Compound, organic electroluminescent element, and electronic device

Abstract

An organic electroluminescent element (1B) comprises an anode (3), a cathode (4), and a light-emitting region (5B) disposed between the anode (3) and the cathode (4). The light-emitting region (5B) includes a first light-emitting layer (51) and a second light-emitting layer (52). The first light-emitting layer (51) contains a first compound represented by general formula (100A), and the second light-emitting layer (52) contains a second compound. (At least any one of R101 to R112 in general formula (100A) and L101 and Ar101 in general formula (100B) has at least one deuterium atom, and if only L101 has a deuterium atom, the deuterium atom bonds to a ring that directly bonds to a benz[a]anthracene ring in general formula (100A) from among the rings constituting L101.)

Description

Compound, organic electroluminescent element, and electronic device

[0001] The present invention relates to a compound, an organic electroluminescence element, and an electronic device.

[0002] Organic electroluminescence elements (hereinafter sometimes referred to as "organic EL elements") are applied to full-color displays such as mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. The injected holes and electrons then recombine in the light-emitting layer to form excitons. According to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons at a rate of 75%. In order to improve the performance of organic EL elements, various studies have been conducted on compounds used in organic EL elements (see, for example, Patent Documents 1 and 2). Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0003] International Publication No. 2021 / 132535 ​​Special Publication No. 2013-509363

[0004] An object of the present invention is to provide a compound capable of improving the lifetime of an organic electroluminescent element, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element. Another object of the present invention is to provide an organic electroluminescent element having an improved lifetime and an electronic device equipped with the organic electroluminescent element.

[0005] According to one aspect of the present invention, there is provided a compound represented by the following general formula (1A):

[0006] (In the general formula (1A), R ４ ~R ８ and R １０ ~R １２ one of R is a group represented by general formula (1B) １ ~R ３ , R ９and R other than the group represented by general formula (1B). ４ ~R ８ and R １０ ~R １２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ８０１ , and R ８０２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, and in the general formula (1B), n1 is 0 or an integer of 1 or more, and when n1 is an integer of 1 or more, L １ represents an unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, provided that the unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring, and １ When there are two or more, there are two or more L １ are the same or different from each other, Ar １ represents an aryl group having four or more substituted or unsubstituted rings fused thereto, or a heterocyclic group having four or more substituted or unsubstituted rings fused thereto, * represents the bonding position with the benz[a]anthracene ring in the general formula (1A), provided that R １ ~R １２ and L in the general formula (1B). １ and Ar １ At least one of the groups has at least one deuterium atom, and L １ When only L has a deuterium atom, １ Among the rings constituting the formula (1A), a deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in the formula (1A).

[0007] According to one aspect of the present invention, there is provided an organic electroluminescence device containing the compound according to one aspect of the present invention.

[0008] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, and an emitting region disposed between the anode and the cathode, the emitting region including a first emitting layer and a second emitting layer, the first emitting layer containing a first compound represented by the following general formula (100A), and the second emitting layer containing a second compound:

[0009]

[0010] (In the general formula (100A), R １０１ ~R １１２ one of the R is a group represented by the general formula (100B), and R other than the group represented by the general formula (100B) １０１ ~R １１２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ８０１ , and R ８０２are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, and in the general formula (100B), n101 is 0 or an integer of 1 or more, and when n101 is an integer of 1 or more, L １０１ represents an unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, provided that the unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring, and １０１ When there are two or more, there are two or more L １０１ are the same or different from each other, Ar １０１ represents an aryl group in which three or more substituted or unsubstituted rings are fused, or a heterocyclic group in which three or more substituted or unsubstituted rings are fused, * represents the bonding position to the benz[a]anthracene ring in general formula (100A), provided that R １０１~R １１２ and L in the general formula (100B). １０１ and Ar １０１ At least one of the groups has at least one deuterium atom, and L １０１ When only L has a deuterium atom, １０１ A deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in general formula (100A) among the rings that constitute the formula (100A).

[0011] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention.

[0012] According to one embodiment of the present invention, it is possible to provide a compound capable of improving the lifetime of an organic electroluminescence element, an organic electroluminescence element including the compound, and an electronic device equipped with the organic electroluminescence element. Also, according to another embodiment of the present invention, it is possible to provide an organic electroluminescence element having an improved lifetime and an electronic device equipped with the organic electroluminescence element.

[0013] 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to an embodiment of the present invention, and FIG. 2 is a diagram showing a schematic configuration of another example of an organic electroluminescence element according to an embodiment of the present invention.

[0014] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0015] In this specification, in a chemical structural formula, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0016] 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. 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 a benzene ring substituted with an alkyl group is 6. Furthermore, when the 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.

[0017] 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 is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. 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.

[0018] 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" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0019] In this specification, the "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having number of atoms XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0020] In this specification, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protist atom, a deuterium atom, or a tritium atom. Furthermore, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0021] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0022] The number of ring carbon atoms of an "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring atoms of an "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms of an "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring carbon atoms of an "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. Unless otherwise specified herein, the number of ring carbon atoms of an "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18. Unless otherwise specified herein, the number of ring atoms of an "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18. Unless otherwise specified herein, the number of carbon atoms of an "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0023] "Substituted or Unsubstituted Aryl Group" Specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl group" described herein include the following unsubstituted aryl group (Specific Example Group G1A) and substituted aryl group (Specific Example Group G1B). (Here, an unsubstituted aryl group refers to a case where a "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where a "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 substituents. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with substituents in the "unsubstituted aryl group" of the following Specific Example Group G1A, and examples of the substituted aryl group of the following Specific Example Group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl groups" of the following specific example group G1B is further replaced with a substituent.

[0024] Unsubstituted aryl groups (specific example group G1A): 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 benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, A 9,9'-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0025]

[0026]

[0027] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0028] "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 group" described herein is a monocyclic group or a fused ring group. The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described herein include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, an unsubstituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to when a "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". A "substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with substituents. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of an "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of substituted heterocyclic groups in the following specific example group G2B. The examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification also include groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic groups" of specific example group G2B is further replaced with a substituent.

[0029] 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).

[0030] 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 substituents (specific example group G2B4).

[0031] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolidinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.

[0032] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0033] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0034] 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):

[0035]

[0036]

[0037] 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 CH ２ However, X Ａ and Y Ａ At least one of X is an oxygen atom, a sulfur atom, or NH. Ａ and Y Ａ At least one of the groups is NH or CH ２ In this case, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) may contain any of these NH, CH ２ and monovalent groups obtained by removing one hydrogen atom from the group consisting of:

[0038] 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, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0039] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0040] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0041] 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):

[0042] 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 Ａ One of them is CH ２ and n is 0 or more. The methylene group in the formula (I) is one or more hydrogen atoms selected from the hydrogen atoms of the methylene group in the formula (I).

[0043] "Substituted or Unsubstituted Alkyl Group" 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 term "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the term "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, the term "alkyl group" includes both an "unsubstituted alkyl group" and a "substituted alkyl group." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced with substituents. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (Specific Example Group G3A) in which one or more hydrogen atoms are replaced with substituents, and the examples of the substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in an "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the term "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes groups in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkyl group" of specific example group G3B is further replaced with a substituent.

[0044] Unsubstituted alkyl groups (specific example group G3A): a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group.

[0045] Substituted alkyl groups (specific example group G3B): a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.

[0046] "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, an unsubstituted alkenyl group refers to a case where a "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and a "substituted alkenyl group" refers to a case where a "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply refers to both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with substituents. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and 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 which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted alkenyl groups" of specific example group G4B is further replaced with a substituent.

[0047] Unsubstituted alkenyl groups (specific example group G4A): a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.

[0048] Substituted alkenyl groups (specific example group G4B): a 1,3-butadienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 1,2-dimethylallyl group.

[0049] - "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 group (specific example group G5A). (Here, an unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, the term "alkynyl group" includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (specific example group G5A) have been replaced with a substituent.

[0050] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group

[0051] "Substituted or Unsubstituted Cycloalkyl Group" 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 term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply refers to both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced with substituents. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (Specific Example Group G6A) in which one or more hydrogen atoms are replaced with substituents, 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 groups" described in this specification also include groups in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl groups" of specific example group G6B are replaced with substituents, and groups in which a hydrogen atom of a substituent in the "substituted cycloalkyl groups" of specific example group G6B is further replaced with a substituent.

[0052] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.

[0053] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0054] -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 the formula (G1) include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) may be the same or different. - Multiple G2 in Si(G1)(G2)(G2) are the same as or different from each other. - Multiple G1 in Si(G1)(G1)(G2) are the same as or different from each other. - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other. - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other. - Multiple G6 in Si(G6)(G6)(G6) are the same as or different from each other.

[0055] ・「-O-(R ９０４ A group represented by —O—(R ９０４ ) (Specific example group G8) includes -O(G1), -O(G2), -O(G3), and -O(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0056] ・"-S-(R ９０５ A group represented by —S—(R ９０５) (Specific example group G9) includes -S(G1), -S(G2), -S(G3), and -S(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0057] ・「-N(R ９０６ ) (R ９０７ A group represented by —N(R ９０６ ) (R ９０７ Specific examples (specific example group G10) of groups represented by the formula (G1) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6). Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. Multiple G1s in -N(G1)(G1) may be the same as or different from one another. Multiple G2s in -N(G2)(G2) may be the same as or different from one another. Multiple G3s in -N(G3)(G3) may be the same as or different from one another. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0058] "Halogen Atom" 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.

[0059] "Substituted or unsubstituted fluoroalkyl group" As used herein, a "substituted or unsubstituted fluoroalkyl group" 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. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. Note that the "substituted fluoroalkyl group" described 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 a 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 have been replaced with fluorine atoms.

[0060] "Substituted or unsubstituted haloalkyl group" As used herein, a "substituted or unsubstituted haloalkyl group" 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. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. Note that the "substituted haloalkyl group" described herein also includes a "substituted haloalkyl group" in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain are further replaced with a substituent, and a "substituted haloalkyl group" in which one or more hydrogen atoms of the substituent are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. A haloalkyl group may also be referred to as a halogenated alkyl group.

[0061] - "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification 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 in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0062] - "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification 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 in this specification, the number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0063] - "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. Unless otherwise specified in this specification, 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.

[0064] - "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. Unless otherwise specified in this specification, 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.

[0065] - "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from one another. Unless otherwise specified in this specification, 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.

[0066] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, 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 in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

[0067] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described in this 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.

[0068] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

[0069] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0070]

[0071] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0072]

[0073] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0074] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0075]

[0076] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0077] 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.

[0078] "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 (specific example group G12) of the "substituted or unsubstituted arylene group" 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.

[0079] "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.

[0080] "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 (specific example group G14) of the "substituted or unsubstituted alkylene group" 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.

[0081] 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).

[0082]

[0083]

[0084] In the general formulae (TEMP-42) to (TEMP-52), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0085]

[0086] In the general formulae (TEMP-53) to (TEMP-62), Q １ ~Q １０ are each independently a hydrogen atom or a substituent. ９ 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 the bonding position.

[0087]

[0088] In the general formulae (TEMP-63) to (TEMP-68), Q １ ~Q ８ are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0089] 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).

[0090]

[0091]

[0092]

[0093] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0094]

[0095]

[0096]

[0097]

[0098] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0099] The above is the explanation of "substituents described in this specification."

[0100] "When bonded to form a ring" In this specification, when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other," it means when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle," when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring," and when "one or more pairs of adjacent groups do not bond to each other." In this specification, the cases when "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocycle" and "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "when bonded to form a ring") will be explained below. An anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be described as an example.

[0101]

[0102] For example, R ９２１~R ９３０ In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the 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 and R ９２９ and R ９２１ It is paired with.

[0103] The above-mentioned "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 and simultaneously form 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).

[0104]

[0105] The case where a "set of two or more adjacent groups" forms a ring includes not only the case where a set of "two" adjacent groups is bonded as in the above example, but also the case where a set of "three or more" adjacent groups is bonded. For example, R ９２１ and R ９２２ and are bonded to each other to form ring Q Ａ and R ９２２ and R ９２３ and are bonded to each other to form ring Q Ｃ and three adjacent (R ９２１ , R ９２２ and R９２３ 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.

[0106]

[0107] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. 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". Ａ , and ring Q Ｃ is a "fused ring". Ａ and Tamaki Q Ｃ That is, Ring Q Ａ and Tamaki Q Ｃ The ring Q in the general formula (TMEP-104) is fused to form a fused ring. Ａ is a benzene ring, then ring Q Ａ The ring Q in the general formula (TMEP-104) is a monocyclic ring. Ａ is a naphthalene ring, then ring Q Ａ is a fused ring.

[0108] The term "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of aromatic hydrocarbon rings 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 aromatic heterocyclic rings include structures in which the aromatic heterocyclic groups given as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. "Forming a ring" means forming a ring only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R ９２１ and R ９２２ and a ring Q formed by bonding together Ａ is R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. ９２１ and R ９２２ Todekan Q Ａ In the case where R ９２１ and the carbon atom of the anthracene skeleton to which R ９２２ When a monocyclic unsaturated ring is formed by the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, R ９２１ and R ９２２ The ring formed by

[0109] Here, unless otherwise specified herein, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In any element (for example, in the case of carbon or nitrogen), a 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 any element other than a carbon element is included, the formed ring is a heterocycle. Unless otherwise specified herein, the "one or more arbitrary elements" constituting the monocycle or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5. Unless otherwise specified herein, of the "monocycle" and the "fused ring," the "monocycle" is preferred. Unless otherwise specified herein, of the "saturated ring" and the "unsaturated ring," the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocycle" 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 element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0110] When the above-mentioned "monocyclic ring" or "fused 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 Herein." 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 Herein." The above is an explanation of the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent two or more rings are bonded to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0111] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, 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 ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ When there are two or more R９０１ are the same or different from each other, R ９０２ When there are two or more R ９０２ are the same or different from each other, R ９０３ When there are two or more R ９０３ are the same or different from each other, R ９０４ When there are two or more R ９０４ are the same or different from each other, R ９０５ When there are two or more R ９０５ are the same or different from each other, R ９０６ When there are two or more R ９０６ are the same or different from each other, R ９０７ When there are two or more R ９０７ are the same or different from each other.

[0112] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[0113] In one embodiment, the substituent in the "substituted or unsubstituted" is a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0114] 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."

[0115] Unless otherwise specified in this specification, adjacent optional substituents may 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 substituents further possessed by the optional substituent are the same as those of the optional substituents described above.

[0116] 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.

[0117] First Embodiment (Compound) The compound according to this embodiment is a compound represented by the following general formula (100A).

[0118]

[0119] (In the general formula (100A), R １０１ ~R １１２ one of the R is a group represented by the general formula (100B), and R other than the group represented by the general formula (100B) １０１ ~R １１２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ８０１ , and R ８０２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, and in the general formula (100B), n101 is 0 or an integer of 1 or more, and when n101 is an integer of 1 or more, L １０１ represents an unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, provided that the unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring, and １０１When there are two or more, there are two or more L １０１ are the same or different from each other, Ar １０１ represents an aryl group in which three or more substituted or unsubstituted rings are fused, or a heterocyclic group in which three or more substituted or unsubstituted rings are fused, * represents the bonding position to the benz[a]anthracene ring in general formula (100A), provided that R １０１ ~R １１２ and L in the general formula (100B). １０１ and Ar １０１ At least one of the groups has at least one deuterium atom, and L １０１ When only L has a deuterium atom, １０１ A deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in general formula (100A) among the rings that constitute the formula (100A).

[0120] In this specification, the term "fused ring" refers to a fused aryl group (for example, a naphthyl group) or a fused heterocyclic group (for example, a carbazolyl group).

[0121] In the compound according to this embodiment, L １０１ When L is an arylene group, the arylene group is an unsubstituted arylene group having 6 to 50 ring carbon atoms that is not a fused ring, or an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused. １０１ In the formula (1A), for example, a divalent group derived from biphenyl and a divalent group derived from terphenyl correspond to an "unsubstituted arylene group having 6 to 50 ring carbon atoms", and a divalent group derived from naphthalene corresponds to an "arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed". １ The same is true for .

[0122] In addition, in the compound according to this embodiment, L １０１ When only L has a deuterium atom, １０１ The "ring directly bonded to the benz[a]anthracene ring in the general formula (100A) among the rings constituting the formula (100A)" is, for example, L１０１ is a biphenyl group represented by the following general formula (101x), and *a corresponds to ring A when it is the bonding position to the benz[a]anthracene ring. １０１ When only L has a deuterium atom, １０１ The phrase "a deuterium atom is bonded to the ring directly bonded to the benz[a]anthracene ring in the general formula (100A) among the rings constituting the formula (100A)" means, for example, L １０１ is a biphenyl group represented by the following general formula (101x), and *a is the bonding position to the benz[a]anthracene ring, this means that a deuterium atom is bonded to at least one of *A1 to *A3 in ring A. １ The same is true for .

[0123]

[0124] (In the general formula (101x), *a is a bonding position to the benz[a]anthracene ring, and *b is a bonding position to Ar １０１ )

[0125] In the compound according to this embodiment, n101 is preferably an integer of 1 or more.

[0126] In the compound according to this embodiment, L １０１ is preferably a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms or a heterocyclic group having 5 to 12 ring atoms, and more preferably a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.

[0127] In the compound according to this embodiment, L １０１ The substituent that is included in is preferably an aryl group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 16 ring atoms, more preferably an aryl group having 6 to 13 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 12 ring atoms, and even more preferably a phenyl group or a naphthyl group.

[0128] In the compound according to this embodiment, L １０１ It is also preferred that is unsubstituted.

[0129] In the compound according to this embodiment, L １０１ is also preferably any of the groups represented by the following general formulae (L101) to (L114): In the examples below, * indicates the bonding position.

[0130]

[0131] In the compound according to this embodiment, n101 is also preferably 0. That is, Ar １０１ It is also preferred that the benz[a]anthracene ring in the general formula (100A) is directly bonded to the benz[a]anthracene ring in the general formula (100A).

[0132] In the compound according to this embodiment, Ar １０１ is also preferably an aryl group in which four or more substituted or unsubstituted rings are condensed, or a heterocyclic group in which four or more substituted or unsubstituted rings are condensed.

[0133] In the compound according to this embodiment, Ar １０１ is also preferably a group represented by the following general formula (1B-1), (1B-2), (1B-3), or (1D).

[0134]

[0135] In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), n1 is 0, 1, 2, or 3, and L when n1 is 1, 2, or 3 １ represents an unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, provided that the unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring, and １ When there are two or more, there are two or more L １ are the same or different from each other, and in the general formula (1B-1), R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), and in general formula (1B-2), R ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４are each independently R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), and in general formula (1B-3), R ５１ ~R ５５ , and R ８１ ~R ８４ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ５１ ~R ５５ , and R ８１ ~R ８４ are each independently R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ * indicates the bonding position to the benz[a]anthracene ring in the general formula (100A), and in the general formula (1D), R ２１ ~R ３０ indicates a bonding position to the benz[a]anthracene ring in general formula (100A), and R in general formula (1D) that is not the bonding position ２１ ~R ３０ at least one pair of adjacent pairs of R in general formula (1D) bond to each other to form a substituted or unsubstituted monocycle, or bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, are not at a bonding position with the benz[a]anthracene ring in general formula (100A), do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ２１ ~R ３０are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and in the groups represented by the general formulae (1B-1), (1B-2), (1B-3), and (1D), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , and R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.)

[0136] In the compound according to this embodiment, Ar １０１ may be a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted benzonaphthofuranyl group.

[0137] In the compound according to this embodiment, Ar １０１ may be exclusive of benzofluorenes, benzoxanthenes, and dibenzoxanthenes.

[0138] In the compound according to this embodiment, R １０１ ~R １１２ and Ar １０１ It is preferable that at least one of the above has at least one deuterium atom.

[0139] In the compound according to this embodiment, at least R １０１ ~R １１２ It is also preferred that either of the above is a deuterium atom.

[0140] In the compound according to this embodiment, R １０５ , R １０６ , R １０７ , R １０８ , R １１１ , or R １１２ is also preferably a group represented by the general formula (100B). １０６ , R １０７ , R １１１ , or R １１２ is also preferably a group represented by the general formula (100B). １１１ is also preferably a group represented by the general formula (100B). １ is the portion where R １０５ , R １０６ , R１０７ , R １０８ , R １１１ , or R １１２ is a group represented by the general formula (100B), the excitation resistance of the compound according to this embodiment is likely to be improved, and the effect of extending the life of the organic EL device is likely to be obtained.

[0141] In the compound according to this embodiment, R １０１ ~R １１０ and R １１２ It is also preferable that all of are deuterium atoms.

[0142] In the compound according to this embodiment, it is also preferable that all of the groups described as "substituted or unsubstituted" are "unsubstituted" groups, and all of the rings described as "substituted or unsubstituted" are "unsubstituted" rings.

[0143] The compound according to this embodiment is also preferably a compound represented by the following general formula (1A).

[0144]

[0145] (In the general formula (1A), R ４ ~R ８ and R １０ ~R １２ one of R is a group represented by general formula (1B) １ ~R ３ , R ９ and R other than the group represented by general formula (1B). ４ ~R ８ and R １０ ~R １２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R９０５ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ８０１ , and R ８０２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, and in the general formula (1B), n1 is 0 or an integer of 1 or more, and when n1 is an integer of 1 or more, L １represents an unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, provided that the unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring, and １ When there are two or more, there are two or more L １ are the same or different from each other, Ar １ represents an aryl group having four or more substituted or unsubstituted rings fused thereto, or a heterocyclic group having four or more substituted or unsubstituted rings fused thereto, * represents the bonding position with the benz[a]anthracene ring in the general formula (1A), provided that R １ ~R １２ and L in the general formula (1B). １ and Ar １ At least one of the groups has at least one deuterium atom, and L １ When only L has a deuterium atom, １ Among the rings constituting the formula (1A), a deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in the formula (1A).

[0146] In the compound according to this embodiment, n1 is also preferably an integer of 1 or more.

[0147] In the compound according to this embodiment, when n1 is an integer of 1 or more, L １ is also preferably a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms.

[0148] In the compound according to this embodiment, L １ The substituent that is included in is preferably an aryl group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 16 ring atoms, more preferably an aryl group having 6 to 13 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 12 ring atoms, and more preferably a phenyl group or a naphthyl group.

[0149] In the compound according to this embodiment, L １It is also preferred that is unsubstituted.

[0150] In the compound according to this embodiment, L １ is also preferably any of the groups represented by the following general formulae (L1) to (L14): In the examples below, * indicates the bonding position.

[0151]

[0152] In the compound according to this embodiment, n1 is also preferably 0. That is, Ar １ It is also preferred that the benz[a]anthracene ring in the general formula (1A) is directly bonded to the benz[a]anthracene ring in the general formula (1A).

[0153] In the compound according to this embodiment, Ar １ is also preferably a group represented by the following general formula (1B-1), (1B-2), (1B-3), or (1D).

[0154]

[0155] In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), n1 is 0, 1, 2, or 3, and L when n1 is 1, 2, or 3 １ represents an unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, provided that the unsubstituted arylene group having 6 to 50 ring carbon atoms is not a fused ring, and １ When there are two or more, there are two or more L １ are the same or different from each other, and in the general formula (1B-1), R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), and in general formula (1B-2), R ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４are each independently R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ * indicates the bonding position to the benz[a]anthracene ring in the general formula (1A), and in the general formula (1B-3), R ５１ ~R ５５ , and R ８１ ~R ８４ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ５１ ~R ５５ , and R ８１ ~R ８４ are each independently R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ * indicates the bonding position to the benz[a]anthracene ring in the general formula (1A), and in the general formula (1D), R ２１ ~R ３０ indicates a bonding position to the benz[a]anthracene ring in the general formula (1A), and R in the general formula (1D) that is not the bonding position ２１ ~R ３０ at least one pair of adjacent pairs of R in general formula (1D) bond to each other to form a substituted or unsubstituted monocycle, or bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, are not at a bonding position with the benz[a]anthracene ring in general formula (1A), do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ２１ ~R ３０are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and in the groups represented by the general formulae (1B-1), (1B-2), (1B-3), and (1D), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , and R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.)

[0156] In the compound according to this embodiment, Ar １ may be a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted benzonaphthofuranyl group.

[0157] In the compound according to this embodiment, Ar １ may be exclusive of benzofluorenes, benzoxanthenes, and dibenzoxanthenes.

[0158] In the compound according to this embodiment, R １ ~R １２ and Ar １ It is preferable that at least one of the above has at least one deuterium atom.

[0159] In the compound according to this embodiment, at least R １ ~R １２ It is also preferred that either of the above is a deuterium atom.

[0160] In the compound according to this embodiment, R ５ , R ６ , R ７ , R ８ , R １１ , or R １２ is also preferably a group represented by the general formula (1B). ６ , R ７ , R １１ , or R １２ is also preferably a group represented by the general formula (1B). １１ is also preferably a group represented by the general formula (1B). １ is the portion where R ５ , R ６ , R ７ , R８ , R １１ , or R １２ When is a group represented by the general formula (1B), the excitation resistance of the compound according to this embodiment is likely to be improved, and the effect of extending the life of the organic EL device is likely to be obtained.

[0161] In the compound according to this embodiment, R １ ~R １０ and R １２ It is also preferable that all of are deuterium atoms.

[0162] In the compound according to this embodiment, it is also preferable that all of the groups described as "substituted or unsubstituted" are "unsubstituted" groups, and all of the rings described as "substituted or unsubstituted" are "unsubstituted" rings.

[0163] -Method for producing the compound according to this embodiment The compound according to this embodiment can be produced according to the synthesis method described in the Examples below. The compound according to this embodiment can also be produced by following this synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0164] Specific examples of compounds according to this embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula, and a protium atom is represented as H or is not represented at all.

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] Novel proton compounds similar to the compounds represented by the general formula (100A) and the compounds represented by the general formula (1A) include, for example, the following structures.

[0244]

[0245]

[0246] The compound according to this embodiment includes a benz[a]anthracene ring, a linker (L １ Or L １０１ ), and Ar １ Or Ar １０１ Since a deuterium atom is bonded to at least one of the above, the effect of carrier resistance or stabilization of the excited state is high. Therefore, the compound according to this embodiment can be expected to extend the life of an organic EL device. In particular, the singlet energy S １ and triplet energy T １ benz[a]anthracene ring and Ar １ Or Ar １０１ By bonding deuterium atoms to the electrons, it is expected that the electrons will have a longer lifespan.

[0247] Second Embodiment (Organic Electroluminescence Element) An organic EL element according to this embodiment will be described. The organic EL element according to this embodiment contains the compound according to the first embodiment. The organic EL element according to this embodiment has an anode, a cathode, and an organic layer disposed between the anode and the cathode. This organic layer includes at least one layer made of an organic compound. Alternatively, this organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic compound.

[0248] In the organic EL device according to this embodiment, at least one of the organic layers contains the compound according to the first embodiment.

[0249] In the organic EL device of this embodiment, at least one of the organic layers preferably has a light-emitting region. In the organic EL device of this embodiment, the light-emitting region preferably contains at least one light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by general formula (1A). In one embodiment, the light-emitting layer contains a compound represented by general formula (100A).

[0250] The organic EL device according to this embodiment has an anode, a cathode, and an emitting region disposed between the anode and the cathode, and the emitting region includes a first emitting layer and a second emitting layer, and it is also preferable that the first emitting layer contains a first compound represented by general formula (100A) and the second emitting layer contains a second compound.

[0251] The organic EL device according to this embodiment has an anode, a cathode, and an emitting region disposed between the anode and the cathode, and the emitting region includes a first emitting layer and a second emitting layer, and it is also preferable that the first emitting layer contains a first compound represented by general formula (1A) and the second emitting layer contains a second compound.

[0252] When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL element according to this embodiment may have, for example, an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order. Alternatively, the order of the first light-emitting layer and the second light-emitting layer may be reversed, and the organic EL element may have an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.

[0253] When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL device according to this embodiment preferably includes the second light-emitting layer between the anode and the cathode, and the first light-emitting layer is disposed between the anode and the second light-emitting layer. When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL device according to this embodiment preferably includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer is disposed between the anode and the first light-emitting layer.

[0254] (Emission Wavelength of Organic EL Element) The organic EL element according to this embodiment preferably emits light having a maximum peak wavelength of 500 nm or less when the element is driven, and more preferably emits light having a maximum peak wavelength of 430 nm or more and 480 nm or less. The maximum peak wavelength of the light emitted by the organic EL element when the element is driven is measured as follows. ２A voltage is applied to the organic EL element so that the spectral radiance spectrum obtained is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0255] The method for measuring the maximum peak wavelength of a compound in this specification is as follows. －６ mol / L or more 10 －５ A toluene solution of 0.01 mol / L or less is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measurement device is not limited to the device used here. The peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the maximum emission peak wavelength. Note that in this specification, the maximum peak wavelength may also be referred to as the maximum fluorescence emission peak wavelength (FL-peak).

[0256] In the organic EL element according to this embodiment, the organic layer may be composed of only the light-emitting layer, or may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[0257] In the organic EL element according to this embodiment, it is preferable to have a hole transport layer between the anode and the light-emitting region. In the organic EL element according to this embodiment, when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the first light-emitting layer and the second light-emitting layer, it is preferable to have a hole transport layer between the anode and the first light-emitting layer. Furthermore, when the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the second light-emitting layer and the first light-emitting layer, it is preferable to have a hole transport layer between the anode and the second light-emitting layer.

[0258] In the organic EL element according to this embodiment, it is preferable to have an electron transport layer between the cathode and the light-emitting region. In the organic EL element according to this embodiment, when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the first light-emitting layer and the second light-emitting layer, it is preferable to have an electron transport layer between the cathode and the second light-emitting layer. Furthermore, when the stacking order of the first light-emitting layer and the second light-emitting layer is, from the anode side, the second light-emitting layer and the first light-emitting layer, it is preferable to have an electron transport layer between the cathode and the first light-emitting layer.

[0259] Fig. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1A shown in Fig. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A includes, in order from the anode 3 side, a hole transport region 6, an emissive region 5A, and an electron transport region 7. The hole transport region 6 includes, in order from the anode 3 side, a hole injection layer 61 and a hole transport layer 62. The emissive region 5A includes one emissive layer 5. The electron transport region 7 includes, in order from the emissive region 5A side, an electron transport layer 71 and an electron injection layer 72.

[0260] (Light-emitting layer) The light-emitting layer 5 contains the compound according to the first embodiment. In the organic EL device 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the general formula (1A).

[0261] (Light-Emitting Compound) In the organic EL element 1A, the light-emitting layer 5 preferably further contains a light-emitting compound (preferably a fluorescent compound).

[0262] Examples of the light-emitting compound contained in the light-emitting layer 5 include one or more compounds selected from the group consisting of a compound represented by the following general formula (3), a compound represented by the following general formula (4), a compound represented by the following general formula (5), a compound represented by the following general formula (6), a compound represented by the following general formula (7), a compound represented by the following general formula (8), a compound represented by the following general formula (9), and a compound represented by the following general formula (10).

[0263] (Compound Represented by General Formula (3)) The compound represented by general formula (3) will be explained.

[0264]

[0265] (In the general formula (3), R ３０１ ~R ３１０ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３０１ ~R ３１０ at least one of R is a monovalent group represented by the following general formula (31), R does not form the monocycle, does not form the condensed ring, and is not a monovalent group represented by the following general formula (31) ３０１ ~R ３１０ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0266]

[0267] (In the general formula (31), Ar ３０１ and Ar ３０２ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; L ３０１ ~L ３０３are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and * indicates a bonding position on the pyrene ring in general formula (3).

[0268] In the luminescent compound, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ and R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.

[0269] In the general formula (3), R ３０１ ~R ３１０ It is preferable that two of them are groups represented by the general formula (31).

[0270] In one embodiment, the compound represented by the general formula (3) is a compound represented by the following general formula (33).

[0271]

[0272] (In the general formula (33), R ３１１ ~R ３１８ are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). ３０１ ~R ３１０ is synonymous with L ３１１ ~L ３１６ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, ３１２ , Ar ３１３ , Ar ３１５ and Ar ３１６ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0273] In the general formula (31), L ３０１ is preferably a single bond, and L ３０２ and L ３０３ is preferably a single bond.

[0274] In one embodiment, the compound represented by the general formula (3) is represented by the following general formula (34) or (35).

[0275]

[0276] (In the general formula (34), R ３１１ ~R ３１８ are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). ３０１ ~R ３１０ is synonymous with L ３１２ , L ３１３ , L ３１５ and L ３１６each independently represents L in the general formula (33). ３１２ , L ３１３ , L ３１５ and L ３１６ Ar ３１２ , Ar ３１３ , Ar ３１５ and Ar ３１６ are each independently Ar in the general formula (33). ３１２ , Ar ３１３ , Ar ３１５ and Ar ３１６ is synonymous with

[0277]

[0278] (In the general formula (35), R ３１１ ~R ３１８ are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). ３０１ ~R ３１０ Ar ３１２ , Ar ３１３ , Ar ３１５ and Ar ３１６ are each independently Ar in the general formula (33). ３１２ , Ar ３１３ , Ar ３１５ and Ar ３１６ is synonymous with

[0279] In the general formula (31), preferably, Ar ３０１ and Ar ３０２ At least one of the general formulas (33) to (35) is a group represented by the following general formula (36): ３１２ and Ar ３１３ At least one of the general formulas (33) to (35) is a group represented by the following general formula (36): ３１５ and Ar ３１６ At least one of the above is a group represented by the following general formula (36).

[0280]

[0281] (In the general formula (36), X ３represents an oxygen atom or a sulfur atom, R ３２１ ~R ３２７ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocycle or the fused ring ３２１ ~R ３２７ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and * represents L ３０２ , L ３０３ , L ３１２ , L ３１３ , L ３１５ or L ３１６ indicates the bonding position with

[0282] X ３ is preferably an oxygen atom.

[0283] R ３２１ ~R ３２７at least one of the above is preferably 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0284] In the general formula (31), Ar ３０１ is a group represented by the general formula (36), and Ar ３０２ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. ３１２ is a group represented by the general formula (36), and Ar ３１３ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. ３１５ is a group represented by the general formula (36), and Ar ３１６ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0285] In one embodiment, the compound represented by the general formula (3) is represented by the following general formula (37).

[0286]

[0287] (In the general formula (37), R ３１１ ~R ３１８ are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). ３０１ ~R ３１０ is synonymous with R ３２１ ~R ３２７ At least one pair of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３４１ ~R ３４７one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocycle or the fused ring ３２１ ~R ３２７ and R ３４１ ~R ３４７ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ３３１ ~R ３３５ and R ３５１ ~R ３５５ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0288] Specific examples of the compound represented by the general formula (3) include the compounds shown below.

[0289]

[0290]

[0291]

[0292]

[0293]

[0294] (Compound Represented by General Formula (4)) The compound represented by general formula (4) will be explained.

[0295]

[0296] (in the general formula (4), Z's are each independently CRa or a nitrogen atom, ring A1 and ring A2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms, when a plurality of Ra's are present, one or more pairs of adjacent two or more of the plurality of Ra's are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other, n21 and n22 are each independently 0, 1, 2, 3, or 4, when a plurality of Rb's are present, one or more pairs of adjacent two or more of the plurality of Rb's are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other, When a plurality of Rc's are present, one or more pairs of adjacent two or more of the plurality of Rc's bond to each other to form a substituted or unsubstituted monocycle, or bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, and Ra, Rb and Rc that do not form the monocycle and the fused ring each independently represent 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0297] The "aromatic hydrocarbon rings" of rings A1 and A2 have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group". The "aromatic hydrocarbon rings" of rings A1 and A2 contain, as ring-forming atoms, the two carbon atoms on the central fused bicyclic structure of general formula (4). 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.

[0298] The "heterocycles" of rings A1 and A2 have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group". The "heterocycles" of rings A1 and A2 contain the two carbon atoms on the central fused bicyclic structure of general formula (4) 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.

[0299] 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.

[0300] 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.

[0301] At least one of Ra, Rb, and Rc is preferably a group represented by the following general formula (4a), and more preferably at least two of them are groups represented by the following general formula (4a).

[0302]

[0303] (In the general formula (4a), L ４０１ represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, ４０１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following general formula (4b):

[0304]

[0305] (In the general formula (4b), L ４０２ and L ４０３ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, ４０２ and Ar ４０３ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and are not bonded to each other to form the monocyclic ring or the fused ring. ４０２ and Ar ４０３ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0306] In one embodiment, the compound represented by the general formula (4) is represented by the following general formula (42).

[0307]

[0308] (In the general formula (42), R ４０１ ~R ４１１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocyclic ring or the fused ring. ４０１ ~R ４１１ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0309] R ４０１ ~R ４１１ Among R, at least one is preferably a group represented by the general formula (4a), and more preferably at least two are groups represented by the general formula (4a). ４０４ and R ４１１ is preferably a group represented by the general formula (4a).

[0310] In one embodiment, the compound represented by the general formula (4) is a compound having a structure represented by the following general formula (4-1) or (4-2) bonded to the A1 ring. In another embodiment, the compound represented by the general formula (42) is a compound having a structure represented by the following general formula (4-3) or (4-4) bonded to the A1 ring. ４０４ ~R ４０７ is a compound in which a structure represented by the following general formula (4-1) or (4-2) is bonded to a ring to which

[0311]

[0312] (In the general formula (4-1), two * are each independently bonded to a ring-forming carbon atom of an aromatic hydrocarbon ring or a ring-forming atom of a heterocycle as the A1 ring in the general formula (4), or to a ring-forming atom of R in the general formula (42). ４０４ ~R ４０７ The three * in the general formula (4-2) are each independently bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle as the A1 ring in the general formula (4), or bonded to R in the general formula (42). ４０４ ~R ４０７ and R ４２１ ~R ４２７one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ４３１ ~R ４３８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocyclic ring or the fused ring. ４２１ ~R ４２７ and R ４３１ ~R ４３８ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0313] In one embodiment, the compound represented by the general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4), or general formula (41-5).

[0314]

[0315]

[0316]

[0317] (In the general formula (41-3), general formula (41-4) and general formula (41-5), the A1 ring is as defined in the general formula (4), and R ４２１ ~R ４２７ are each independently R in the general formula (4-1). ４２１ ~R ４２７ is synonymous with R ４４０ ~R ４４８ are each independently R in the general formula (42). ４０１ ~R ４１１ is synonymous with

[0318] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms as ring A1 in general formula (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring.

[0319] In one embodiment, the substituted or unsubstituted heterocycle having 5 to 50 ring atoms as ring A1 in general formula (41-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[0320] In one embodiment, the compound represented by the general formula (4) or the general formula (42) is selected from the group consisting of compounds represented by the following general formulas (461) to (467).

[0321]

[0322]

[0323]

[0324]

[0325]

[0326] (In the general formula (461), the general formula (462), the general formula (463), the general formula (464), the general formula (465), the general formula (466) and the general formula (467), R ４２１ ~R ４２７ are each independently R in the general formula (4-1).４２１ ~R ４２７ is synonymous with R ４３１ ~R ４３８ are each independently R in the general formula (4-2). ４３１ ~R ４３８ is synonymous with R ４４０ ~R ４４８ and R ４５１ ~R ４５４ are each independently R in the general formula (42). ４０１ ~R ４１１ is synonymous with X ４ is an oxygen atom, NR ８０１ , or C(R ８０２ ) (R ８０３ ) and R ８０１ , R ８０２ and R ８０３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ８０３ If there are multiple R ８０３ are the same or different from each other.)

[0327] In one embodiment, the compound represented by the general formula (42) is R ４０１ ~R ４１１ one or more pairs of adjacent two or more of these are bonded to each other to form a substituted or unsubstituted monocycle, or are bonded to each other to form a substituted or unsubstituted fused ring, and this embodiment will be described in detail below as a compound represented by general formula (45).

[0328] (Compound Represented by General Formula (45)) The compound represented by general formula (45) will be described.

[0329]

[0330] (In the general formula (45), R ４６１ and R ４６２ A set consisting of ４６２ and R ４６３ A set consisting of ４６４ and R ４６５ A set consisting of ４６５ and R ４６６ A set consisting of ４６６ and R ４６７ A set consisting of ４６８ and R ４６９ A set consisting of ４６９ and R ４７０ and R ４７０ and R ４７１ and two or more of the pairs selected from the group consisting of pairs of R and R are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, ４６１ and R ４６２ and R ４６２ and R ４６３ A set consisting of: R ４６４ and R ４６５ and R ４６５ and R ４６６ A set consisting of: R ４６５ and R ４６６ and R ４６６ and R ４６７ A set consisting of: R ４６８ and R ４６９ and R ４６９ and R ４７０ and R ４６９ and R ４７０ and R ４７０ and R ４７１ and R do not simultaneously form a ring. ４６１ ~R ４７１ The two or more rings formed by R are the same as or different from each other, and R does not form the single ring and does not form the fused ring. ４６１ ~R ４７１are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0331] In the general formula (45), R ｎ and R ｎ＋１ (n represents an integer selected from 461, 462, 464 to 466, and 468 to 470) are bonded to each other to form R ｎ and R ｎ＋１ is bonded to the two ring-forming carbon atoms to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from the group consisting of carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, and more preferably 5 or 6.

[0332] The number of the ring structures in the compound represented by the general formula (45) is, for example, two, three, or four. The two or more ring structures may be present on the same benzene ring on the parent skeleton of the general formula (45), or may be present on different benzene rings. For example, when the compound has three ring structures, one ring structure may be present on each of the three benzene rings in the general formula (45).

[0333] Examples of the ring structure in the compound represented by the general formula (45) include structures represented by the following general formulae (451) to (460).

[0334]

[0335] (In the general formulae (451) to (457), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 each represent R ｎ and R ｎ＋１ represents the two ring-forming carbon atoms to which R is bonded; ｎ The ring-forming carbon atom to which is bonded may be either of the two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14, ４５ is C(R ４５１２ ) (R ４５１３ ), N.R. ４５１４ , an oxygen atom or a sulfur atom, R ４５０１ ~R ４５０６ and R ４５１２ ~R ４５１３ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocyclic ring or the fused ring. ４５０１ ~R ４５１４ are each independently R in the general formula (45). ４６１ ~R ４７１ is synonymous with

[0336]

[0337] (In the general formulae (458) to (460), *1 and *2, and *3 and *4 are each R ｎ and R ｎ＋１ represents the two ring-forming carbon atoms to which R is bonded; ｎ The ring carbon atoms to which X is bonded may be either the two ring carbon atoms represented by *1 and *2, or the two ring carbon atoms represented by *3 and *4, ４５ is C(R ４５１２ ) (R ４５１３ ), N.R. ４５１４ , an oxygen atom or a sulfur atom, R ４５１２ ~R ４５１３ and R ４５１５ ~R ４５２５one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocyclic ring or the fused ring. ４５１２ ~R ４５１３ , R ４５１５ ~R ４５２１ and R ４５２２ ~R ４５２５ , and R ４５１４ are each independently R in the general formula (45). ４６１ ~R ４７１ is synonymous with

[0338] In the general formula (45), R ４６２ , R ４６４ , R ４６５ , R ４７０ and R ４７１ At least one of (preferably, R ４６２ , R ４６５ and R ４７０ At least one of, more preferably R ４６２ ) is preferably a group that does not form a ring structure.

[0339] (i) In the general formula (45), R ｎ and R ｎ＋１ (ii) a substituent when the ring structure formed by the formula (45) has a substituent, ４６１ ~R ４７１ (iii) R in formulas (451) to (460) ４５０１ ~R ４５１４ , R ４５１５ ~R ４５２５ are preferably each independently a hydrogen atom, 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) a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group selected from the group consisting of groups represented by the following general formulae (461) to (464):

[0340]

[0341] (In the general formulae (461) to (464), R ｄ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ４６ is C(R ８０１ ) (R ８０２ ), N.R. ８０３ , an oxygen atom or a sulfur atom, R ８０１ , R ８０２ and R ８０３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R ８０１ If there are multiple R ８０１are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ８０３ If there are multiple R ８０３ are the same or different from each other, p1 is 5, p2 is 4, p3 is 3, and p4 is 7, and * in the general formulae (461) to (464) each independently indicates a bonding position with a ring structure. ９０１ ~R ９０７ is as defined above.

[0342] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-1) to (45-6).

[0343]

[0344]

[0345] (In the general formulae (45-1) to (45-6), rings d to i are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, R ４６１ ~R ４７１ are each independently R in the general formula (45). ４６１ ~R ４７１ is synonymous with

[0346] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-7) to (45-12).

[0347]

[0348]

[0349] (In the general formulae (45-7) to (45-12), rings d to f, k, and j each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, and R ４６１ ~R ４７１ are each independently R in the general formula (45). ４６１ ~R ４７１is synonymous with

[0350] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-13) to (45-21).

[0351]

[0352]

[0353]

[0354] (In the general formulae (45-13) to (45-21), rings d to k each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, and R ４６１ ~R ４７１ are each independently R in the general formula (45). ４６１ ~R ４７１ is synonymous with

[0355] In the case where the ring g or the ring h further has a substituent, examples of the substituent include a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a group represented by the general formula (461), a group represented by the general formula (463), or a group represented by the general formula (464).

[0356] In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-22) to (45-25).

[0357]

[0358] (In the general formulae (45-22) to (45-25), X ４６ and X ４７ are each independently C(R ８０１ ) (R ８０２ ), N.R. ８０３ , an oxygen atom or a sulfur atom, R ４６１ ~R ４７１ and R ４８１ ~R ４８８ are each independently R in the general formula (45). ４６１ ~R ４７１It is synonymous with R ８０１ , R ８０２ and R ８０３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ８０３ If there are multiple R ８０３ are the same or different from each other.)

[0359] In one embodiment, the compound represented by the general formula (45) is represented by the following general formula (45-26).

[0360]

[0361] (In the general formula (45-26), X ４６ is C(R ８０１ ) (R ８０２ ), N.R. ８０３ , an oxygen atom or a sulfur atom, R ４６３ , R ４６４ , R ４６７ , R ４６８ , R ４７１ , and R ４８１ ~R ４９２ are each independently R in the general formula (45). ４６１ ~R ４７１ It is synonymous with R ８０１ , R ８０２ and R ８０３are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ８０３ If there are multiple R ８０３ are the same or different from each other.)

[0362] Specific examples of the compound represented by the general formula (4) include the compounds shown below: In the specific examples below, Ph represents a phenyl group, and D represents a deuterium atom.

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373] (Compound Represented by General Formula (5)) The compound represented by general formula (5) will be described. The compound represented by general formula (5) corresponds to the compound represented by general formula (41-3) described above.

[0374]

[0375] (In the general formula (5), R ５０１ ~R ５０７ and R ５１１ ~R ５１７ one or more pairs of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocycle or the fused ring ５０１ ~R ５０７ and R ５１１ ~R ５１７ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ５２１ and R ５２２ are each independently a hydrogen atom, 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 ) (R９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0376] "R ５０１ ~R ５０７ and R ５１１ ~R ５１７ "One set of two or more adjacent pairs of R ５０１ and R ５０２ A set consisting of R ５０２ and R ５０３ A set consisting of R ５０３ and R ５０４ A set consisting of R ５０５ and R ５０６ A set consisting of R ５０６ and R ５０７ A set consisting of R ５０１ and R ５０２ and R ５０３ It is a combination of a set consisting of:

[0377] In one embodiment, R ５０１ ~R ５０７ and R ５１１ ~R ５１７ At least one, preferably two of the following are -N(R ９０６ ) (R ９０７ ) is a group represented by the formula:

[0378] In one embodiment, R ５０１ ~R ５０７ and R ５１１ ~R ５１７ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0379] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52):

[0380]

[0381] (In the general formula (52), R ５３１ ~R ５３４ and R ５４１ ~R ５４４ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the monocyclic ring or the fused ring. ５３１ ~R ５３４ , R ５４１ ~R ５４４ , and R ５５１ and R ５５２ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ５６１ ~R ５６４ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0382] In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (53):

[0383]

[0384] (In the general formula (53), R ５５１ , R ５５２ and R ５６１ ~R ５６４ are each independently R in the general formula (52). ５５１ , R ５５２ and R ５６１ ~R ５６４ is synonymous with

[0385] In one embodiment, R in the general formula (52) and the general formula (53) ５６１ ~R ５６４ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

[0386] In one embodiment, R in the general formula (5) ５２１ and R ５２２ , R in the general formula (52) and the general formula (53) ５５１ and R ５５２ is a hydrogen atom.

[0387] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the general formula (5), the general formula (52), and the general formula (53) 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, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0388] Specific examples of the compound represented by the general formula (5) include the compounds shown below.

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406] (Compound Represented by General Formula (6)) The compound represented by general formula (6) will be explained.

[0407]

[0408] (In the general formula (6), the ring a, the ring b, and the ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, and R ６０１ and R ６０２ each independently bond to the ring a, ring b or ring c to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle, ６０１ and R ６０２ 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0409] 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 general formula (6) composed of a boron atom and two nitrogen atoms.

[0410] 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 includes three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms.

[0411] 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 "heterocyclic rings" 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 "heterocyclic ring" of ring a includes three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "heterocyclic rings" of ring b and ring c include two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. Specific examples of "substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.

[0412] R ６０１ and R ６０２ 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 the general formula (6). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. ６０１ and R ６０２ 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 ６０１ and R ６０２ It means that the atoms constituting R are bonded together. ６０１ is bonded to ring a, and R ６０１ A two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring may be formed by condensing a ring containing R with ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring condensed heterocyclic groups in specific example group G2. ６０１ When is bonded to ring b, R ６０２ When R is bonded to ring a,６０２ The same applies when is bonded to ring c.

[0413] In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having ring carbon atoms of 6 to 50. In one embodiment, the ring a, ring b, and ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0414] In one embodiment, R in the general formula (6) ６０１ and R ６０２ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0415] In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62).

[0416]

[0417] (In the general formula (62), R ６０１Ａ is R ６１１ and R ６２１ R ６０２Ａ is R ６１３ and R ６１４ or a substituted or unsubstituted heterocyclic ring, or a substituted or unsubstituted heterocyclic ring is not formed by bonding to one or more selected from the group consisting of ６０１Ａ and R ６０２Ａare 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ６１１ ~R ６２１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted heterocycle, do not form the monocycle, and do not form the fused ring ６１１ ~R ６２１ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0418] R in the general formula (62) ６０１Ａ and R ６０２Ａ are R in the general formula (6), respectively. ６０１ and R ６０２ For example, R ６０１Ａ and R ６１１may be bonded to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle in which a ring containing the ring is fused with a benzene ring corresponding to ring a. 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. ６０１Ａ and R ６２１ When R ６０２Ａ and R ６１３ is bonded, and R ６０２Ａ and R ６１４ The same applies when the two are combined.

[0419] R ６１１ ~R ６２１ One or more pairs of adjacent two or more of R 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. For example, R ６１１ and R ６１２ 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.

[0420] In one embodiment, R ６１１ ~R ６２１ 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 heterocyclic group having 5 to 50 ring atoms.

[0421] In one embodiment, R ６１１ ~R ６２１ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0422] In one embodiment, R ６１１ ~R ６２１are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0423] In one embodiment, R ６１１ ~R ６２１ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; R ６１１ ~R ６２１ At least one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0424] In one embodiment, the compound represented by the general formula (62) is a compound represented by the following general formula (63):

[0425]

[0426] (In the general formula (63), R ６３１ is R ６４６ R may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle; ６３３ is R ６４７ R may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle; ６３４ is R ６５１ R may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle; ６４１ is R ６４２ R may be bonded to form a substituted or unsubstituted heterocycle, or may not form a substituted or unsubstituted heterocycle; ６３１ ~R ６５１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, do not form the substituted or unsubstituted heterocycle, do not form the monocycle, and do not form the fused ring ６３１ ~R ６５１are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0427] R ６３１ is R ６４６ may be bonded to form a substituted or unsubstituted heterocycle. For example, R ６３１ and R ６４６ is bonded to form R ６４６ may be bonded to a benzene ring, a ring containing N, and a benzene ring corresponding to ring a, which are fused to form a nitrogen-containing heterocyclic ring having three or more fused rings. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more fused rings in the specific example group G2. ６３３ and R ６４７ When R ６３４ and R ６５１ is bonded, and R ６４１ and R ６４２ The same applies when the two are combined.

[0428] In one embodiment, R ６３１ ~R ６５１ 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 heterocyclic group having 5 to 50 ring atoms.

[0429] In one embodiment, R６３１ ~R ６５１ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0430] In one embodiment, R ６３１ ~R ６５１ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0431] In one embodiment, R ６３１ ~R ６５１ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; R ６３１ ~R ６５１ At least one of the groups is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0432] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63A):

[0433]

[0434] (In the general formula (63A), R ６６１ is a hydrogen atom, 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R ６６２ ~R ６６５ 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0435] In one embodiment, R６６１ ~R ６６５ 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.

[0436] In one embodiment, R ６６１ ~R ６６５ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0437] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B):

[0438]

[0439] (In the general formula (63B), R ６７１ and R ６７２ are each independently a hydrogen atom, 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, ６７３ ~R ６７５ each independently represents 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0440] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63B').

[0441]

[0442] (In the general formula (63B′), R ６７２ ~R ６７５ are each independently R in the general formula (63B). ６７２ ~R ６７５ is synonymous with

[0443] In one embodiment, R ６７１ ~R ６７５ At least one of the above 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, -N(R ９０６ ) (R ９０７ ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0444] In one embodiment, R ６７２ represents a hydrogen atom, 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, ６７１ and R ６７３ ~R ６７５ are each independently 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.

[0445] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C):

[0446]

[0447] (In the general formula (63C), R ６８１ and R ６８２are each independently a hydrogen atom, 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. ６８３ ~R ６８６ 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0448] In one embodiment, the compound represented by the general formula (63) is a compound represented by the following general formula (63C').

[0449]

[0450] (In the general formula (63C'), R ６８３ ~R ６８６ are each independently R in the general formula (63C). ６８３ ~R ６８６ is synonymous with

[0451] In one embodiment, R ６８１ ~R ６８６ 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.

[0452] In one embodiment, R ６８１ ~R ６８６ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0453] The compound represented by the general formula (6) is first prepared by connecting the ring a, ring b and ring c to a linking group (N—R ６０１ and groups containing N-R ６０２An intermediate is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (reaction 1), and the final product is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (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 or the like can be applied.

[0454] Specific examples of the compound represented by the general formula (6) are listed below, but these are merely illustrative, and the compound represented by the general formula (6) is not limited to the following specific examples.

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473] (Compound Represented by General Formula (7)) The compound represented by general formula (7) will be explained.

[0474]

[0475]

[0476] (In the general formula (7), the r ring is a ring represented by the general formula (72) or the general formula (73) and fused at any position to the adjacent ring, the q ring and the s ring are each independently a ring represented by the general formula (74) and fused at any position to the adjacent ring, the p ring and the t ring are each independently a structure represented by the general formula (75) or the general formula (76) and fused at any position to the adjacent ring, and X ７ represents an oxygen atom, a sulfur atom, or NR ７０２ It is. ７０１ When there are multiple R ７０１ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R is not bonded to each other to form a monocyclic ring or a fused ring. ７０１ and R ７０２ each independently represents 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ７０１ and Ar ７０２are 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; ７０１ represents a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, m1 is 0, 1 or 2, m2 is 0, 1, 2, 3 or 4, m3 is independently 0, 1, 2 or 3, and m4 is independently 0, 1, 2, 3, 4 or 5, R ７０１ If there are multiple R ７０１ are the same or different from each other, and X ７ If there are multiple Xs, ７ are the same or different from each other, R ７０２ If there are multiple R ７０２ are the same or different from each other, Ar ７０１ When there are multiple Ar ７０１ are the same or different from each other, Ar ７０２ When there are multiple Ar ７０２ are the same or different from each other, and L ７０１ If there are multiple L ７０１ are the same or different from each other.)

[0477] In the general formula (7), each of the p, q, r, s, and t rings is fused to an adjacent ring by sharing two carbon atoms. The fused position and orientation are not limited, and fusion is possible at any position and orientation.

[0478] In one embodiment, in the general formula (72) or (73) as the r ring, m1=0 or m2=0.

[0479] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulae (71-1) to (71-6).

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486] (In the general formulas (71-1) to (71-6), R ７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m1 and m3 are each R in the general formula (7). ７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m1 and m3 are synonymous with each other.)

[0487] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-11) to (71-13).

[0488]

[0489]

[0490]

[0491] (In the general formulas (71-11) to (71-13), R ７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m1, m3 and m4 are each R in the general formula (7).７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m1, m3 and m4.)

[0492] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulae (71-21) to (71-25).

[0493]

[0494]

[0495]

[0496]

[0497]

[0498] (In the general formulas (71-21) to (71-25), R ７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m1 and m4 are each R in the general formula (7). ７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m1 and m4 are synonymous.)

[0499] In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulae (71-31) to (71-33).

[0500]

[0501]

[0502]

[0503] (In the general formulas (71-31) to (71-33), R ７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m2 to m4 are each R in the general formula (7).７０１ , X ７ , Ar ７０１ , Ar ７０２ , L ７０１ , m2 to m4.)

[0504] In one embodiment, Ar ７０１ and Ar ７０２ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0505] In one embodiment, Ar ７０１ and Ar ７０２ one of Ar and Ar is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; ７０１ and Ar ７０２ The other is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0506] Specific examples of the compound represented by the general formula (7) include the compounds shown below.

[0507]

[0508]

[0509]

[0510]

[0511]

[0512]

[0513] (Compound Represented by General Formula (8)) The compound represented by general formula (8) will be explained.

[0514]

[0515] (In the general formula (8), R ８０１ and R ８０２ , R ８０２ and R ８０３ , and R ８０３ and R ８０４ At least one pair of R is bonded to each other to form a divalent group represented by the following general formula (82), ８０５ and R ８０６ , R８０６ and R ８０７ , and R ８０７ and R ８０８ At least one pair of these bonds together to form a divalent group represented by the following general formula (83):

[0516]

[0517] (R which does not form a divalent group represented by the general formula (82) ８０１ ~R ８０４ , and R ８１１ ~R ８１４ At least one of R is a monovalent group represented by the following general formula (84), and R does not form a divalent group represented by the general formula (83). ８０５ ~R ８０８ , and R ８２１ ~R ８２４ At least one of X is a monovalent group represented by the following general formula (84): ８ is an oxygen atom, a sulfur atom, or NR ８０９ R does not form a divalent group represented by the general formula (82) or the general formula (83), and is not a monovalent group represented by the general formula (84). ８０１ ~R ８０８ , R which is not a monovalent group represented by the general formula (84) ８１１ ~R ８１４ and R ８２１ ~R ８２４ , and R ８０９ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0518]

[0519] (In the general formula (84), Ar ８０１ and Ar ８０２ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; L ８０１ ~L ８０３ are each independently a 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 a divalent linking group formed by bonding two to four groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and * in the general formula (84) indicates the bonding position with the ring structure represented by the general formula (8) or the group represented by the general formula (82) or (83).

[0520] In the general formula (8), the positions at which the divalent group represented by the general formula (82) and the divalent group represented by the general formula (83) are formed are not particularly limited, and R ８０１ ~R ８０８ The group can be formed at any possible position.

[0521] In one embodiment, the compound represented by the general formula (8) is represented by any one of the following general formulae (81-1) to (81-6).

[0522]

[0523]

[0524]

[0525] (In the general formulae (81-1) to (81-6), X ８ represents X in the general formula (8).８ is synonymous with R ８０１ ~R ８２４ At least two of R are monovalent groups represented by the general formula (84), and R is not a monovalent group represented by the general formula (84). ８０１ ~R ８２４ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0526] In one embodiment, the compound represented by the general formula (8) is represented by any one of the following general formulae (81-7) to (81-18).

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533] (In the general formulae (81-7) to (81-18), X ８ represents X in the general formula (8). ８ * is a single bond bonding to the monovalent group represented by general formula (84), R８０１ ~R ８２４ are each independently a monovalent group other than the monovalent group represented by the general formula (84) in the general formulas (81-1) to (81-6). ８０１ ~R ８２４ is synonymous with

[0534] R which does not form a divalent group represented by the general formula (82) and the general formula (83) and is not a monovalent group represented by the general formula (84) ８０１ ~R ８０８ and R which is not a monovalent group represented by the general formula (84). ８１１ ~R ８１４ and R ８２１ ~R ８２４ are preferably each independently a hydrogen atom, 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 a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0535] The monovalent group represented by the general formula (84) is preferably represented by the following general formula (85) or general formula (86).

[0536]

[0537] (In the general formula (85), R ８３１ ~R ８４０ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and * in the general formula (85) has the same meaning as * in the general formula (84).

[0538]

[0539] (In the general formula (86), Ar ８０１ , L ８０１ and L ８０３ is Ar in the general formula (84). ８０１ , L ８０１ and L ８０３ is synonymous with HAr ８０１ is a structure represented by the following general formula (87):

[0540]

[0541] (In the general formula (87), X ８１ is an oxygen atom or a sulfur atom, R ８４１ ~R ８４８ Any one of the following is L ８０３ R is a single bond that bonds to ８４１ ~R ８４８ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0542] Specific examples of the compound represented by the general formula (8) include the compounds described in WO 2014 / 104144 and the compounds shown below.

[0543]

[0544]

[0545]

[0546]

[0547]

[0548]

[0549] (Compound Represented by General Formula (9)) The compound represented by general formula (9) will be explained.

[0550]

[0551] (In the general formula (9), A ９１ Ring and A ９２ The rings are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, ９１ Ring and A ９２ One or more rings selected from the group consisting of rings are bonded to * in the structure represented by the following general formula (92):

[0552]

[0553] (In the general formula (92), A ９３ The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, ９ is NR ９３ , C(R ９４ ) (R ９５ ), Si(R ９６ ) (R ９７ ), Ge(R ９８ ) (R ９９ ), an oxygen atom, a sulfur atom, or a selenium atom; R９１ and R ９２ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R is not bonded to each other to form a monocyclic ring or a fused ring. ９１ and R ９２ , and R ９３ ~R ９９ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0554] A ９１ Ring and A ９２ One or more rings selected from the group consisting of rings are bonded to * in the structure represented by the general formula (92). ９１ A ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle is bonded to * in the structure represented by general formula (92). ９２ A ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle is bonded to * in the structure represented by general formula (92).

[0555] In one embodiment, A ９１ Ring and A ９２ A group represented by the following general formula (93) is bonded to one or both of the rings.

[0556]

[0557] (In the general formula (93), Ar ９１ and Ar ９２ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; L ９１ ~L ９３ are each independently a 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 a divalent linking group formed by the bonding of 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, and * in the general formula (93) represents A ９１ Ring and A ９２ Indicates the bonding position to one of the rings.)

[0558] In one embodiment, A ９１ In addition to the ring, A ９２ A ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle is bonded to * in the structure represented by general formula (92). In this case, the structures represented by general formula (92) may be the same or different from each other.

[0559] In one embodiment, R ９１ and R ９２ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. ９１ and R ９２ are bonded to each other to form a fluorene structure.

[0560] In one embodiment, ring A ９１ and Ring A ９２ are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[0561] In one embodiment, ring A ９３is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring. ９ is an oxygen atom or a sulfur atom.

[0562] Specific examples of the compound represented by the general formula (9) include the compounds shown below.

[0563]

[0564]

[0565]

[0566]

[0567] (Compound Represented by General Formula (10)) The compound represented by general formula (10) will be explained.

[0568]

[0569]

[0570] (In the general formula (10), Ax １ The ring is a ring represented by the general formula (10a) and fused to an adjacent ring at any position, and Ax ２ The ring is a ring represented by the general formula (10b) which is fused at any position to an adjacent ring, and two * in the general formula (10b) represent Ax ３ It bonds to any position of the ring, and X Ａ and X Ｂ are each independently C(R １００３ ) (R １００４ ), Si(R １００５ ) (R １００６ ), an oxygen atom or a sulfur atom, ３ The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, １００１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R １００１ ~R１００６ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, mx1 is 3, mx2 is 2, and a plurality of R １００１ are the same or different from each other, and a plurality of R １００２ are the same or different from each other, ax is 0, 1 or 2, when ax is 0 or 1, the structures in the brackets shown as "3-ax" are the same or different from each other, when ax is 2, a plurality of Ar １００１ are the same or different from each other.)

[0571] In one embodiment, Ar １００１ represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0572] In one embodiment, Ax ３ The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[0573] In one embodiment, R １００３ and R １００４ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0574] In one embodiment, ax is 1.

[0575] Specific examples of the compound represented by the general formula (10) include the compounds shown below.

[0576]

[0577] In one embodiment, the light-emitting layer 5 contains, as a light-emitting compound, one or more compounds selected from the group consisting of a compound represented by the general formula (4), a compound represented by the general formula (5), a compound represented by the general formula (6), and a compound represented by the following general formula (63a):

[0578]

[0579] (In the general formula (63a), R ６３１ is R ６４６ R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. ６３３ is R ６４７ R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. ６３４ is R ６５１ R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. ６４１ is R ６４２ R may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. ６３１ ~R ６５１ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted heterocycle, the monocycle, or the fused ring. ６３１ ~R ６５１are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, provided that R does not form the substituted or unsubstituted heterocyclic ring, does not form the monocyclic ring, and does not form the fused ring. ６３１ ~R ６５１ at least one of the following is a halogen atom, a cyano group, a nitro group, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0580] In one embodiment, the compound represented by the general formula (4) is a compound represented by the general formula (41-3), the general formula (41-4), or the general formula (41-5), and the A1 ring in the general formula (41-5) is a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, or a substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms.

[0581] In one embodiment, in the general formulas (41-3), (41-4), and (41-5), the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring, and the substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[0582] In one embodiment, in the general formula (41-3), the general formula (41-4), or the general formula (41-5), the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring, and the substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[0583] In one embodiment, the compound represented by general formula (4) is selected from the group consisting of a compound represented by the following general formula (461), a compound represented by the following general formula (462), a compound represented by the following general formula (463), a compound represented by the following general formula (464), a compound represented by the following general formula (465), a compound represented by the following general formula (466), and a compound represented by the following general formula (467).

[0584]

[0585]

[0586]

[0587]

[0588]

[0589] (In the general formulae (461) to (467), R ４２１ ~R ４２７ , R ４３１ ~R ４３６ , R ４４０ ~R ４４８ and R ４５１ ~R ４５４ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ４３７ , R ４３８ and R which does not form the monocyclic ring and does not form the fused ring. ４２１ ~R ４２７ , R ４３１ ~R ４３６ , R ４４０ ~R ４４８ and R ４５１ ~R ４５４ are each independently a hydrogen atom, 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 a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ) a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ４ is an oxygen atom, NR ８０１, or C(R ８０２ ) (R ８０３ ) and R ８０１ , R ８０２ and R ８０３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, R ８０３ If there are multiple R ８０３ are the same or different from each other.)

[0590] In one embodiment, R ４２１ ~R ４２７ and R ４４０ ~R ４４８ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0591] In one embodiment, R ４２１ ~R ４２７ and R ４４０ ~R ４４７ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0592] In one embodiment, the compound represented by the general formula (41-3) is a compound represented by the following general formula (41-3-1):

[0593]

[0594] (In the general formula (41-3-1), R ４２３ , R ４２５ , R ４２６ , R ４４２ , R ４４４ and R ４４５ are each independently R in the general formula (41-3). ４２３ , R ４２５ , R ４２６ , R ４４２ , R ４４４ and R ４４５ is synonymous with

[0595] In one embodiment, the compound represented by the general formula (41-3) is a compound represented by the following general formula (41-3-2):

[0596]

[0597] (In the general formula (41-3-2), R ４２１ ~R ４２７ and R ４４０ ~R ４４８ are each independently R in the general formula (41-3). ４２１ ~R ４２７ and R ４４０ ~R ４４８ However, R ４２１ ~R ４２７ and R ４４０ ~R ４４６ At least one of the groups is —N(R ９０６ ) (R ９０７ ) is a group represented by

[0598] In one embodiment, in the general formula (41-3-2), R ４２１ ~R ４２７ and R ４４０ ~R ４４６ Any two of -N(R ９０６ ) (R ９０７ ) is a group represented by the formula:

[0599] In one embodiment, the compound represented by the general formula (41-3-2) is a compound represented by the following formula (41-3-3):

[0600]

[0601] (In the general formula (41-3-3), R ４２１ ~R ４２４ , R ４４０ ~R ４４３ , R ４４７ and R ４４８ are each independently R in the general formula (41-3). ４２１ ~R ４２４ , R ４４０ ~R ４４３ , R ４４７ and R ４４８ is synonymous with R Ａ , R Ｂ , R Ｃ and R Ｄ are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0602] In one embodiment, the compound represented by the general formula (41-3-3) is a compound represented by the following formula (41-3-4):

[0603]

[0604] (In the general formula (41-3-4), R ４４７ , R ４４８ , R Ａ , R Ｂ , R Ｃ and R Ｄ each independently represents R in the general formula (41-3-3). ４４７ , R ４４８ , R Ａ , R Ｂ , R Ｃ and R Ｄ is synonymous with

[0605] In one embodiment, R Ａ , R Ｂ , R Ｃ and R Ｄ are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0606] In one embodiment, R Ａ , R Ｂ , R Ｃ and R Ｄare each independently a substituted or unsubstituted phenyl group.

[0607] In one embodiment, R ４４７ and R ４４８ is a hydrogen atom.

[0608] In organic EL device 1A, the light-emitting compound contained in light-emitting layer 5 is preferably a compound that exhibits emission with a maximum peak wavelength of 500 nm or less, more preferably a compound that exhibits emission with a maximum peak wavelength of 430 nm or more and 480 nm or less. In organic EL device 1A, the light-emitting compound contained in light-emitting layer 5 is preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 500 nm or less, more preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.

[0609] In the organic EL element 1A, when the light-emitting layer 5 contains the compound according to the first embodiment and a light-emitting compound, the compound according to the first embodiment is preferably a host material (sometimes referred to as a matrix material), and the light-emitting compound is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a light-emitting material).

[0610] In this specification, the term "host material" refers to a material that is contained in, for example, "50% by mass or more of the layer." Thus, for example, in the case of organic EL element 1A, light-emitting layer 5 contains the compound represented by general formula (1A) in an amount of 50% by mass or more of the total mass of the light-emitting layer.

[0611] (Thickness of the Light-Emitting Layer) The thickness of the light-emitting layer 5 is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity. When the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in driving voltage.

[0612] (Compound Content in Light-Emitting Layer) When the light-emitting layer 5 contains the compound according to the first embodiment and the light-emitting compound, the contents of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 are preferably, for example, in the following ranges, respectively. The content of the compound according to the first embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 is 100% by mass.

[0613] Note that this embodiment does not exclude the case where the light-emitting layer 5 contains materials other than the compound according to the first embodiment and the light-emitting compound. The light-emitting layer 5 may contain only one type of compound according to the first embodiment, or may contain two or more types of light-emitting compounds. The light-emitting layer 5 may contain only one type of light-emitting compound, or may contain two or more types of light-emitting compounds.

[0614] Fig. 2 shows a schematic configuration of another example of an organic EL element according to this embodiment. The organic EL element 1B shown in Fig. 2 differs from the organic EL element 1A in that the organic layer 10B includes a first light-emitting region 5B, but is otherwise similar to the organic EL element 1A. The first light-emitting region 5B includes, in this order from the anode 3 side, a first light-emitting layer 51 and a second light-emitting layer 52. The first light-emitting layer 51 contains a first compound, and the second light-emitting layer 52 contains a second compound.

[0615] (First Compound) In organic EL element 1B, the first compound is the compound according to the first embodiment. In the organic EL element according to this embodiment, the first compound is preferably a compound represented by general formula (100A). The first compound may be a compound represented by general formula (1A).

[0616] (Second Compound) In the organic EL element 1B, the second compound is a compound represented by the following general formula (2).

[0617]

[0618] (In the general formula (2), R ２０１ ~R ２０８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and L ２０１ and L ２０２ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ２０１ and Ar ２０２ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0619] (In the second compound according to this embodiment, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ８０１ and R８０２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other.)

[0620] In the organic EL element according to this embodiment, R ２０１ ~R ２０８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３a group represented by —O—(R ９０４ a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ８０１ a group represented by -COOR ８０２ a halogen atom, a cyano group, or a nitro group; ２０１ and L ２０２ each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, ２０１ and Ar ２０２ are each preferably independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0621] In the organic EL element according to this embodiment, ２０１ and L ２０２ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms; Ar ２０１ and Ar ２０２ are each preferably independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0622] In the organic EL element according to this embodiment, Ar ２０１ and Ar ２０２ are preferably each independently a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.

[0623] In the organic EL element according to this embodiment, the second compound represented by the general formula (2) is preferably a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208), or general formula (209).

[0624]

[0625]

[0626]

[0627]

[0628]

[0629]

[0630]

[0631]

[0632]

[0633] (In the general formulas (201) to (209), L ２０１ and Ar ２０１ represents L in the general formula (2). ２０１ and Ar ２０１ is synonymous with R ２０１ ~R ２０８ are each independently R in the general formula (2). ２０１ ~R ２０８ is synonymous with

[0634] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228), or general formula (229).

[0635]

[0636]

[0637]

[0638]

[0639]

[0640]

[0641]

[0642]

[0643]

[0644] (In the general formula (221), the general formula (222), the general formula (223), the general formula (224), the general formula (225), the general formula (226), the general formula (227), the general formula (228) and the general formula (229), R ２０１ and R ２０３ ~R ２０８ are each independently R in the general formula (2). ２０１ and R ２０３ ~R ２０８ is synonymous with L ２０１ and Ar ２０１ respectively represent L in the general formula (2). ２０１ and Ar ２０１ is synonymous with L ２０３ represents L in the general formula (2). ２０１ is synonymous with L ２０３ and L ２０１ are the same or different from each other, Ar ２０３ represents Ar in the general formula (2). ２０１ Ar ２０３ and Ar ２０１ are the same or different from each other.)

[0645] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248), or general formula (249).

[0646]

[0647]

[0648]

[0649]

[0650]

[0651]

[0652]

[0653]

[0654]

[0655] (In the general formula (241), the general formula (242), the general formula (243), the general formula (244), the general formula (245), the general formula (246), the general formula (247), the general formula (248) and the general formula (249), R ２０１ , R ２０２ and R ２０４ ~R ２０８ are each independently R in the general formula (2). ２０１ , R ２０２ and R ２０４ ~R ２０８ is synonymous with L ２０１ and Ar ２０１ respectively represent L in the general formula (2). ２０１ and Ar ２０１ is synonymous with L ２０３ represents L in the general formula (2). ２０１ is synonymous with L ２０３ and L ２０１ are the same or different from each other, Ar ２０３ represents Ar in the general formula (2). ２０１ Ar ２０３ and Ar ２０１ are the same or different from each other.)

[0656] In the second compound represented by the general formula (2), R ２０１ ~R ２０８are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or —Si(R ９０１ ) (R ９０２ ) (R ９０３ ) is preferably a group represented by the formula (I).

[0657] L ２０１ represents a single bond or an unsubstituted arylene group having 6 to 22 ring carbon atoms, and Ar ２０１ is preferably a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.

[0658] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R ２０１ ~R ２０８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or —Si(R ９０１ ) (R ９０２ ) (R ９０３ ) is preferably a group represented by the formula (I).

[0659] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R ２０１ ~R ２０８ is preferably a hydrogen atom.

[0660] In the second compound, all of the groups described as "substituted or unsubstituted" are preferably "unsubstituted" groups.

[0661] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) ２０１ is a substituted or unsubstituted dibenzofuranyl group.

[0662] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) ２０１ is an unsubstituted dibenzofuranyl group.

[0663] In the organic EL element according to this embodiment, for example, the second compound represented by the general formula (2) contains at least one hydrogen atom, and at least one of the hydrogen atoms is deuterium.

[0664] In the organic EL device according to this embodiment, for example, L in the second compound represented by the general formula (2) ２０１ are TEMP-63 to TEMP-68.

[0665]

[0666] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) ２０１ represents at least one group selected from the group consisting of a substituted or unsubstituted anthryl group, a benzanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluoranthenyl group, a benzofluoranthenyl group, and a perylenyl group.

[0667] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) ２０１ is a substituted or unsubstituted fluorenyl group.

[0668] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) ２０１ is a substituted or unsubstituted xanthenyl group.

[0669] In the organic EL device according to this embodiment, for example, Ar in the second compound represented by the general formula (2) ２０１ is a benzoxanthenyl group.

[0670] (Method for Producing Second Compound) The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0671] (Specific Examples of the Second Compound) Specific examples of the second compound include the following compounds, however, the present invention is not limited to these specific examples of the second compound.

[0672]

[0673]

[0674]

[0675]

[0676]

[0677]

[0678]

[0679]

[0680]

[0681]

[0682]

[0683]

[0684]

[0685]

[0686]

[0687]

[0688]

[0689]

[0690]

[0691]

[0692]

[0693]

[0694]

[0695]

[0696]

[0697]

[0698] (First Light-Emitting Compound and Second Light-Emitting Compound) In the organic EL element 1B, it is also preferable that the first light-emitting layer 51 further contains a first light-emitting compound (preferably a fluorescent compound). In the organic EL element 1B, it is also preferable that the second light-emitting layer 52 further contains a second light-emitting compound (preferably a fluorescent compound). When the first light-emitting layer 51 contains a first light-emitting compound and the second light-emitting layer 52 contains a second light-emitting compound, the first light-emitting compound and the second light-emitting compound are the same as or different from each other. Examples of the first light-emitting compound and the second light-emitting compound include the same light-emitting compounds as those exemplified in the organic EL element 1A.

[0699] In one embodiment, the organic EL element 1B contains, as at least one of the first light-emitting compound in the first light-emitting layer 51 and the second light-emitting compound in the second light-emitting layer 52, one or more compounds selected from the group consisting of the compound represented by the general formula (4), the compound represented by the general formula (5), the compound represented by the general formula (6), and the compound represented by the general formula (63a).

[0700] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the formulas is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ａ ) (R ９０２ａ ) (R ９０３ａ a group represented by —O—(R ９０４ａ a group represented by —S—(R ９０５ａ a group represented by —N(R ９０６ａ ) (R ９０７ａ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ａ ~R ９０７ａ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms; R ９０１ａ When two or more R ９０１ａ are the same or different from each other, R ９０２ａ When two or more R ９０２ａ are the same or different from each other, R ９０３ａ When two or more R ９０３ａ are the same or different from each other, R ９０４ａ When two or more R ９０４ａ are the same or different from each other, R ９０５ａ When two or more R ９０５ａ are the same or different from each other, R ９０６ａ When two or more R ９０６ａ are the same or different from each other, R ９０７ａ When two or more R ９０７ａ are the same as or different from each other.

[0701] In one embodiment, the substituent in the term "substituted or unsubstituted" in each of the formulas is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0702] In one embodiment, the substituent in the term "substituted or unsubstituted" in each of the formulas is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0703] In organic EL element 1B, the first light-emitting compound contained in first light-emitting layer 51 is preferably a compound that exhibits emission with a maximum peak wavelength of 500 nm or less, more preferably a compound that exhibits emission with a maximum peak wavelength of 430 nm or more and 480 nm or less. In organic EL element 1B, the first light-emitting compound contained in first light-emitting layer 51 is preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 500 nm or less, more preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.

[0704] In organic EL element 1B, the second light-emitting compound contained in second light-emitting layer 52 is preferably a compound that exhibits emission with a maximum peak wavelength of 500 nm or less, more preferably a compound that exhibits emission with a maximum peak wavelength of 430 nm or more and 480 nm or less. In organic EL element 1B, the second light-emitting compound contained in second light-emitting layer 52 is preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 500 nm or less, more preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.

[0705] In the organic EL element 1B, when the first light-emitting layer 51 contains a first compound and a first light-emitting compound, the first compound is preferably a host material, and the first light-emitting compound is preferably a dopant material.

[0706] In the organic EL element 1B, the triplet energy T １ (H1) and the triplet energy T of the second compound １ (H2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1): T １ (H1)>T １ (H2) ... (Equation 1)

[0707] Triplet-Triple-Annihilation (sometimes referred to as TTA) has been known as a technique for improving the luminous efficiency of organic EL elements. TTA is a mechanism in which triplet excitons collide with other triplet excitons to generate singlet excitons. The TTA mechanism is also sometimes referred to as the TTF mechanism, as described in International Publication No. WO 2010 / 134350.

[0708] The TTF phenomenon will be explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As has been conventionally known, the spin state of these excitons is 25% singlet excitons and 75% triplet excitons. In conventional fluorescent elements, 25% of the singlet excitons emit light when they relax to the ground state, while the remaining 75% of the triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent elements was said to be 25%. Meanwhile, the behavior of triplet excitons generated within organic materials has been theoretically investigated. According to S. M. Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), assuming that higher-order excitons such as quintets immediately return to triplets, triplet excitons (hereinafter referred to as triplet excitons) can be calculated as follows: ３ A ＊ When the density of triplet excitons (hereinafter referred to as triplet excitons) increases, the triplet excitons collide with each other, causing the reaction shown in the following formula: １ A represents the ground state, １ A ＊ represents the lowest excited singlet exciton. ３ A ＊ + ３ A ＊ → (4 / 9) １ A+ (1 / 9) １ A ＊ + (13 / 9) ３ A ＊ That is, 5 ３ A ＊ →4 １ A+1A ＊It is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will convert to singlet excitons. Therefore, the singlet excitons contributing to light are 40%, calculated by adding 75% × (1 / 5) = 15% to the 25% initially generated. In this case, the TTF-derived emission ratio (TTF ratio) of the total luminescence intensity is 15 / 40, or 37.5%. Furthermore, if we assume that singlet excitons are generated by collisions between the 75% of the initially generated triplet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% is obtained by adding 75% × (1 / 2) = 37.5% to the 25% of the initially generated singlet excitons. In this case, the TTF ratio is 37.5 / 62.5 = 60%.

[0709] According to the organic EL device of this embodiment, triplet excitons generated by recombination of holes and electrons in the first light-emitting layer are thought to be less likely to be quenched at the interface between the first light-emitting layer and the organic layer, even if excess carriers are present at the interface between the first light-emitting layer and the organic layer that is in direct contact with the first light-emitting layer. For example, when the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching by excess electrons is thought to occur. On the other hand, when the recombination region is locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching by excess holes is thought to occur. The organic EL device 1B includes at least two light-emitting layers (i.e., a first light-emitting layer 51 and a second light-emitting layer 52) that satisfy a predetermined relationship, and the triplet energy T of the first compound in the first light-emitting layer 51 is １ (H1) and the triplet energy T １By providing the first light-emitting layer 51 and the second light-emitting layer 52 so that (H2) satisfies the relationship of the above mathematical formula (Mathematical Formula 1), triplet excitons generated in the first light-emitting layer 51 migrate to the second light-emitting layer 52 without being quenched by excess carriers, and reverse migration from the second light-emitting layer 52 to the first light-emitting layer 51 can be suppressed. As a result, the TTF mechanism is exhibited in the second light-emitting layer 52, singlet excitons are efficiently generated, and luminous efficiency is improved. In this way, the organic EL device 1B includes, as distinct regions, the first light-emitting layer 51 that mainly generates triplet excitons and the second light-emitting layer 52 that mainly exhibits the TTF mechanism by utilizing the triplet excitons transferred from the first light-emitting layer 51. By using, as the second compound in the second light-emitting layer 52, a compound having a lower triplet energy than the first compound in the first light-emitting layer, thereby providing a difference in triplet energy, luminous efficiency is improved.

[0710] (triplet energy T １ ) Triplet energy T １ The following method can be used to measure the compound to be measured: －５ mol / L or more 10 －４ The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent line was drawn to the rising edge of the phosphorescence spectrum on the short wavelength side, and the wavelength value λ at the intersection of the tangent line and the horizontal axis was determined. ｅｄｇｅ Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the triplet energy T １ Conversion formula (F1): T １ [eV]=1239.85 / λ ｅｄｇｅ

[0711] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corporation. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.

[0712] In the organic EL element 1B, when the first light-emitting layer 51 contains a first compound and a first light-emitting compound, the singlet energy S １ (H1) and the singlet energy S of the first luminescent compound １ (D3) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2): １ (H1)>S １ (D3)...(Equation 2)

[0713] (singlet energy S １ ) Singlet energy S using solution １ The following methods can be used to measure the compound to be measured (sometimes referred to as the solution method). －５ mol / L or more 10 －４A toluene solution of 1000 mol / L or less is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to obtain the singlet energy S １ Calculate the conversion formula (F2): S １ [eV]=1239.85 / λedge. The absorption spectrum measuring device may be, for example, a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0714] A tangent to the fall of the absorption spectrum on the long wavelength side is drawn as follows: When moving along the spectral curve from the longest maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction of longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall of the absorption spectrum on the long wavelength side. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0715] In the organic EL element 1B, when the second light-emitting layer 52 contains a second compound and a second light-emitting compound, the second compound is preferably a host material, and the second light-emitting compound is preferably a dopant material.

[0716] In the organic EL element 1B, when the second light-emitting layer 52 contains a second compound and a second light-emitting compound, the singlet energy S １ (H2) and the singlet energy S of the second luminescent compound １ (D4) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 3): １ (H2)>S １ (D4)...(Equation 3)

[0717] The first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain a phosphorescent material (dopant material). Furthermore, the first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes. Furthermore, the first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain a metal complex.

[0718] (Thickness of the Light-Emitting Layer) The thickness of each of the first light-emitting layer 51 and the second light-emitting layer 52 in the organic EL element 1B is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. When the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity. When the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in driving voltage.

[0719] (Compound Content in Light-Emitting Layer) When the first light-emitting layer 51 contains a first compound and a first light-emitting compound, the contents of the first compound and the first light-emitting compound in the first light-emitting layer 51 are preferably, for example, in the following ranges. The content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the first light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the first compound and the first light-emitting compound in the first light-emitting layer 51 is 100% by mass.

[0720] Note that this embodiment does not exclude the case where the first light-emitting layer 51 contains a material other than the first compound and the first light-emitting compound. The first light-emitting layer 51 may contain only one type of first compound, or may contain two or more types of first compounds. The first light-emitting layer 51 may contain only one type of first light-emitting compound, or may contain two or more types of first light-emitting compounds.

[0721] When the second light-emitting layer 52 contains a second compound and a second light-emitting compound, the contents of the second compound and the second light-emitting compound in the second light-emitting layer 52 are preferably, for example, within the following ranges. The content of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the second light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the second compound and the second light-emitting compound in the second light-emitting layer 52 is 100% by mass.

[0722] Note that this embodiment does not exclude the case where the second light-emitting layer 52 contains a material other than the second compound and the second light-emitting compound. The second light-emitting layer 52 may contain only one type of second compound, or may contain two or more types of second compounds. The second light-emitting layer 52 may contain only one type of second light-emitting compound, or may contain two or more types of second light-emitting compounds.

[0723] In the organic EL element 1B, it is also preferable that the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact with each other.

[0724] In the organic EL element 1B, when "the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact with each other," the layer structure "in which the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact with each other" may include, for example, any of the following modes (LS1), (LS2), and (LS3): (LS1) A mode in which, during the process of vapor-depositing the compound for the first light-emitting layer 51 and the compound for the second light-emitting layer 52, a region in which both the first compound as a host material (hereinafter sometimes referred to as the "first host material") and the second compound as a host material (hereinafter sometimes referred to as the "second host material") are mixed is generated, and this region is present at the interface between the first light-emitting layer 51 and the second light-emitting layer 52. (LS2) An embodiment in which, when the first light-emitting layer 51 and the second light-emitting layer 52 contain a light-emitting compound, a region in which the first host material, the second host material, and the light-emitting compound are mixed is generated during the process of vapor-depositing the compound for the first light-emitting layer 51 and the process of vapor-depositing the compound for the second light-emitting layer 52, and the region is present at the interface between the first light-emitting layer 51 and the second light-emitting layer 52. (LS3) An embodiment in which, when the first light-emitting layer 51 and the second light-emitting layer 52 contain a light-emitting compound, a region made of the light-emitting compound, a region made of the first host material, or a region made of the second host material is generated during the process of vapor-depositing the compound for the first light-emitting layer 51 and the process of vapor-depositing the compound for the second light-emitting layer 52, and the region is present at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

[0725] When the organic EL element 1B includes a third light-emitting layer, it is preferable that the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact with each other, and that the second light-emitting layer 52 and the third light-emitting layer are in direct contact with each other.

[0726] In the organic EL element 1B, when "the second light-emitting layer 52 and the third light-emitting layer are in direct contact with each other," the layer structure "in which the second light-emitting layer 52 and the third light-emitting layer are in direct contact with each other" may include, for example, any of the following modes (LS4), (LS5), and (LS6): (LS4) A mode in which a region in which both the second host material and the third host material (the host material contained in the third light-emitting layer) are mixed is generated during the process of vapor-depositing the compound for the second light-emitting layer 52 and the compound for the third light-emitting layer, and this region is present at the interface between the second light-emitting layer 52 and the third light-emitting layer. (LS5) An embodiment in which, when the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region in which the second host material, the third host material, and the light-emitting compound are mixed is generated during the process of vapor-depositing the compound for the second light-emitting layer 52 and the process of vapor-depositing the compound for the third light-emitting layer, and the region is present at the interface between the second light-emitting layer 52 and the third light-emitting layer. (LS6) An embodiment in which, when the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region made of the light-emitting compound, a region made of the second host material, or a region made of the third host material is generated during the process of vapor-depositing the compound for the second light-emitting layer 52 and the process of vapor-depositing the compound for the third light-emitting layer, and the region is present at the interface between the second light-emitting layer 52 and the third light-emitting layer.

[0727] It is also preferable that the organic EL element 1B further includes an intervening layer. When the organic EL element 1B includes an intervening layer, the intervening layer is preferably disposed between the first light-emitting layer 51 and the second light-emitting layer 52.

[0728] (Intervening Layer) The intervening layer is preferably a non-doped layer. The intervening layer preferably does not contain metal atoms. The intervening layer contains an intervening layer material. The intervening layer material is preferably not a light-emitting compound. The intervening layer material is not particularly limited, but is preferably a material other than a light-emitting compound. Examples of the intervening layer material include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives; and 3) aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives.

[0729] The intervening layer material may be one or both of the first compound contained in the first light-emitting layer 51 and the second compound contained in the second light-emitting layer 52 .

[0730] When the intermediate layer contains multiple intermediate layer materials, the content of each intermediate layer material is preferably 10% by mass or more of the total mass of the intermediate layer. The intermediate layer preferably contains the intermediate layer material in an amount of 60% by mass or more of the total mass of the intermediate layer, more preferably 70% by mass or more of the total mass of the intermediate layer, even more preferably 80% by mass or more of the total mass of the intermediate layer, even more preferably 90% by mass or more of the total mass of the intermediate layer, and even more preferably 95% by mass or more of the total mass of the intermediate layer. The intermediate layer may contain only one type of intermediate layer material, or two or more types. When the intermediate layer contains two or more types of intermediate layer materials, the upper limit of the total content of the two or more intermediate layer materials is 100% by mass. This embodiment does not exclude the inclusion of materials other than the intermediate layer material in the intermediate layer.

[0731] The intervening layer may be composed of a single layer or may be composed of two or more layers laminated together.

[0732] The thickness of the intervening layer is not particularly limited, but is preferably 3 nm to 15 nm, more preferably 5 nm to 10 nm, per layer.

[0733] The configuration of each layer common to the organic EL element 1A and the organic EL element 1B will be further described below.

[0734] (Substrate) The substrate 2 is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate 2. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic vapor deposition film can also be used.

[0735] (Anode) For the anode 3 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 oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of metal materials (e.g., titanium nitride).

[0736] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 mass % to 10 mass % of zinc oxide added to indium oxide. Furthermore, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 mass % to 5 mass % of tungsten oxide and 0.1 mass % to 1 mass % of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like.

[0737] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, and therefore materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0738] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0739] (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) for the cathode 4. 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.

[0740] When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used.

[0741] By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0742] (Hole Injection Layer) The hole injection layer 61 is a layer containing a substance with high hole injection properties. Examples of the substance with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0743] Furthermore, examples of the substance with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). [N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, such as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[0744] Furthermore, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. Examples of such polymer compounds include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Furthermore, a polymer compound to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0745] (Hole Transport Layer) The hole transport layer 62 is a layer containing a substance with high hole transport properties. For the hole transport layer 62, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: NPB), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 －６ cm ２ The material has a hole mobility of 1 / (V·s) or more.

[0746] The hole transport layer 62 may be made of a carbazole derivative such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), or 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or an anthracene derivative such as t-BuDNA, DNA, or DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) or poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.

[0747] However, other substances may be used as long as they have a higher hole-transporting property than an electron-transporting property. Note that the layer containing the substance having a high hole-transporting property may be not only a single layer, but also a stack of two or more layers containing the above-mentioned substances.

[0748] (Electron Transport Layer) The electron transport layer 71 is a layer containing a substance with high electron transport properties. For the electron transport layer 71, 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 can be used. Specifically, low-molecular organic compounds such as Alq and tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq) can be used. ３ ), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ２ ), BAlq, Znq, ZnPBO, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In this embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 －６ cm ２ The electron-transport layer is a substance having an electron mobility of 1 / (V·s) or more. Note that any substance other than those mentioned above may be used as the electron-transport layer as long as it has a higher electron-transporting property than a hole-transporting property. The electron-transport layer may be formed as a single layer or as a stack of two or more layers made of the above-mentioned substances.

[0749] Furthermore, a polymer compound can also be used for the electron transport layer 71. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy), or the like can be used.

[0750] (Electron Injection Layer) The electron injection layer 72 is a layer containing a substance with high electron injection properties. The electron injection layer 72 may contain any of lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ２ For example, alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), can be used. Alternatively, a substance having electron transport properties containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), can be used. In this case, electron injection from the cathode can be performed more efficiently.

[0751] Alternatively, the electron injection layer 72 may be formed using a composite material comprising an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, for example, the materials constituting the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any material that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (TTF) can also be used.

[0752] (Layer Formation Method) The method for forming each layer of the organic EL element of this embodiment is not limited to those specifically mentioned above, but may be any known method such as a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0753] (Film Thickness) The film thickness of each organic layer in the organic EL element of this embodiment is not limited unless specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer in the organic EL element is usually preferably in the range of several nm to 1 μm.

[0754] According to this embodiment, an organic electroluminescence element with an improved life span can be provided.

[0755] Third Embodiment (Electronic Device) An electronic device according to this embodiment is equipped with the organic EL element according to any one of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lighting fixtures.

[0756] [Modifications of the Embodiment] The present invention is not limited to the above-described embodiment, and any modifications, improvements, etc. that can achieve the object of the present invention are included in the present invention.

[0757] For example, the number of light-emitting layers is not limited to one or two, and two or more light-emitting layers may be stacked. When the organic EL element has two or more light-emitting layers, for example, the light-emitting layers other than the light-emitting layers described in the above embodiments may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission by electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has multiple light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem organic EL element in which multiple light-emitting units are stacked via an intervening layer.

[0758] Furthermore, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The barrier layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a barrier layer is disposed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and blocks holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the barrier layer. When the organic EL device includes an electron transport layer, the barrier layer is preferably provided between the light-emitting layer and the electron transport layer. When a barrier layer is disposed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and blocks electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the barrier layer. When the organic EL device includes a hole transport layer, the barrier layer is preferably provided between the light-emitting layer and the hole transport layer. Furthermore, the barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. The blocking layer prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the blocking layer (for example, the electron transport layer and the hole transport layer).The light-emitting layer and the blocking layer are preferably in contact with each other.

[0759] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope of achieving the object of the present invention.

[0760] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples. <Compound> The structure of the compound represented by general formula (100A) used in the production of the organic EL device according to the examples is shown below.

[0761]

[0762]

[0763]

[0764]

[0765]

[0766]

[0767]

[0768]

[0769] The structures of the comparative compounds used in the production of the organic EL devices according to the comparative examples are shown below.

[0770]

[0771]

[0772] The structures of other compounds used in the organic EL devices according to the examples and comparative examples are shown below.

[0773]

[0774]

[0775]

[0776] <Preparation of Organic EL Device (1)> Organic EL devices were prepared as follows and evaluated.

[0777] Example 1 A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (indium tin oxide) transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and compound HIL-1 was first vapor-deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a 5 nm thick hole injection layer (HI). Following the formation of the hole injection layer, compound HTL-1 was vapor-deposited to form a first hole transport layer with a film thickness of 80 nm. Following the formation of the first hole transport layer, compound EBL-1 was vapor-deposited to form a second hole transport layer (also referred to as an electron blocking layer) with a film thickness of 10 nm. On the second hole-transporting layer, compound BH1-1 as a first compound and compound BD-1 as a first luminescent compound were co-deposited such that the proportion of compound BD-1 was 2% by mass, thereby forming a first luminescent layer with a thickness of 12.5 nm. On the first luminescent layer, compound BH-2 as a second compound and compound BD-1 as a second luminescent compound were co-deposited such that the proportion of compound BD-1 was 2% by mass, thereby forming a second luminescent layer with a thickness of 12.5 nm. On the second luminescent layer, compound aET-1 was deposited by vapor deposition to form a first electron-transporting layer (also referred to as a hole-blocking layer) with a thickness of 10 nm. On the first electron-transporting layer, compound bET-1 was deposited by vapor deposition to form a second electron-transporting layer with a thickness of 15 nm. On the second electron-transporting layer, LiF was deposited by vapor deposition to form an electron-injecting layer with a thickness of 1 nm. On the electron-injecting layer, metal Al was deposited by vapor deposition to form a cathode with a thickness of 80 nm. The device configuration of Example 1 is shown in outline as follows: ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-1:BD-1(12.5,98%:2%) / BH-2:BD-1(12.5,98%:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate film thickness (unit: nm). The percentage numbers in parentheses (98%:2%) indicate the proportions (mass %) of Compound BH1-1 or Compound BH-2 and Compound BD-1 in the first or second emitting layer.

[0778] Example 2 An organic EL device of Example 2 was fabricated in the same manner as in Example 1, except that the first compound in the first emitting layer was changed to a compound shown in Table 1.

[0779] [Comparative Examples 1, 2, and 3] The organic EL elements of Comparative Examples 1, 2, and 3 were fabricated in the same manner as in Example 1, except that the first compound in the first emitting layer was changed to a compound shown in Table 1.

[0780] <Evaluation of Organic EL Devices (1)> The organic EL devices fabricated in Examples 1 and 2 and Comparative Examples 1, 2, and 3 were evaluated as follows. The evaluation results are shown in Table 1.

[0781] Lifetime (LT95) The obtained organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hour)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0782]

[0783] <Preparation of Organic EL Device (2)> An organic EL device was prepared as follows and evaluated.

[0784] Example 3 A 25 mm × 75 mm × 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (indium tin oxide) transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HTL-2 and compound HIL-2 were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The proportion of compound HTL-2 in this hole injection layer was 90% by mass, and the proportion of compound HIL-2 was 10% by mass. Following the formation of the hole injection layer, compound HTL-2 was vapor-deposited to form a first hole transport layer with a film thickness of 85 nm. Following the formation of the first hole-transporting layer, compound EBL-2 was evaporated to form a second hole-transporting layer (also referred to as an electron blocking layer) with a thickness of 5 nm. On the second hole-transporting layer, compound BH1-1 as the first compound and compound BD-2 as the first light-emitting compound were co-evaporated so that the proportion of compound BD-2 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 10 nm. On the first light-emitting layer, compound BH-3 as the second compound and compound BD-2 as the second light-emitting compound were co-evaporated so that the proportion of compound BD-2 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 10 nm. On the second light-emitting layer, compound aET-2 was evaporated to form a first electron-transporting layer (also referred to as a hole-blocking layer) with a thickness of 5 nm. On the first electron-transporting layer, compound bET-2 and compound Liq were co-evaporated to form a second electron-transporting layer with a thickness of 25 nm. The proportion of the compound bET-2 in this second electron transport layer was 50% by mass, and the proportion of the compound Liq was 50% by mass. Liq is an abbreviation for (8-quinolinolato)lithium. The compound Liq 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. The device configuration of Example 3 is schematically shown as follows:ITO(130) / HTL-2:HIL-2(10,90%:10%) / HTL-2(85) / EBL-2(5) / BH1-1:BD-2(10,98%:2%) / BH-3:BD-2(10,98%:2%) / aET-2(5) / bET-2:Liq(25,50%:50%) / Liq(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the figures expressed as percentages (90%:10%) indicate the proportions (mass%) of compound HTL-2 and compound HIL-2 in the hole-injection layer, the figures expressed as percentages (98%:2%) indicate the proportions (mass%) of compound BH1-1 or BH-3 and compound BD-2 in the first emitting layer or second emitting layer, and the figures expressed as percentages (50%:50%) indicate the proportions (mass%) of compound bET-2 and compound Liq in the second electron-transport layer.

[0785] [Examples 4, 5, 6, 7, 8, 9, 10, 11, and 12] The organic EL devices of Examples 4, 5, 6, 7, 8, 9, 10, 11, and 12 were fabricated in the same manner as in Example 3, except that the first compound in the first emitting layer was changed to a compound shown in Table 2.

[0786] <Evaluation of Organic EL Devices (2)> The following evaluations were carried out on the organic EL devices fabricated in Examples 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12. The evaluation results are shown in Table 2.

[0787] Lifetime (LT95) The obtained organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hour)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0788]

[0789] <Preparation of Organic EL Device (3)> Organic EL devices were prepared as follows and evaluated.

[0790] Example 13 A 25 mm × 75 mm × 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (indium tin oxide) transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and compound HIL-1 was first vapor-deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a 5 nm thick hole injection layer (HI). Following the formation of the hole injection layer, compound HTL-1 was vapor-deposited to form a first hole transport layer with a film thickness of 80 nm. Following the formation of the first hole transport layer, compound EBL-1 was vapor-deposited to form a second hole transport layer (also referred to as an electron blocking layer) with a film thickness of 10 nm. On the second hole-transporting layer, compound BH1-7 as a first compound and compound BD-1 as a first luminescent compound were co-deposited such that the proportion of compound BD-1 was 2% by mass, thereby forming a first luminescent layer with a thickness of 12.5 nm. On the first luminescent layer, compound BH-2 as a second compound and compound BD-1 as a second luminescent compound were co-deposited such that the proportion of compound BD-1 was 2% by mass, thereby forming a second luminescent layer with a thickness of 12.5 nm. On the second luminescent layer, compound aET-1 was deposited by vapor deposition to form a first electron-transporting layer (also referred to as a hole-blocking layer) with a thickness of 10 nm. On the first electron-transporting layer, compound bET-1 was deposited by vapor deposition to form a second electron-transporting layer with a thickness of 15 nm. On the second electron-transporting layer, LiF was deposited by vapor deposition to form an electron-injecting layer with a thickness of 1 nm. On the electron-injecting layer, metal Al was deposited by vapor deposition to form a cathode with a thickness of 80 nm. The device configuration of Example 13 is shown in outline as follows: ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-7:BD-1(12.5,98%:2%) / BH-2:BD-1(12.5,98%:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate film thickness (unit: nm). The numbers in parentheses (98%:2%) indicate the proportions (mass %) of Compound BH1-7 or Compound BH-2 and Compound BD-1 in the first or second emitting layer.

[0791] [Examples 14, 15, 16, 17, 18, 19, and 20] The organic EL devices of Examples 14, 15, 16, 17, 18, 19, and 20 were fabricated in the same manner as in Example 13, except that the first compound in the first emitting layer was changed to a compound shown in Table 3.

[0792] Comparative Example 4 The organic EL device of Comparative Example 4 was fabricated in the same manner as in Example 13, except that the first compound in the first emitting layer was changed to a compound shown in Table 3.

[0793] <Evaluation of Organic EL Devices (3)> The organic EL devices fabricated in Examples 13, 14, 15, 16, 17, 18, 19, and 20, and Comparative Example 4 were evaluated as follows. The evaluation results are shown in Table 3.

[0794] ・CIE1931 chromaticity Current density is 10.00mA / cm ２ The CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the element so as to satisfy the following equation were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0795] Lifetime (LT95) The obtained organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 3 shows the measured LT95 values ​​for each example (Examples 13 to 20 and Comparative Example 4), as well as the "LT95 (relative value)" (unit: %) calculated based on the following formula (Math 1X): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 4) × 100 (Math 1X)

[0796]

[0797] <Preparation of Organic EL Device (4)> An organic EL device was prepared as follows and evaluated.

[0798] Example 21 A 25 mm × 75 mm × 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (indium tin oxide) transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with transparent electrode lines was attached to a substrate holder in a vacuum deposition apparatus, and first, compound HTL-2 and compound HIL-2 were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a film thickness of 10 nm. The proportion of compound HTL-2 in this hole injection layer was 90% by mass, and the proportion of compound HIL-2 was 10% by mass. Following the formation of the hole injection layer, compound HTL-2 was deposited by vapor deposition to form a first hole transport layer with a film thickness of 85 nm. Following the formation of the first hole-transporting layer, compound EBL-2 was evaporated to form a second hole-transporting layer (also referred to as an electron blocking layer) with a thickness of 5 nm. On the second hole-transporting layer, compound BH1-7 as a first compound and compound BD-3 as a first light-emitting compound were co-evaporated so that the proportion of compound BD-3 was 2% by mass, thereby forming a first light-emitting layer with a thickness of 10 nm. On the first light-emitting layer, compound BH-3 as a second compound and compound BD-3 as a second light-emitting compound were co-evaporated so that the proportion of compound BD-3 was 2% by mass, thereby forming a second light-emitting layer with a thickness of 10 nm. On the second light-emitting layer, compound aET-2 was evaporated to form a first electron-transporting layer (also referred to as a hole-blocking layer) with a thickness of 5 nm. On the first electron-transporting layer, compound bET-2 and compound Liq were co-evaporated to form a second electron-transporting layer with a thickness of 25 nm. The proportion of the compound bET-2 in this second electron transport layer was 50% by mass, and the proportion of the compound Liq was 50% by mass. The compound Liq was vapor-deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Metal Al was vapor-deposited on the electron injection layer to form a cathode with a thickness of 80 nm. The device configuration of Example 21 is schematically shown as follows.ITO(130) / HTL-2:HIL-2(10,90%:10%) / HTL-2(85) / EBL-2(5) / BH1-7:BD-3(10,98%:2%) / BH-3:BD-3(10,98%:2%) / aET-2(5) / bET-2:Liq(25,50%:50%) / Liq(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the figures expressed as percentages (90%:10%) indicate the proportions (mass%) of Compound HTL-2 and Compound HIL-2 in the hole-injection layer, the figures expressed as percentages (98%:2%) indicate the proportions (mass%) of Compound BH1-7 or BH-3 and Compound BD-3 in the first emitting layer or second emitting layer, and the figures expressed as percentages (50%:50%) indicate the proportions (mass%) of Compound bET-2 and Compound Liq in the second electron-transport layer.

[0799] Example 22 An organic EL device of Example 22 was produced in the same manner as in Example 21, except that the first compound in the first emitting layer was changed to a compound shown in Table 4.

[0800] Comparative Example 5 The organic EL device of Comparative Example 5 was fabricated in the same manner as in Example 21, except that the first compound in the first emitting layer was changed to a compound shown in Table 4.

[0801] <Evaluation of Organic EL Devices (4)> The organic EL devices fabricated in Examples 21 and 22 and Comparative Example 5 were evaluated as follows. The evaluation results are shown in Table 4.

[0802] ・CIE1931 chromaticity Current density is 10.00mA / cm ２ The CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the element so as to satisfy the following equation were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0803] Lifetime (LT95) The obtained organic EL element was subjected to a current density of 50 mA / cm ２A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 4 shows the measured LT95 values ​​for each example (Examples 21 and 22, and Comparative Example 5), as well as the "LT95 (relative value)" (unit: %) calculated based on the following formula (Math 2X): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 5) × 100 (Math 2X)

[0804]

[0805] <Preparation of Organic EL Device (5)> An organic EL device was prepared as follows and evaluated.

[0806] [Examples 23, 24, and 25] The organic EL devices of Examples 23, 24, and 25 were fabricated in the same manner as in Example 1, except that the first compound in the first emitting layer was changed to a compound shown in Table 5.

[0807] Comparative Example 6 The organic EL device of Comparative Example 6 was fabricated in the same manner as in Example 1, except that the first compound in the first emitting layer was changed to a compound shown in Table 5.

[0808] <Evaluation of Organic EL Devices (5)> The organic EL devices fabricated in Examples 23, 24, and 25 and Comparative Example 6 were evaluated as follows. The evaluation results are shown in Table 5.

[0809] Lifetime (LT95) The obtained organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 5 shows the measured LT95 values ​​for each example (Examples 23 to 25 and Comparative Example 6), as well as the "LT95 (relative value)" (unit: %) calculated based on the following formula (Equation 3X): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 6) × 100 (Equation 3X)

[0810]

[0811] <Preparation of Organic EL Device (6)> An organic EL device was prepared as follows and evaluated.

[0812] Example 26 The organic EL device of Example 26 was produced in the same manner as in Example 3, except that the first compound in the first emitting layer was changed to a compound shown in Table 6.

[0813] Comparative Example 7 The organic EL device of Comparative Example 7 was fabricated in the same manner as in Example 3, except that the first compound in the first emitting layer was changed to a compound shown in Table 6.

[0814] <Evaluation of Organic EL Devices (6)> The organic EL devices fabricated in Example 26 and Comparative Example 7 were evaluated as follows. The evaluation results are shown in Table 6.

[0815] Lifetime (LT95) The obtained organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 6 shows the measured LT95 values ​​for each example (Example 26 and Comparative Example 7), as well as the "LT95 (relative value)" (unit: %) calculated based on the following formula (Math 4X): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 7) × 100 (Math 4X)

[0816]

[0817] <Preparation of Organic EL Device (7)> ​​An organic EL device was prepared as follows and evaluated.

[0818] Example 27 An organic EL device of Example 27 was produced in the same manner as in Example 21, except that the first compound in the first emitting layer was changed to a compound shown in Table 7.

[0819] Comparative Example 8 The organic EL device of Comparative Example 8 was produced in the same manner as in Example 21, except that the first compound in the first emitting layer was changed to a compound shown in Table 7.

[0820] <Evaluation of Organic EL Devices (7)> ​​The organic EL devices fabricated in Example 27 and Comparative Example 8 were evaluated as follows. The evaluation results are shown in Table 7.

[0821] Lifetime (LT95) The obtained organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 7 shows the measured LT95 values ​​for each example (Example 27 and Comparative Example 8), as well as the "LT95 (relative value)" (unit: %) calculated based on the following formula (Math. 5X): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 8) × 100 (Math. 5X)

[0822]

[0823] <Compound evaluation> (triplet energy T １ The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to prepare a solution, and this solution was placed in a quartz cell to serve as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent was drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. ｅｄｇｅ Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the triplet energy T １ The results are shown in Tables 1 and 2. The triplet energy T １ Depending on the measurement conditions, an error of about 0.02 eV may occur. １ [eV]=1239.85 / λ ｅｄｇｅ

[0824] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence was measured using an F-4500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation.

[0825] (singlet energy S １ A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). A tangent line was drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis was substituted into the following conversion formula (F2) to obtain the singlet energy S １ The results are shown in Tables 1 and 2. Conversion formula (F2): S １ [eV]=1239.85 / λedge A spectrophotometer manufactured by Hitachi (device name: U3310) was used as the absorption spectrum measuring device.

[0826] A tangent to the fall of the absorption spectrum on the long wavelength side is drawn as follows: When moving along the spectral curve from the longest maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction of longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall of the absorption spectrum on the long wavelength side. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0827] (Maximum Peak Wavelength of Compound) The maximum peak wavelength λ of a compound was measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). In this example, the emission spectrum was measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measurement device is not limited to the device used here. The peak wavelength of the emission spectrum at which the emission intensity was maximum was defined as the maximum peak wavelength λ. The maximum peak wavelength λ of compound BD-1 was 452 nm. The maximum peak wavelength λ of compound BD-2 was 455 nm. The maximum peak wavelength λ of compound BD-3 was 457 nm.

[0828] <Synthesis of Compounds> [Synthesis Example 1: Synthesis of Compound BH1-1] Compound BH1-1 was synthesized according to the following synthesis route.

[0829]

[0830] (Synthesis of Compound BH1-1) Under an argon atmosphere, 11.4 g (41.8 mmol) of Intermediate 1-A, 5.0 g (17.4 mmol) of Intermediate 1-B, 0.99 g (1.4 mmol) of dichlorobisammonium palladium (2), 21.8 ml (43.6 mmol) of a 2 M aqueous sodium carbonate solution, and 350 ml of 1,2-dimethoxyethane were placed in a flask and heated with stirring at 73°C for 8 hours. After stirring, the mixture was cooled to room temperature (25°C), and the solvent was distilled off. The resulting solid was purified by silica gel column chromatography to obtain 2.0 g (yield 22%) of a white solid. LC-MS analysis (liquid chromatography mass spectrometry) identified the white solid as Compound BH1-1.

[0831] Synthesis Example 2: Synthesis of Compound BH1-2 Compound BH1-2 was synthesized according to the following synthesis route.

[0832]

[0833] (Synthesis of Intermediate 2-C) Intermediate 2-C was synthesized from Intermediate 2-A in two steps using a synthetic method similar to that described in WO 2007 / 114358, yielding 9.2 g of a white solid (total yield 64%). LC-MS analysis identified the white solid as Intermediate 2-C.

[0834]

[0835] (Synthesis of Compound BH1-2) Compound BH1-2 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C was used instead of Intermediate 1-A, to obtain 0.32 g (yield 39%) of a white solid. LC-MS analysis identified the white solid as Compound BH1-2.

[0836] Synthesis Example 3: Synthesis of Compound BH1-3 Compound BH1-3 was synthesized according to the following synthesis route.

[0837]

[0838] (Synthesis of Intermediate 3-C) Intermediate 3-C was synthesized in the same manner as in the synthesis of Compound BH1-1, except that Intermediate 3-A and Intermediate 3-B were used instead of Intermediate 1-A and Intermediate 1-B in the synthesis of Compound BH1-1, to obtain 3.4 g of a white solid (yield 38%). LC-MS analysis identified the white solid as Intermediate 3-C.

[0839]

[0840] (Synthesis of Compound BH1-3) Compound BH1-3 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C and Intermediate 3-C were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 1.1 g of a white solid (yield 39%). LC-MS analysis identified the white solid as Compound BH1-3.

[0841] Synthesis Example 4: Synthesis of compound BH1-4 Compound BH1-4 was synthesized according to the following synthesis route.

[0842]

[0843] (Synthesis of Compound BH1-4) Compound BH1-4 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C and Intermediate 4-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 0.7 g of a pale yellow solid (yield 62%). LC-MS analysis identified the pale yellow solid as Compound BH1-4.

[0844] Synthesis Example 5: Synthesis of Compound BH1-5 Compound BH1-5 was synthesized according to the following synthesis route.

[0845]

[0846] (Synthesis of Compound BH1-5) Compound BH1-5 was synthesized in the same manner as Compound BH1-1, except that Intermediate 4-A and Intermediate 5-A were used instead of Intermediate 1-A and Intermediate 1-B. 1.3 g of a pale yellow solid was obtained (yield: 48%). LC-MS analysis identified the pale yellow solid as Compound BH1-5.

[0847] Synthesis Example 6: Synthesis of compound BH1-6 Compound BH1-6 was synthesized according to the following synthesis route.

[0848]

[0849] (Synthesis of Compound BH1-6) Compound BH1-6 was synthesized in the same manner as Compound BH1-1, except that Intermediate 3-A and Intermediate 5-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 0.2 g of a pale yellow solid (yield 19%). LC-MS analysis identified the pale yellow solid as Compound BH1-6.

[0850] Synthesis Example 7 Synthesis of Compound BH1-7 Compound BH1-7 was synthesized according to the following synthesis route.

[0851]

[0852] (Synthesis of Compound BH1-7) Compound BH1-7 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C and Intermediate 7-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 2.1 g of a white solid (yield 77%). LC-MS analysis identified the white solid as Compound BH1-7.

[0853] Synthesis Example 8: Synthesis of compound BH1-8 Compound BH1-8 was synthesized according to the following synthesis route.

[0854]

[0855] (Synthesis of Compound BH1-8) Compound BH1-8 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C and Intermediate 8-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 0.9 g of a white solid (yield 51%). LC-MS analysis identified the white solid as Compound BH1-8.

[0856] Synthesis Example 9: Synthesis of Compound BH1-9 Compound BH1-9 was synthesized according to the following synthesis route.

[0857]

[0858] (Synthesis of Compound BH1-9) Compound BH1-9 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C and Intermediate 9-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 1.7 g of a white solid (yield 46%). LC-MS analysis identified the white solid as Compound BH1-9.

[0859] Synthesis Example 10: Synthesis of Compound BH1-10 Compound BH1-10 was synthesized according to the following synthesis route.

[0860]

[0861] (Synthesis of Compound BH1-10) Compound BH1-10 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C and Intermediate 10-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 1.3 g of a white solid (yield 63%). LC-MS analysis identified the white solid as Compound BH1-10.

[0862] Synthesis Example 11: Synthesis of compound BH1-11 Compound BH1-11 was synthesized according to the following synthesis route.

[0863]

[0864] (Synthesis of Intermediate 11-A) The same synthesis method as for Compound BH1-1 was used, except that Intermediate 7-A was used instead of Intermediate 1-B in the synthesis of Compound BH1-1, to obtain 2.3 g of a pale yellow solid (yield: 56%). LC-MS analysis identified the pale yellow solid as Intermediate 11-A.

[0865] (Synthesis of Compound BH1-11) Under an argon atmosphere, 5.0 g (11.3 mmol) of Intermediate 11-A and 100 ml of ortho-dichlorobenzene were placed in a flask and completely dissolved with stirring at room temperature. 50 ml of benzene-d6 was then added and the mixture was stirred at 10°C for 5 minutes. 1.99 ml (22.5 mmol) of trifluoromethanesulfonic acid was then added and the mixture was stirred at 10°C for 2 hours. 200 ml of heavy water was then added and the mixture was stirred for an additional 15 minutes. After stirring, the aqueous layer was removed and the remaining organic layer was concentrated. The resulting solid was purified by silica gel column chromatography to obtain 3.0 g of a pale yellow solid (yield 58%). LC-MS analysis identified the pale yellow solid as Compound BH1-11.

[0866] Synthesis Example 12: Synthesis of compound BH1-12 Compound BH1-12 was synthesized according to the following synthesis route.

[0867]

[0868] (Synthesis of Intermediate 12-C) Under an argon atmosphere, 25.0 g (144.0 mmol) of Intermediate 12-A, 31.5 g (158.0 mmol) of Intermediate 12-B, 70.1 g (215.0 mmol) of cesium carbonate, and 300 ml of N,N-dimethylformamide were placed in a flask and heated with stirring at 130°C for 10 hours. After cooling to room temperature (25°C), the reaction solution was concentrated, and the resulting residue was purified by silica gel column chromatography to obtain 34.0 g (yield 65%) of a white solid. LC-MS analysis identified the white solid as Intermediate 12-C.

[0869] (Synthesis of Intermediate 12-D) Under an argon atmosphere, 34.0 g (94.0 mmol) of Intermediate 12-C, 2.1 g (2.8 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), 25.8 g (187.0 mmol) of potassium carbonate, and 940 ml of N,N-dimethylformamide were placed in a flask and heated with stirring at 130°C for 10 hours. After cooling to room temperature (25°C), the reaction solution was concentrated, and the resulting residue was purified by silica gel column chromatography to obtain 15.6 g (yield 59%) of a white solid. LC-MS analysis identified the white solid as Intermediate 12-D.

[0870] (Synthesis of Intermediate 12-E) Under an argon atmosphere, 15.6 g (55.2 mmol) of Intermediate 12-D and 150 ml of dichloromethane were placed in a flask. After the solution was cooled to 0°C, 71.7 ml (71.7 mmol) of a 1 M solution of boron tribromide in dichloromethane was added dropwise to the system, and the mixture was stirred for 1 hour. After stirring for an additional 6 hours while returning the temperature to room temperature (25°C), ice water was added to the reaction solution. After thorough stirring, the aqueous layer was removed, and the remaining organic layer was concentrated. The residue was purified by silica gel column chromatography to obtain 11.6 g of a white solid (yield 78%). LC-MS analysis identified the white solid as Intermediate 12-E.

[0871] (Synthesis of Intermediate 12-F) Under an argon atmosphere, 11.6 g (43.2 mmol) of Intermediate 12-E and 215 ml of dichloromethane were placed in a flask. After the solution was cooled to 0°C, 4.4 ml (56.1 mmol) of pyridine was added dropwise to the system, followed by 9.2 ml (56.1 mmol) of trifluoromethanesulfonic anhydride, and the mixture was stirred for 1 hour. After stirring for an additional 6 hours while returning to room temperature (25°C), ice water was added to the reaction solution. After thorough stirring, the aqueous layer was removed, and the remaining organic layer was concentrated. The residue was purified by silica gel column chromatography to obtain 12.5 g of a white solid (72% yield). LC-MS analysis identified the white solid as Intermediate 12-F.

[0872] (Synthesis of Intermediate 12-H) The same synthesis method as for Compound BH1-1 was used, except that Intermediate 12-F and Intermediate 12-G were used instead of Intermediate 1-A and Intermediate 1-B in the synthesis of Compound BH1-1, to obtain 6.5 g of a white solid (yield 63%). LC-MS analysis identified the white solid as Intermediate 12-H.

[0873] (Synthesis of Intermediate 12-I) Under an argon atmosphere, 6.5 g (19.8 mmol) of Intermediate 12-H, 10.0 g (39.5 mmol) of bis(pinacolato)diboron, 0.09 g (0.4 mmol) of palladium(II) acetate, 0.75 g (1.6 mmol) of XPhos, 5.82 g (59.3 mmol) of potassium acetate, and 100 mL of 1,4-dioxane were placed in a flask and stirred at 100°C for 7 hours. After stirring, the mixture was cooled to room temperature. After cooling, the organic layer was washed with saturated brine and then dried by adding sodium sulfate. After drying, the mixture was filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to obtain 2.8 g of a white solid (yield 49%). LC-MS analysis identified the white solid as Intermediate 12-I.

[0874]

[0875] (Synthesis of Compound BH1-12) Compound BH1-12 was synthesized in the same manner as Compound BH1-1, except that Intermediate 12-I and Intermediate 2-B were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 0.8 g of a pale yellow solid (yield 63%). LC-MS analysis identified the pale yellow solid as Compound BH1-12.

[0876] Synthesis Example 13: Synthesis of compound BH1-13 Compound BH1-13 was synthesized according to the following synthesis route.

[0877]

[0878] (Synthesis of Intermediate 13-B) The synthesis was carried out in the same manner as for Compound BH1-1, except that Intermediate 12-I and Intermediate 13-A were used instead of Intermediate 1-A and Intermediate 1-B in the synthesis of Compound BH1-1, to obtain 1.3 g of a pale yellow solid (yield: 53%). LC-MS analysis identified the pale yellow solid as Intermediate 13-B.

[0879]

[0880] (Synthesis of Compound BH1-13) Compound BH1-13 was synthesized in the same manner as Compound BH1-11, except that Intermediate 13-B was used instead of Intermediate 11-A, to obtain 0.4 g (yield 36%) of a pale yellow solid. LC-MS analysis identified the pale yellow solid as Compound BH1-13.

[0881] Synthesis Example 14: Synthesis of compound BH1-14 Compound BH1-14 was synthesized according to the following synthesis route.

[0882]

[0883] (Synthesis of Compound BH1-14) Compound BH1-14 was synthesized in the same manner as Compound BH1-1, except that Intermediate 2-C and Intermediate 15-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 3.6 g of a pale yellow solid (yield 71%). LC-MS analysis identified the pale yellow solid as Compound BH1-14.

[0884] Synthesis Example 15: Synthesis of compound BH1-15 Compound BH1-15 was synthesized according to the following synthesis route.

[0885]

[0886] (Synthesis of Intermediate 15-A) The same synthesis method as for Compound BH1-1 was used, except that Intermediate 14-A was used instead of Intermediate 1-B in the synthesis of Compound BH1-1, to obtain 3.6 g of a pale yellow solid (yield 71%). LC-MS analysis identified the pale yellow solid as Intermediate 15-A.

[0887]

[0888] (Synthesis of Compound BH1-15) Compound BH1-15 was synthesized in the same manner as Compound BH1-11, except that Intermediate 15-A was used instead of Intermediate 11-A, to obtain 0.7 g of a pale yellow solid (yield 41%). LC-MS analysis identified the pale yellow solid as Compound BH1-15.

[0889] Synthesis Example 16: Synthesis of compound BH1-16 Compound BH1-16 was synthesized according to the following synthesis route.

[0890]

[0891] (Synthesis of Intermediate 16-G) Intermediate 16-G was synthesized in the same manner as in the synthesis of Intermediate 12-I, except that Intermediate 16-A was used instead of Intermediate 12-A in the series of syntheses of Intermediate 12-I using Intermediate 12-A as the starting material, to obtain 2.4 g of a pale yellow solid (total yield (7 steps) 9%). LC-MS analysis identified the pale yellow solid as Intermediate 16-G.

[0892]

[0893] (Synthesis of Compound BH1-16) Compound BH1-16 was synthesized in the same manner as Compound BH1-1, except that Intermediate 16-G and Intermediate 2-B were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 1.7 g of a pale yellow solid (yield: 58%). LC-MS analysis identified the pale yellow solid as Compound BH1-16.

[0894] Synthesis Example 17: Synthesis of compound BH1-17 Compound BH1-17 was synthesized according to the following synthesis route.

[0895]

[0896] (Synthesis of Intermediate 17-A) Intermediate 17-A was synthesized in the same manner as Intermediate 13-B, except that Intermediate 16-G was used instead of Intermediate 12-I, to obtain 2.4 g of a pale yellow solid (total yield (7 steps) 9%). LC-MS analysis identified the pale yellow solid as Intermediate 17-A.

[0897]

[0898] (Synthesis of Compound BH1-17) Compound BH1-17 was synthesized in the same manner as Compound BH1-11, except that Intermediate 17-A was used instead of Intermediate 11-A, to obtain 0.7 g of a pale yellow solid (yield 44%). LC-MS analysis identified the pale yellow solid as Compound BH1-17.

[0899] Synthesis Example 18: Synthesis of compound BH1-18 Compound BH1-18 was synthesized according to the following synthesis route.

[0900]

[0901] (Synthesis of Compound BH1-18) Compound BH1-18 was synthesized in the same manner as Compound BH1-11, except that Intermediate 18-A was used instead of Intermediate 11-A, to obtain 0.5 g of a pale yellow solid (yield 24%). LC-MS analysis identified the pale yellow solid as Compound BH1-18.

[0902] Synthesis Example 19: Synthesis of compound BH1-19 Compound BH1-19 was synthesized according to the following synthesis route.

[0903]

[0904] (Synthesis of Compound BH1-19) Compound BH1-19 was synthesized in the same manner as Compound BH1-1, except that Intermediate 19-A and Intermediate 5-A were used instead of Intermediate 1-A and Intermediate 1-B, to obtain 0.9 g of a pale yellow solid (yield 47%). LC-MS analysis identified the pale yellow solid as Compound BH1-19.

[0905] Synthesis Example 20: Synthesis of compound BH1-20 Compound BH1-20 was synthesized according to the following synthesis route.

[0906]

[0907] (Synthesis of Intermediate 20-B) Intermediate 20-B was synthesized in the same manner as Intermediate 12-F, except that Intermediate 20-A was used instead of Intermediate 12-E, to obtain 21.3 g of a white solid (yield: 73%). LC-MS analysis identified the white solid as Intermediate 20-B.

[0908] (Synthesis of Intermediate 20-D) The same synthesis method as for Compound BH1-1 was used, except that Intermediate 20-B and Intermediate 20-C were used instead of Intermediate 1-A and Intermediate 1-B in the synthesis of Compound BH1-1, to obtain 19.3 g of a white solid (yield 87%). LC-MS analysis identified the white solid as Intermediate 20-D.

[0909] (Synthesis of Intermediate 20-E) Under an argon atmosphere, 28.1 g of (methoxymethyl)triphenylphosphonium chloride and 130 ml of tetrahydrofuran were placed in a flask and stirred for 5 minutes. Then, 82 ml of a 1 mol / L solution of potassium tert-butoxide in tetrahydrofuran was added, and the mixture was stirred at room temperature for 1.5 hours. A solution of 21.1 g of Intermediate 20-D dissolved in 342 ml of tetrahydrofuran was then added to the system, and the mixture was stirred at room temperature for 3 hours. The precipitated solid was then filtered, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography to obtain 22.5 g of a white solid (yield 98%). This white solid was identified as Intermediate 20-E by LC-MS analysis.

[0910] (Synthesis of Intermediate 20-F) Under an argon atmosphere, 22.5 g of Intermediate 20-E and 684 ml of dichloromethane were placed in a flask and stirred at 0°C for 5 minutes. Then, 7 ml of methanesulfonic acid was added and the mixture was stirred at 0°C for 3 hours. The mixture was then washed with a saturated aqueous solution of sodium bicarbonate, the aqueous layer was removed, and the organic layer was concentrated. The resulting residue was purified by silica gel column chromatography to obtain 9.4 g of a white solid (yield 45%). LC-MS analysis identified the white solid as Intermediate 20-F.

[0911] (Synthesis of Intermediate 20-G) Intermediate 20-G was synthesized in the same manner as Intermediate 12-I, except that Intermediate 20-F was used instead of Intermediate 12-H, to obtain 5.7 g of a white solid (yield: 41%). LC-MS analysis identified the white solid as Intermediate 20-G.

[0912] (Synthesis of Intermediate 20-I) The same synthesis method as for Compound BH1-1 was used, except that Intermediate 20-G and Intermediate 20-H were used instead of Intermediate 1-A and Intermediate 1-B in the synthesis of Compound BH1-1, to obtain 1.9 g of a pale yellow solid (yield 25%). LC-MS analysis identified the pale yellow solid as Intermediate 20-I.

[0913]

[0914] (Synthesis of Compound BH1-20) Compound BH1-20 was synthesized in the same manner as Compound BH1-11, except that Intermediate 20-I was used instead of Intermediate 11-A in the synthesis of Compound BH1-11, to obtain 0.2 g of a pale yellow solid (yield 43%). LC-MS analysis identified the pale yellow solid as Compound BH1-20.

[0915] DESCRIPTION OF THE REFERENCE NUMERALS 1A, 1B... organic EL...

Claims

1. A compound represented by the following general formula (1A): 【Chemistry 1】 (In the general formula (1A), one of R 6 , R 7 , R 11 , and R 12 is a group represented by general formula (1B) above; R １ R 1 to R 5, R 8 to R 10, and R 6 , R 7 , R 11 , and R 12 other than the group represented by formula (1B) are each independently is a hydrogen atom, In the general formula (1B), n1 is 0 or 1; L when n1 is 1 １ teeth, an unsubstituted arylene group having 6 to 13 ring carbon atoms, However, the unsubstituted arylene group having 6 to 13 ring carbon atoms is not a fused ring, Ar １ teeth, a heterocyclic group having four or more condensed substituted or unsubstituted rings, * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), However, R in the general formula (1A) １ At least one of R1 to R12 is a deuterium atom.

2. In the compound according to claim 1, n1 is 0. compound.

3. In the compound according to claim 1 , R １１ is a group represented by general formula (1B) compound.

4. In the compound according to claim 3, R １ ~R １０ and R １２ are all deuterium atoms, compound.

5. In the compound according to claim 1 , Ar １ is a group represented by the following general formula (1B-1), (1B-2), or (1B-3): compound. 【Chemistry 2】 (In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), n1 is 0 or 1; L when n1 is 1 １ teeth, an unsubstituted arylene group having 6 to 13 ring carbon atoms, However, the unsubstituted arylene group having 6 to 13 ring carbon atoms is not a fused ring. In the general formula (1B-1), R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ are each independently Hydrogen atom, 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 ) a group represented by -O-(R ９０４ ) a group represented by -S-(R ９０５ ) a group represented by -N(R ９０６ ) (R ９０７ ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), In the general formula (1B-2), R ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ each independently represents R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ is synonymous with * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), In the general formula (1B-3), R ５１ ~R ５５ , and R ８１ ~R ８４ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５１ ~R ５５ , and R ８１ ~R ８４ each independently represents R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ is synonymous with * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , and R ９０７ are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other, R ９０５ When there are multiple R ９０５ are the same or different from each other, R ９０６ When there are multiple R ９０６ are the same or different from each other, R ９０７ When there are multiple R ９０７ are the same or different from each other.)

6. In the compound according to claim 1 , The groups described as "substituted or unsubstituted" are all "unsubstituted" groups. The rings described as "substituted or unsubstituted" are all "unsubstituted" rings. compound.

7. Contains a compound according to any one of claims 1 to 6. Organic electroluminescent element.

8. The organic electroluminescence device according to claim 7, An anode; A cathode; an organic layer disposed between the anode and the cathode; At least one of the organic layers contains the compound. Organic electroluminescent element.

9. The organic electroluminescence device according to claim 8, the organic layer has a light-emitting region; the light emitting region comprises at least one light emitting layer; The light-emitting layer contains the compound. Organic electroluminescent element.

10. An anode; A cathode; a light emitting region disposed between the anode and the cathode; the light-emitting region includes a first light-emitting layer and a second light-emitting layer; The first light-emitting layer contains a first compound represented by the following general formula (100A): the second light-emitting layer contains a second compound, Organic electroluminescent element. 【Chemistry 3】 (In the general formula (100A), R 106 , R 107 , R 111 , and R １１２ one of which is a group represented by general formula (100B) R 101 to R 105 , R 108 to R 110 , and R 106 , R 107 , R 111 , and R other than the group represented by formula (100B) １１２ are each independently is a hydrogen atom, In the general formula (100B), n101 is 0 or 1, L when n101 is 1 １０１ teeth, an unsubstituted arylene group having 6 to 13 ring carbon atoms, However, the unsubstituted arylene group having 6 to 13 ring carbon atoms is not a fused ring. Ar １０１ teeth, a heterocyclic group having three or more condensed substituted or unsubstituted rings, * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), However, R in the general formula (100A) １０１ At least one of R111 to R112 is a deuterium atom.

11. The organic electroluminescence device according to claim 10, The triplet energy T of the first compound １ (H1) and the triplet energy T of the second compound １ (H2) satisfies the relationship of the following formula (Formula 1), Organic electroluminescent element. T １ (H1)>T １ (H2)…(Number 1)

12. The organic electroluminescence device according to claim 10, Ar １０１ is a heterocyclic group having four or more condensed substituted or unsubstituted rings; Organic electroluminescent element.

13. In the organic electroluminescence device according to claim 10, n101 is 0. Organic electroluminescent element.

14. The organic electroluminescence device according to claim 10, R １１１ is a group represented by general formula (100B), Organic electroluminescent element.

15. The organic electroluminescence device according to claim 14, R １０１ ~R １１０ and R １１２ are all deuterium atoms, Organic electroluminescent element.

16. The organic electroluminescence device according to claim 10, Ar １０１ is a group represented by the following general formula (1B-1), (1B-2), or (1B-3): Organic electroluminescent element. 【Chemistry 4】 (In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), n1 is 0 or 1, L when n1 is 1 １ teeth, an unsubstituted arylene group having 6 to 13 ring carbon atoms, However, the unsubstituted arylene group having 6 to 13 ring carbon atoms is not a fused ring. In the general formula (1B-1), R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ are each independently Hydrogen atom, 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 ) a group represented by -O-(R ９０４ ) a group represented by -S-(R ９０５ ) a group represented by -N(R ９０６ ) (R ９０７ ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), In the general formula (1B-2), R ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ each independently represents R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ is synonymous with * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), In the general formula (1B-3), R ５１ ~R ５５ , and R ８１ ~R ８４ At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５１ ~R ５５ , and R ８１ ~R ８４ each independently represents R in the general formula (1B-1). ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ is synonymous with * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , and R ９０７ are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other, R ９０５ When there are multiple R ９０５ are the same or different from each other, R ９０６ When there are multiple R ９０６ are the same or different from each other, R ９０７ When there are multiple R ９０７ are the same or different from each other.)

17. The organic electroluminescence device according to claim 10, The groups described as "substituted or unsubstituted" are all "unsubstituted" groups. The rings described as "substituted or unsubstituted" are all "unsubstituted" rings. Organic electroluminescent element.

18. The organic electroluminescence device according to claim 10, the first light-emitting layer and the second light-emitting layer are in direct contact with each other; Organic electroluminescent element.

19. The organic electroluminescence device according to claim 10, the first light-emitting layer is disposed between the anode and the second light-emitting layer; Organic electroluminescent element.

20. The organic electroluminescence device according to claim 10, the first light-emitting layer contains a first light-emitting compound, and the second light-emitting layer contains a second light-emitting compound; the first luminescent compound and the second luminescent compound are each independently a compound that exhibits luminescence having a maximum peak wavelength of 500 nm or less; Organic electroluminescent element.

21. The organic electroluminescence device according to claim 10, A hole transport layer is provided between the anode and the light emitting region. Organic electroluminescent element.

22. The organic electroluminescence device according to claim 10, An electron transport layer is provided between the cathode and the light emitting region. Organic electroluminescent element.

23. An electronic device comprising the organic electroluminescence element according to any one of claims 10 to 22.

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