (1).

[0261] R D431 is R D446 may be bonded to form a substituted or unsubstituted heterocycle. For example, R D431 and R D446 are combined to form R D446 The benzene ring to which R is bonded, the ring containing N, and the benzene ring corresponding to ring a may be condensed to form a nitrogen-containing heterocyclic ring having three or more condensed rings. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more condensed rings in the specific example group G2. D433 and R D447 If R D434 and R D451 When R is bonded, D441 and R D442 The same applies when the two are combined.

[0262] In one embodiment, R that does not contribute to ring formation D431 ~R D451are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0263] In one embodiment, R that does not contribute to ring formation D431 ~R D451 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0264] In one embodiment, R that does not contribute to ring formation D431 ~R D451 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0265] In one embodiment, R that does not contribute to ring formation D431 ~R D451 are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and R D431 ~R D451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0266] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43A): [ka] (In formula (D43A), R D461 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R D462 ~R D465 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0267] In one embodiment, R D461 ~R D465 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 50 ring carbon atoms.

[0268] In one embodiment, R D461 ~R D465 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0269] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43B): [ka] (In formula (D43B), R D471 and R D472 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ), or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R D473 ~R D475 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ), or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R 906 and R 907 is as defined in the above formula (1).

[0270] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43B'): [ka] (In formula (D43B'), R D472 ~R D475 is as defined in the formula (D43B) above.

[0271] In one embodiment, R D471 ~R D475 At least one of the a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ), or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0272] In one embodiment, R D472 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R D471 and R D473 ~R D475 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ), or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0273] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43C): [ka] (In formula (D43C), R D481 and R D482 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R D483 ~R D486 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0274] In one embodiment, the compound represented by formula (D43) is a compound represented by formula (D43C'): [ka] (In formula (D43C'), R D483 ~R D486 is as defined in the formula (D43C) above.

[0275] In one embodiment, R D481 ~R D486 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 50 ring carbon atoms.

[0276] In one embodiment, R D481 ~R D486 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0277] In one embodiment, the compound represented by formula (D41) is a compound represented by formula (D44): [ka] (In formula (D44), X D401 is O or S. R D401B is R D487 and R D497 R is bonded to one or more selected from the group consisting of D402B is R D489 and R D490 may be bonded to one or more selected from the group consisting of: to form a substituted or unsubstituted heterocycle, or may not be bonded at all. R that does not form the substituted or unsubstituted heterocycle D401B and R D402B are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R D487 ~R D497 One or more pairs of two or more adjacent groups among these may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not be bonded to each other. R that does not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted saturated or unsaturated ring D487 ~R D497 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R901 ~R 907 is as defined in the above formula (1).

[0278] In one embodiment, R D401B and R D402B 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 50 ring carbon atoms.

[0279] In one embodiment, R D487 ~R D497 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 50 ring carbon atoms.

[0280] The compound represented by formula (D41) is prepared by first connecting the ring a, ring b, and ring c to a linking group (NR D401 and groups containing NR D402 An intermediate is produced by linking the rings a, b, and c with a linking group (a group containing B) (reaction 1), and the final product is produced by linking the rings a, b, and c with a linking group (a group containing B) (reaction 2). In reaction 1, an amination reaction such as the Bachburt-Hartwig reaction can be applied. In reaction 2, a tandem hetero-Friedel-Crafts reaction can be applied.

[0281] Specific examples of the compound represented by formula (D41) are listed below, but these are merely illustrative, and the compound represented by formula (D41) is not limited to the following specific examples.

[0282] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0283] In addition to the compounds represented by the above-mentioned formula (D11), formula (D21), formula (D31), or formula (D41), the light-emitting layer can also use, for example, the compounds shown below.

[0284] [ka]

[0285] In one embodiment, the light-emitting layer contains a compound represented by formula (D31) or (D41) above.

[0286] In one embodiment, the organic EL device according to one aspect of the present invention has a hole transporting region between the anode and the light-emitting layer.

[0287] In one embodiment, the organic EL device according to one aspect of the present invention has an electron transporting region between the cathode and the light-emitting layer.

[0288] The schematic configuration of an organic EL device according to one embodiment of the present invention will be described with reference to FIG. In one embodiment, an organic EL device 1 according to one aspect of the present invention includes a substrate 2, an anode 3, an emitting layer 5, a cathode 10, a hole-transporting region 4 located between the anode 3 and the emitting layer 5, and an electron-transporting region 6 located between the emitting layer 5 and the cathode 10.

[0289] A typical element configuration of the organic EL element of the present invention is exemplified by a structure in which the following structures are laminated on a substrate. (1) Anode / 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.)

[0290] The hole transport region is a general term for one or more layers disposed between the anode and the light-emitting layer. The hole transport region is composed of, for example, layers called an electron blocking layer, a hole transport layer, and a hole injection layer, which will be described later, from the light-emitting layer side. The hole transport region may have a laminate structure including all of these layers, or may have a layer structure including only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers. For example, two types of hole transport layers with different compositions may be laminated. Each layer may be formed using only one type of material, or may be formed using two or more types of materials in combination.

[0291] The electron transport region is a general term for one or more layers disposed between the cathode and the light-emitting layer. The electron transport region is composed of, for example, layers called a hole-blocking layer, an exciton-blocking layer, an electron-transporting layer, and an electron-injection layer, which will be described later, from the light-emitting layer side. The electron transport region may have a laminate structure including all of these layers, or may have a layer structure including only some of these layers. Furthermore, two or more types of layers may be used for each of the above layers. For example, two types of electron-transporting layers with different compositions may be laminated. Each layer may be formed using only one type of material, or may be formed using two or more types of materials in combination.

[0292] Hereinafter, members that can be used in the organic EL device according to one embodiment of the present invention, and materials that constitute each layer will be described.

[0293] (Emitting layer) In one embodiment, the light-emitting layer includes a compound according to an aspect of the present invention (the first compound, the second compound, or the third compound).

[0294] In one embodiment, the first layer contains a compound according to one aspect of the present invention and a compound represented by any one of the formulae (D11) to (D41). In one embodiment, the first layer contains a compound according to one aspect of the present invention as a host material (sometimes referred to as a matrix material). In one embodiment, the first layer further comprises a dopant material. In one embodiment, the first layer contains a compound represented by any one of the formulae (D11) to (D41) as a dopant material (which may also be referred to as a guest material, an emitter, or a light-emitting material).

[0295] In one embodiment, the first layer includes more than 1.1 wt. %, 1.2 wt. % or more, or 1.5 wt. % or more of the dopant material based on the total weight of the first layer. In one embodiment, the first layer contains no more than 10 wt. %, no more than 7 wt. %, or no more than 5 wt. % of the dopant material based on the total weight of the first layer.

[0296] In one embodiment, the first layer contains at least 60%, at least 70%, at least 80%, at least 90%, or at least 95% by weight of the host material based on the total weight of the first layer. In one embodiment, the first layer contains the host material in an amount of 99% by weight or less of the total weight of the first layer.

[0297] The first layer may contain materials other than the host material and the dopant material.

[0298] In one embodiment, the first layer consists of or consists essentially of a host material and a dopant material, which may contain unavoidable impurities. In one embodiment, the first layer is at least 80% by weight, at least 85% by weight, at least 90% by weight, at least 95% by weight, at least 99% by weight, at least 99.5% by weight, at least 99.9% by weight, at least 99.99% by weight, or at least 100% by weight of the host material and the dopant material.

[0299] The first layer may contain only one type of host material or two or more types of dopant materials.

[0300] The light-emitting layer is a layer containing a highly light-emitting substance, and various materials can be used. For example, as the highly light-emitting substance, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used, in addition to the compounds represented by any of the above formulas (D11) to (D41). 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 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 fluorescent materials that can be used in the light-emitting layer include aromatic amine derivatives. Examples of red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives. Examples of blue phosphorescent materials that can be used in the light-emitting layer include metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples of green phosphorescent materials that can be used in the light-emitting layer include iridium complexes. Examples of red phosphorescent materials that can be used in the light-emitting layer include metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes.

[0301] The light-emitting layer may have a structure in which the highly light-emitting substance (guest material) described above is dispersed in another substance (host material). As a substance for dispersing the highly light-emitting substance, various substances can be used in addition to the above-described materials used in the present invention (compounds according to one embodiment of the present invention). It is preferable to use a substance having a higher lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the highly light-emitting substance. Examples of substances (host materials) for dispersing highly luminescent substances include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 4) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives. In addition, a delayed fluorescent (thermally activated delayed fluorescent) compound can also be used as the host material. It is also preferable that the light-emitting layer contains the material used in the present invention described above and a delayed fluorescent host compound. The light-emitting layer may or may not contain the above-mentioned other substances in addition to the materials used in the present invention described above.

[0302] (Second layer) The second layer contains at least one compound different from that of the first layer. In one embodiment, the second layer contains a host material (second host material). The host material may be any of the substances listed as the host material (first host material) of the first layer. In one embodiment, the second host material is a different compound than the first host material contained in the first layer. In addition, a delayed fluorescent (thermally activated delayed fluorescent) compound can also be used as the host material. The light-emitting layer can also contain the compound according to one embodiment of the present invention described above and a delayed fluorescent host compound.

[0303] In one embodiment, the second layer further includes a dopant material (second dopant material), which may be any of the dopant materials (first dopant materials) listed above for the first layer. In one embodiment, the second dopant material is a compound represented by any of the above formulas (D11) to (D41). In one embodiment, the second dopant material is a different compound than the first dopant material. In one embodiment, the second dopant material is the same compound as the first dopant material.

[0304] In one embodiment, the second layer contains more than 1.1 wt. %, 1.2 wt. % or more, or 1.5 wt. % or more of the dopant material based on the total weight of the second layer. In one embodiment, the second layer contains no more than 10 wt. %, no more than 7 wt. %, or no more than 5 wt. % of the dopant material based on the total weight of the second layer.

[0305] In one embodiment, the second layer comprises 60% by weight or more, 70% by weight or more, 80% by weight or more, 90% by weight or more, or 95% by weight or more of the host material based on the total weight of the second layer. In one embodiment, the second layer contains the host material in an amount of 99% by weight or less of the total weight of the second layer.

[0306] The second layer may contain materials other than the host material and the dopant material.

[0307] In one embodiment, the second layer consists of or consists essentially of a host material and a dopant material, which may contain unavoidable impurities. In one embodiment, the second layer is at least 80% by weight, at least 85% by weight, at least 90% by weight, at least 95% by weight, at least 99% by weight, at least 99.5% by weight, at least 99.9% by weight, at least 99.99% by weight, or at least 100% by weight of the host material and the dopant material.

[0308] The second layer may contain only one type of host material or two or more types of dopant materials.

[0309] The second layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer. In one embodiment, the second layer is a fluorescent light-emitting layer.

[0310] (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 thereof include plastic substrates made of polycarbonate or polyvinyl chloride.

[0311] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metal materials (e.g., titanium nitride).

[0312] (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, an aromatic amine compound, or a polymer compound (such as an oligomer, dendrimer, or polymer).

[0313] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, and the like can be used for the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, other substances may be used as long as they have a higher hole transport property than electron transport property. The layer containing the substance with high hole transport properties may be a single layer or a stack of two or more layers made of the above substances.

[0314] (electron blocking layer, hole blocking layer, exciton blocking layer) An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that has the function of preventing electrons from leaking from the light-emitting layer to the hole transport layer. The hole blocking layer is a layer that has the function of preventing holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer is a layer that has the function of preventing excitons generated in the light-emitting layer from diffusing to adjacent layers and confining the excitons within the light-emitting layer.

[0315] (electron transport layer) The electron transport layer is a layer containing a substance with high electron transport properties, and examples of the electron transport layer include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds.

[0316] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. The electron injection layer may contain metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and 8-hydroxyquinolinolato-lithium (Liq), lithium oxide (LiO x ), alkaline metals such as alkaline earth metals, or compounds thereof can be used.

[0317] (cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0318] In the organic EL device according to one embodiment of the present invention, the thickness of each layer is not particularly limited, but in general, in order to suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency, the thickness is preferably in the range of several nm to 1 μm.

[0319] In the organic EL device according to one embodiment of the present invention, the method for 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 in a solvent, spin coating, casting, bar coating, or roll coating.

[0320] [Electronic equipment] An electronic device according to an aspect of the present invention is characterized by including 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, personal computers, and light-emitting devices such as lighting or vehicle lamps. [Example]

[0321] <Compound> The compounds according to one embodiment of the present invention used in the production of the organic EL devices of Examples 1 to 28 are shown below. [ka] [ka] [ka] [ka] [ka] [ka]

[0322] The comparative compounds used in the production of the organic EL devices of Comparative Examples 1 to 9 are shown below. [ka] [ka]

[0323] The structures of other compounds used in the production of the organic EL devices of Examples 1 to 28 and Comparative Examples 1 to 9 are shown below. [ka] [ka]

[0324] 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, and compound HI-1 was first deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 5 nm. On the hole injection layer, the compound HT-1 was vapor-deposited to form a first hole transport layer having a thickness of 80 nm. On the first hole transport layer, the compound EB-1 was vapor-deposited to form a second hole transport layer having a thickness of 10 nm. On the second hole transport layer, compound BH1-1 (host material) and compound BD-1 (dopant material) were co-deposited so that the proportion of compound BD-1 was 2 mass %, to form a first light-emitting layer with a thickness of 5 nm. On the first emitting layer, compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited so that the proportion of compound BD-1 was 2 mass %, to form a second emitting layer with a thickness of 20 nm. On the second light-emitting layer, the compound aET-1 was vapor-deposited to form a first electron-transporting layer having a thickness of 10 nm. On the first electron transport layer, the compound bET-1 was vapor-deposited to form a second electron transport layer having a thickness of 15 nm. LiF was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm.

[0325] The device configuration of the organic EL device of Example 1 is shown in outline below. ITO(130) / HI-1(5) / HT-1(80) / EB-1(10) / BH1-1:BD-1(5:2%) / BH-2:BD-1(20:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm), and the percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the layer.

[0326] <Evaluation of organic EL elements> The fabricated organic EL devices were evaluated as follows, and the results are shown in Table 1. Drive voltage The initial characteristics of the organic EL element were measured at room temperature with a constant DC (direct current) current of 10 mA / cm 2 Measured with driving. External quantum efficiency (EQE) Current density is 10mA / cm 2 A voltage was applied to the organic EL element so that the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). ·Element life At room temperature, the current density is 50mA / cm 2 A voltage was applied to the organic EL element so that the voltage was 95% of the initial voltage, and the time (LT95 (unit: h)) until the brightness reached 95% of the initial brightness was measured.

[0327] Examples 2 to 4 Organic EL devices were produced and evaluated in the same manner as in Example 1, except that in forming the first light-emitting layer, the compound shown in Table 1 was used instead of compound BH1-1. The results are shown in Table 1.

[0328] Comparative Example 1 Organic EL devices were produced and evaluated in the same manner as in Example 1, except that in forming the first light-emitting layer, the compound shown in Table 1 was used instead of compound BH1-1. The results are shown in Table 1.

[0329] [Table 1]

[0330] Example 6 <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, and compound HI-1 was first deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 5 nm. On the hole injection layer, the compound HT-2 was vapor-deposited to form a first hole transport layer having a thickness of 80 nm. On the first hole transport layer, the compound EB-2 was vapor-deposited to form a second hole transport layer having a thickness of 10 nm. On the second hole transport layer, compound BH1-6 (host material) and compound BD-1 (dopant material) were co-deposited so that the proportion of compound BD-1 was 2 mass %, to form a first light-emitting layer with a thickness of 5 nm. On the first emitting layer, compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited so that the proportion of compound BD-1 was 2 mass %, to form a second emitting layer with a thickness of 20 nm. On the second light-emitting layer, the compound aET-1 was vapor-deposited to form a first electron-transporting layer having a thickness of 10 nm. On the first electron transport layer, the compound bET-1 was vapor-deposited to form a second electron transport layer having a thickness of 15 nm. LiF was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm.

[0331] The device configuration of the organic EL device of Example 6 is shown in outline below. ITO(130) / HI-1(5) / HT-2(80) / EB-2(10) / BH1-6:BD-1(5:2%) / BH-2:BD-1(20:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm), and the percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the layer.

[0332] <Evaluation of organic EL elements> The produced organic EL device was evaluated in the same manner as in Example 1. The results are shown in Table 2.

[0333] Examples 7 to 16 Organic EL devices were produced and evaluated in the same manner as in Example 6, except that in forming the first light-emitting layer, the compounds shown in Table 2 were used instead of compound BH1-6. The results are shown in Table 2.

[0334] Comparative Examples 2 to 4 Organic EL devices were produced and evaluated in the same manner as in Example 6, except that in forming the first light-emitting layer, the compounds shown in Table 2 were used instead of compound BH1-6. The results are shown in Table 2.

[0335] [Table 2]

[0336] Example 17 <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, and compound HI-1 was first deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 5 nm. On the hole injection layer, the compound HT-1 was vapor-deposited to form a first hole transport layer having a thickness of 80 nm. On the first hole transport layer, the compound EB-1 was vapor-deposited to form a second hole transport layer having a thickness of 10 nm. On the second hole transport layer, compound BH1-11 (host material) and compound BD-1 (dopant material) were co-deposited so that the proportion of compound BD-1 was 2 mass %, to form a first light-emitting layer with a thickness of 5 nm. On the first emitting layer, compound BH-3 (host material) and compound BD-1 (dopant material) were co-deposited so that the proportion of compound BD-1 was 2 mass %, to form a second emitting layer with a thickness of 20 nm. On the second light-emitting layer, the compound aET-2 was vapor-deposited to form a first electron-transporting layer having a thickness of 10 nm. On the first electron transport layer, the compound bET-1 was vapor-deposited to form a second electron transport layer having a thickness of 15 nm. LiF was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm.

[0337] The device configuration of the organic EL device of Example 17 is shown in outline below. ITO(130) / HI-1(5) / HT-1(80) / EB-1(10) / BH1-11:BD-1(5:2%) / BH-3:BD-1(20:2%) / aET-2(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm), and the percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the layer.

[0338] <Evaluation of organic EL elements> The produced organic EL device was evaluated in the same manner as in Example 1. The results are shown in Table 3.

[0339] Examples 18 to 22 Organic EL devices were produced and evaluated in the same manner as in Example 17, except that in forming the first light-emitting layer, the compounds shown in Table 3 were used instead of compound BH1-11. The results are shown in Table 3.

[0340] Comparative Example 5 Organic EL devices were produced and evaluated in the same manner as in Example 17, except that in forming the first light-emitting layer, the compounds shown in Table 3 were used instead of compound BH1-11. The results are shown in Table 3.

[0341] [Table 3]

[0342] Example 23 <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, and compound HI-1 was first deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 5 nm. On the hole injection layer, the compound HT-1 was vapor-deposited to form a first hole transport layer having a thickness of 80 nm. On the first hole transport layer, the compound EB-1 was vapor-deposited to form a second hole transport layer having a thickness of 10 nm. On the second hole transport layer, compound BH1-17 (host material) and compound BD-2 (dopant material) were co-deposited so that the proportion of compound BD-2 was 2 mass %, to form a first light-emitting layer with a thickness of 5 nm. On the first emitting layer, compound BH-2 (host material) and compound BD-2 (dopant material) were co-deposited so that the proportion of compound BD-2 was 2 mass %, to form a second emitting layer with a thickness of 20 nm. On the second light-emitting layer, the compound aET-1 was vapor-deposited to form a first electron-transporting layer having a thickness of 10 nm. On the first electron transport layer, the compound bET-1 was vapor-deposited to form a second electron transport layer having a thickness of 15 nm. LiF was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Metallic Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm.

[0343] The device configuration of the organic EL device of Example 23 is shown in outline below. ITO(130) / HI-1(5) / HT-1(80) / EB-1(10) / BH1-17:BD-2(5:2%) / BH-2:BD-2(20:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm), and the percentage numbers in parentheses indicate the proportion (mass %) of the latter compound in the layer.

[0344] <Evaluation of organic EL elements> The produced organic EL device was evaluated in the same manner as in Example 1. The results are shown in Table 4.

[0345] Example 18 Organic EL devices were produced and evaluated in the same manner as in Example 23, except that in forming the first light-emitting layer, the compounds shown in Table 4 were used instead of compound BH1-17. The results are shown in Table 4.

[0346] Comparative Examples 6-7 Organic EL devices were produced and evaluated in the same manner as in Example 23, except that in forming the first light-emitting layer, the compounds shown in Table 4 were used instead of compound BH1-17. The results are shown in Table 4.

[0347] [Table 4]

[0348] Examples 25 to 28 Organic EL devices were produced and evaluated in the same manner as in Example 1, except that in forming the first light-emitting layer, the compounds shown in Table 5 were used instead of compound BH1-1. The results are shown in Table 5.

[0349] Comparative Examples 8-9 Organic EL devices were produced and evaluated in the same manner as in Example 1, except that in forming the first light-emitting layer, the compounds shown in Table 5 were used instead of compound BH1-1. The results are shown in Table 5.

[0350] [Table 5]

[0351] <Synthesis of Compounds> (Synthesis Example 1) Synthesis of Compound BH1-1 Compound BH1-1 was synthesized according to the following synthetic route. [ka]

[0352] Under an argon atmosphere, 4,4,5,5-tetramethyl-2-[( 2 H 11 A mixture of 3.65 g (10.0 mmol) of [(tetraphen-7-yl)]-1,3,2-dioxaborolane (Intermediate A), 4.32 g (11.0 mmol) of 7-phenyldibenzo[b,d]furan-1-yl trifluoromethanesulfonate (Intermediate B), 0.183 g (0.20 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.328 g (0.80 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), 12.5 mL of 2M aqueous sodium carbonate, and 100 mL of 1,4-dioxane was refluxed at boiling point for 6 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 4.11 g of compound BH1-1 as a white solid. Mass spectrometry analysis showed that the obtained product was compound BH1-1, with a molecular weight of 481.64 and an m / z value of 482.

[0353] (Synthesis Examples 2 to 19) Synthesis of Compounds BH1-2 to BH1-10 and BH1-19 to BH1-27 The compounds were synthesized in the same manner as in Synthesis Example 1, except that the compounds in Synthesis Example 1 were changed to the compounds shown in Tables 6 to 9, respectively. [Table 6] [Table 7] [Table 8] [Table 9]

[0354] (Synthesis Example 20) Synthesis of Compound BH1-11 Compound BH1-11 was synthesized according to the following synthetic route. [ka]

[0355] Under an argon atmosphere, a mixture of 7.67 g (20.0 mmol) of intermediate M-1, 8.15 g (22.0 mmol) of intermediate M-2, 0.364 g (0.40 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.629 g (1.60 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (DavePhos), 19.5 g of cesium carbonate, 160 mL of 1,4-dioxane, and 27 mL of water was refluxed at the boiling point for 8 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.56 g of compound BH1-11 as a white solid (60% yield). Mass spectrometry analysis showed that the obtained product was compound BH1-11, with an m / z value of 547 for a molecular weight of 546.67.

[0356] (Synthesis Examples 21 to 28) Synthesis of Compounds BH1-12 to BH1-18 and BH1-28 The compounds were synthesized in the same manner as in Synthesis Example 20, except that the compounds in Synthesis Example 20 were changed to the compounds shown in Tables 10 and 11, respectively. [Table 10] [Table 11]

[0357] (Intermediate Synthesis Example 1) Synthesis of Intermediate M-3 Intermediate M-3 was synthesized according to the following synthesis route. [ka]

[0358] (Intermediate Synthesis Example 1-1) Synthesis of Intermediate M-3B Under an argon atmosphere, a mixture of 3.07 g (10.0 mmol) of intermediate M-3A, 2.12 g (10.0 mmol) of dibenzofuran-2-ylboronic acid, 0.163 g (0.20 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 15 mL of 2 M aqueous sodium carbonate, and 50 mL of DME was stirred at 70 °C for 6 hours. After cooling to room temperature, the precipitated solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to obtain 3.23 g of a white solid. The yield was 82%.

[0359] (Intermediate Synthesis Example 1-2) Synthesis of Intermediate M-3 Under an argon atmosphere, a mixture of 3.16 g (7.00 mmol) of intermediate M-3A, 1.31 g (7.35 mmol) of N-bromosuccinimide, and 18 mL of dichloroethane was stirred at 70°C for 48 hours. After the reaction mixture was cooled to room temperature, the precipitated solid was collected by filtration. The obtained solid was purified by silica gel column chromatography to obtain 2.32 g of a white solid. The yield was 70%.

[0360] (Intermediate Synthesis Example 2) Synthesis of Intermediate M-4 Intermediate Synthesis Examples 2-1 and 2-2 were synthesized in the same manner as in Intermediate Synthesis Example 1, except that the compounds in Intermediate Synthesis Examples 1-1 and 1-2 were changed to the compounds shown in Tables 12 and 13, respectively.

[0361] (Intermediate Synthesis Example 3) Synthesis of Intermediate M-5 Intermediate Synthesis Examples 3-1 and 3-2 were synthesized in the same manner as in Intermediate Synthesis Example 1, except that the compounds in Intermediate Synthesis Examples 1-1 and 1-2 were changed to the compounds shown in Tables 12 and 13, respectively. [Table 12] [Table 13]

Claims

1. A compound represented by formula (3): 【Chemistry 1】 [In formula (3), R ３０１ ~R ３１２ At least one of the above is a group represented by the following formula (31): R which is not a group represented by the formula (31) ３０１ ~R ３１２ are each independently a hydrogen atom or a substituent R. However, R ３０７ is a group represented by the formula (31), R ３０１ ~R ３１２ are each independently a hydrogen atom or a substituent Q. R ３０１ ~R ３１２ One or more of the sets of two or more adjacent ones of the groups are not bonded to each other. 【Chemistry 2】 (In formula (31), L ３０１ teeth, single bond, a substituted or unsubstituted phenylene group, or It is a substituted or unsubstituted naphthalenediyl group. n301 is an integer from 0 to 3. If n301 is 0, then (L ３０１ ) ｎ３０１ is a single bond. When n301 is 2 or more, L ３０１ are connected in series with each other. When n301 is 2 or more, L ３０１ may be the same as or different from each other. Ar ３０１ represents an unsubstituted aryl group having 6 to 15 ring carbon atoms. n302 is an integer from 1 to 3. When n302 is 2 or more, 2 or more Ar ３０１ may be the same as or different from each other. X ３０１ is C(R ３２９ ) (R ３３０ ) or O. R ３２１ ~R 330 is L ３０１ represents a single bond that connects to R that does not represent a single bond ３２１ ~R ３２８ Of these, n302 are Ar ３０１ represents a single bond that connects to R that does not represent a single bond ３２１ to R 330 are each independently a hydrogen atom or a substituent R. R ３２９ and R ３３０ pairs are disjoint.) The substituent R is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ )、 -O-(R ９０４ )、 -S-(R ９０５ )、 -N(R ９０６ )(R ９０７ )、 Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R ９０１ ~R ９０７ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R ９０１ ~R ９０７ When there are two or more R ９０１ ~R ９０７ may be the same or different. When two or more substituents R are present, the two or more substituents R may be the same or different. The substituent Q 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 )、 a halogen atom, a cyano group, a nitro group, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R ９０１ ~R ９０７ is as defined for the substituent R. When two or more substituents Q are present, the two or more substituents Q may be the same or different.

2. L ３０１ The compound according to claim 1 , wherein is a single bond or a substituted or unsubstituted phenylene group.

3. R is a hydrogen atom ３０１ ~R ３１２ , R is the substituent R ３０１ ~R ３１２ a hydrogen atom possessed by R is a substituent Q ３０１ ~R ３１２ a hydrogen atom possessed by L ３０１ a hydrogen atom possessed by R is a hydrogen atom ３２１ ~R 330, Ar ３０１ and a hydrogen atom in R is the substituent R ３２９ ~R 330 has a hydrogen atom 3. The compound according to claim 1, wherein one or more hydrogen atoms selected from the group consisting of are deuterium atoms.

4. R is a hydrogen atom ３０１ ~R ３１２ , R is the substituent R ３０１ ~R ３１２ a hydrogen atom possessed by R is a substituent Q ３０１ ~R ３１２ a hydrogen atom possessed by wherein one or more hydrogen atoms selected from the group consisting of are deuterium atoms; L ３０１ a hydrogen atom possessed by R is a hydrogen atom ３２１ ~R 330, Ar ３０１ and a hydrogen atom in R is the substituent R ３２９ The compound according to claim 1 or 2, wherein the hydrogen atoms possessed by R 330 to R 330 are proton atoms.

5. R ３０４ , R ３０６ , R ３０７ , R ３１１ , and R ３１２ The compound according to claim 1 or 2, wherein at least one of the following is a group represented by formula (31):

6. R ３０７ and R ３１２ The compound according to claim 1 or 2, wherein at least one of the following is a group represented by formula (31):

7. R ３２１ ~R ３２４ One of them is L ３０１ 3. The compound of claim 1 or 2, wherein R represents a single bond connecting to

8. R ３２３ and R ３２４ One of them is L ３０１ 3. The compound of claim 1 or 2, wherein R represents a single bond connecting to

9. The compound according to claim 1, wherein the compound represented by formula (3) is a compound represented by any one of the following formulas (3-1) to (3-5): 【Transformation 3】 【Chemistry 4】 [In formulas (3-1) to (3-5), R ３０１ ~R ３１２ , L ３０１ , n301, n302, Ar ３０１ , X ３０１ , and R ３２１ ~R ３２８ is as defined in the above formula (3).

10. The compound represented by formula (3) is a compound represented by any one of the following formulas (3-11) to (3-21), (3-31), (3-41) to (3-46), and (3-51) to (3-52): The compound according to claim 1. 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 [In formulas (3-11) to (3-21), (3-31), (3-41) to (3-46), and (3-51) to (3-52), R ３０１ ~R ３１２ , L ３０１ , n301, Ar ３０１ , X ３０１ , and R ３２１ ~R ３２８ is as defined in the above formula (3).

11. The compound according to claim 1 or 2, which is a material for an organic electroluminescence device.

12. A cathode; an anode; one or more organic layers disposed between the cathode and the anode; and At least one of the organic layers contains the compound according to claim 1 or 2. Organic electroluminescent element.

13. 13. The organic electroluminescence device according to claim 12, comprising an anode, an emitting layer, and a cathode in this order, wherein at least one organic layer in the emitting layer contains the compound.

14. 14. The organic electroluminescence device according to claim 13, wherein the light-emitting layer comprises, from the anode side, a first layer and a second layer, and the first layer comprises the compound.

15. 14. The organic electroluminescence device according to claim 13, wherein the light-emitting layer further contains a compound represented by any one of the following formulas (D11) to (D41): 【Chemistry 12】 [In formula (D11), Each of the three Zs independently represents CR ａ or a nitrogen atom. Ring A1 and ring A2 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. R ａ If there are multiple R ａ One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. nD11 and nD12 are each independently 0, 1, 2, 3, or 4. R ｂ If there are multiple R ｂ One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. R ｃ If there are multiple R ｃ One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Do not bond with each other. R that does not form the single ring or the fused ring ａ , R ｂ , and R ｃ are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ )、 -O-(R ９０４ )、 -S-(R ９０５ )、 -N(R ９０６ )(R ９０７ )、 Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R ９０１ ~R ９０７ is as defined in the above formula (3). In formula (D21), R Ｄ２０１ and R Ｄ２０２ , R Ｄ２０２ and R Ｄ２０３ , and R Ｄ２０３ and R Ｄ２０４ At least one pair of these bonds are bonded to each other to form a divalent group represented by the following formula (D22): R Ｄ２０５ and R Ｄ２０６ , R Ｄ２０６ and R Ｄ２０７ , and R Ｄ２０７ and R Ｄ２０８ At least one pair of these bonds are bonded to each other to form a divalent group represented by the following formula (D23): 【Chemistry 13】 R Ｄ２１１ ~R Ｄ２１４ and R which does not form a divalent group represented by formula (D22). Ｄ２０１ ~R Ｄ２０４ At least one of the groups represented by the following formula (D24) is a monovalent group. R Ｄ２２１ ~R Ｄ２２４ and R which does not form a divalent group represented by formula (D23). Ｄ２０５ ~R Ｄ２０８ At least one of the groups represented by the following formula (D24) is a monovalent group. X Ｄ２ is an oxygen atom, a sulfur atom, or NR Ｄ２０９ is. R which does not form a divalent group represented by the formula (D22) or the formula (D23) and is not a monovalent group represented by the formula (D24) Ｄ２０１ ~R Ｄ２０８ , R which is not a monovalent group represented by formula (D24) Ｄ２１１ ~R Ｄ２１４ and R Ｄ２２１ ~R Ｄ２２４ , and R Ｄ２０９ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ )、 -O-(R ９０４ )、 -S-(R ９０５ )、 -N(R ９０６ )(R ９０７ )、 Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 【Chemistry 14】 (In formula (D24), Ar Ｄ２０１ and Ar Ｄ２０２ are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. L Ｄ２０１ ~L Ｄ２０３ are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or It is a divalent linking group formed by bonding two to four groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 30 ring carbon atoms and substituted or unsubstituted divalent heterocyclic groups having 5 to 30 ring atoms. * indicates the bonding position to the ring structure represented by formula (D21) or the group represented by formula (D22) or formula (D23). R ９０１ ~R ９０７ is as defined in the above formula (3). In formula (D31), R Ｄ３０１ ~R Ｄ３０７ and R Ｄ３１１ ~R Ｄ３１７ at least one pair of adjacent two or more of these may be bonded to each other to form a substituted or unsubstituted monocycle, may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other. R that does not form the single ring or the fused ring Ｄ３０１ ~R Ｄ３０７ and R Ｄ３１１ ~R Ｄ３１７ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ )、 -O-(R ９０４ )、 -S-(R ９０５ )、 -N(R ９０６ )(R ９０７ )、 Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R Ｄ３２１ and R Ｄ３２２ are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ )、 -O-(R ９０４ )、 -S-(R ９０５ )、 -N(R ９０６ )(R ９０７ )、 Halogen atoms, cyano groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. R ９０１ ~R ９０７ is as defined in the above formula (3). In formula (D41), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. R Ｄ４０１ and R Ｄ４０２ each independently bonds to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or does not bond to the ring a, ring b, or ring c. R that does not form a heterocyclic ring Ｄ４０１ and R Ｄ４０２ are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.]

16. 14. The organic electroluminescence device according to claim 13, further comprising a hole transporting region between the anode and the light emitting layer.

17. 14. The organic electroluminescence device according to claim 13, further comprising an electron transporting region between the cathode and the light-emitting layer.

18. An electronic device comprising the organic electroluminescence device according to claim 12.

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