Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device

Abstract

A compound represented by general formula (1). In general formula (1), R1 to R11 are each independently a hydrogen atom or a substituent group, provided that at least one among R1 to R8 is a substituted or unsubstituted carbazolyl group and the members of a set consisting of two or more among R1 to R11 that are neighboring are not bonded to each other, and R12 and R13 are each independently a group represented by general formula (12D), a substituted or unsubstituted aryl group having 6-50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5-50 ring atoms, provided that at least one among R12 and R13 is a group represented by general formula (12D).

Description

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

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

[0002] When a voltage is applied to an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device"), 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%. Fluorescent organic EL devices that utilize light emission from singlet excitons are increasingly being applied to full-color displays such as mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. In order to improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Documents 1 to 3). Examples of the performance of organic EL devices include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0003] International Publication No. 2020 / 009363 International Publication No. 2021 / 020942 International Publication No. 2021 / 020931

[0004] In order to improve the performance of electronic devices such as displays, further improvements in the performance of organic EL elements are desired.

[0005] An object of the present invention is to provide a compound capable of improving the luminous efficiency of an organic electroluminescence device. Another object of the present invention is to provide a material for an organic electroluminescence device containing the compound, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device.

[0006] According to one aspect of the present invention, there is provided a compound represented by the following general formula (1):

[0007]

[0008] (In the general formula (1), R １ ~R １１ 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 group represented by -Si(Rx)(Ry)(Rz), 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, with the proviso that R １ ~R ８ At least one of R is a substituted or unsubstituted carbazolyl group; １ ~R １１ Any pair of two or more adjacent groups of R １２ and R １３ are each independently a group represented by the following general formula (12D), 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, with the proviso that R １２ and R １３ At least one of the groups is a group represented by the following general formula (12D):

[0009]

[0010] (In the general formula (12D), R ２１ ~R ２４ any one of R is a bonding position to a nitrogen atom in the general formula (1), and R is not a bonding position to a nitrogen atom in the general formula (1). ２１ ~R ２４ , and R ２５ ~R ２８ 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 group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, and X is an oxygen atom, a sulfur atom, or N(R ２９ ), or C(R３０ ) (R ３１ ) and R ３０ and R ３１ are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R ２９ R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring ３０ and R which does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. ３１ 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, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R １３８ a group represented by -COOR １３９ a halogen atom, a cyano group, a nitro group, -P(=O)(R １４０ ) (R １４１ a group represented by —Ge(R １４２ ) (R １４３ ) (R １４４ ), a group represented by —B(R １４５ ) (R １４６ ) 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.) (Rx, Ry, and Rz in the general formula (1) and Rx, Ry, Rz, and R in the general formula (12D) are １３１ ~R１４６ 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, when there are multiple Rx's, the multiple Rx's are the same as or different from one another, when there are multiple Ry's, the multiple Ry's are the same as or different from one another, when there are multiple Rz's, the multiple Rz's are the same as or different from one another, R １３１ If there are multiple R １３１ are the same or different from each other, R １３２ If there are multiple R １３２ are the same or different from each other, R １３３ If there are multiple R １３３ are the same or different from each other, R １３４ If there are multiple R １３４ are the same or different from each other, R １３５ If there are multiple R １３５ are the same or different from each other, R １３６ If there are multiple R １３６ are the same or different from each other, R １３７ If there are multiple R １３７ are the same or different from each other, R １３８ If there are multiple R １３８ are the same or different from each other, R １３９ If there are multiple R １３９ are the same or different from each other, R １４０ If there are multiple R １４０ are the same or different from each other, R １４１ If there are multiple R １４１ are the same or different from each other, R １４２ If there are multiple R １４２ are the same or different from each other, R１４３ If there are multiple R １４３ are the same or different from each other, R １４４ If there are multiple R １４４ are the same or different from each other, R １４５ If there are multiple R １４５ are the same or different from each other, R １４６ If there are multiple R １４６ are the same or different from each other.)

[0011] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, which contains a compound according to one aspect of the present invention.

[0012] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising a cathode, an anode, and organic layers between the cathode and the anode, wherein at least one layer of the organic layers contains a compound according to one aspect of the present invention as compound M3.

[0013] 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.

[0014] According to one aspect of the present invention, a compound capable of improving the performance of an organic electroluminescence device can be provided. According to one aspect of the present invention, a material for an organic electroluminescence device containing the compound according to one aspect of the present invention, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device can be provided.

[0015] Fig. 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. Fig. 2 is a diagram showing a schematic diagram of an apparatus for measuring transient PL. Fig. 3 is a diagram showing an example of a decay curve of transient PL. Fig. 4 is a diagram showing the energy levels of a sensitizing material and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to a third embodiment of the present invention, as well as the relationship between energy transfer. Fig. 5 is a diagram showing the energy levels of a host material, a sensitizing material and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to a fourth embodiment of the present invention, as well as the relationship between energy transfer.

[0016] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0017] 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 marked with a symbol such as "R" or "D" representing a deuterium atom.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] 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.

[0023] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0024] 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.

[0025] "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.

[0026] 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).

[0027]

[0028]

[0029] 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.

[0030] "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.

[0031] 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).

[0032] 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).

[0033] 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.

[0034] 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.

[0035] 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).

[0036] 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):

[0037]

[0038]

[0039] 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:

[0040] 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.

[0041] 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].

[0042] 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].

[0043] 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):

[0044] 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).

[0045] "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.

[0046] 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.

[0047] 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.

[0048] "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.

[0049] 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.

[0050] 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.

[0051] - "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.

[0052] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group.

[0053] "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.

[0054] 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.

[0055] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0056] -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.

[0057] ・「-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.

[0058] ・"-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.

[0059] ・「-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.

[0060] "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.

[0061] "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.

[0062] "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.

[0063] - "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.

[0064] - "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.

[0065] - "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.

[0066] - "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.

[0067] - "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.

[0068] "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.

[0069] 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.

[0070] 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.

[0071] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0072]

[0073] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0074]

[0075] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0076] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0077]

[0078] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0079] 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.

[0080] "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.

[0081] "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.

[0082] "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.

[0083] 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).

[0084]

[0085]

[0086] 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.

[0087]

[0088] 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.

[0089]

[0090] 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.

[0091] 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).

[0092]

[0093]

[0094]

[0095] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0096]

[0097]

[0098]

[0099]

[0100] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0101] The above is the explanation of "substituents described in this specification."

[0102] "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.

[0103]

[0104] 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.

[0105] 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).

[0106]

[0107] 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.

[0108]

[0109] 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.

[0110] 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

[0111] 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.

[0112] 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").

[0113] 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.

[0114] 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.

[0115] 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.

[0116] 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."

[0117] 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.

[0118] 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.

[0119] In this specification, the expression "A≧B" means that the value of A is equal to the value of B, or the value of A is greater than the value of B. In this specification, the expression "A≦B" means that the value of A is equal to the value of B, or the value of A is smaller than the value of B.

[0120] [First Embodiment] The compound according to the first embodiment is a compound represented by the following general formula (1).

[0121]

[0122] (In the general formula (1), R １ ~R １１ 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 group represented by -Si(Rx)(Ry)(Rz), 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, with the proviso that R １ ~R ８ At least one of R is a substituted or unsubstituted carbazolyl group; １ ~R １１ Any pair of two or more adjacent groups of R １２and R １３ are each independently a group represented by the following general formula (12D), 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, with the proviso that R １２ and R １３ At least one of the groups is a group represented by the following general formula (12D):

[0123]

[0124] (In the general formula (12D), R ２１ ~R ２４ any one of R is a bonding position to a nitrogen atom in the general formula (1), and R is not a bonding position to a nitrogen atom in the general formula (1). ２１ ~R ２４ , and R ２５ ~R ２８ 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 group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, and X is an oxygen atom, a sulfur atom, or N(R ２９ ), or C(R ３０ ) (R ３１ ) and R ３０ and R ３１ are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and R ２９ R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring ３０ and R which does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. ３１are 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, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R １３８ a group represented by -COOR １３９ a halogen atom, a cyano group, a nitro group, -P(=O)(R １４０ ) (R １４１ a group represented by —Ge(R １４２ ) (R １４３ ) (R １４４ ), a group represented by —B(R １４５ ) (R １４６ ) 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.) (Rx, Ry, and Rz in the general formula (1) and Rx, Ry, Rz, and R in the general formula (12D) are １３１ ~R １４６ 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, when there are multiple Rx's, the multiple Rx's are the same as or different from one another, when there are multiple Ry's, the multiple Ry's are the same as or different from one another, when there are multiple Rz's, the multiple Rz's are the same as or different from one another, R１３１ If there are multiple R １３１ are the same or different from each other, R １３２ If there are multiple R １３２ are the same or different from each other, R １３３ If there are multiple R １３３ are the same or different from each other, R １３４ If there are multiple R １３４ are the same or different from each other, R １３５ If there are multiple R １３５ are the same or different from each other, R １３６ If there are multiple R １３６ are the same or different from each other, R １３７ If there are multiple R １３７ are the same or different from each other, R １３８ If there are multiple R １３８ are the same or different from each other, R １３９ If there are multiple R １３９ are the same or different from each other, R １４０ If there are multiple R １４０ are the same or different from each other, R １４１ If there are multiple R １４１ are the same or different from each other, R １４２ If there are multiple R １４２ are the same or different from each other, R １４３ If there are multiple R １４３ are the same or different from each other, R １４４ If there are multiple R １４４ are the same or different from each other, R １４５ If there are multiple R １４５ are the same or different from each other, R １４６ If there are multiple R １４６ are the same or different from each other.)

[0125] The compound according to this embodiment has a fused ring containing a boron atom and two nitrogen atoms as a mother skeleton, a carbazolyl group directly bonded to the mother skeleton, and a group represented by general formula (12D) directly bonded to at least one of the nitrogen atoms of the mother skeleton. The compound according to this embodiment having such a structure increases the oscillator strength of the compound and improves its luminescence properties. Furthermore, by using the compound according to this embodiment in the organic layer of an organic EL device, the luminous efficiency can be improved.

[0126] In addition, "R １ ~R １１ "Any pair of two or more adjacent groups among R １ ~R １１ This means that a pair of two or more adjacent rings among the above "does not form" either a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.

[0127] In the compound according to this embodiment, R １ ~R ８ At least one of R is a substituted or unsubstituted carbazolyl group, and R other than the carbazolyl group １ ~R ８ , and R ９ ~R １１ are preferably 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0128] In the compound according to this embodiment, R １ ~R ８ At least one of R is a substituted or unsubstituted carbazolyl group, and R other than the carbazolyl group １ ~R ８ , and R ９ ~R １１ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0129] In the compound according to this embodiment, R １ ~R ８ Among these, it is preferred that two of them are substituted or unsubstituted carbazolyl groups.

[0130] In the compound according to this embodiment, R １ ~R ４ one of which is a substituted or unsubstituted carbazolyl group, and R ５ ~R ８ Among these, it is preferred that one of them is a substituted or unsubstituted carbazolyl group.

[0131] In the compound according to this embodiment, R １ ~R ８ The substituted or unsubstituted carbazolyl group in the formula (I) is preferably a substituted or unsubstituted N-carbazolyl group.

[0132] In the compound according to this embodiment, R ２ and R ７ is preferably a substituted or unsubstituted carbazolyl group.

[0133] In the compound according to this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (11A).

[0134]

[0135] (In the general formula (11A), R １ , R ３ ~R ６ , and R ８ ~R １３ are R in the general formula (1), respectively. １ , R ３ ~R ６ , and R ８ ~R １３ is synonymous with R ４１ , R ４２ , R ４３ , and R ４４one 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, ４５ , R ４６ , R ４７ , and R ４８ 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, ４９ , R ５０ , R ５１ , and R ５２ 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, ５３ , R ５４ , R ５５ , and R ５６ 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 ４１ ~R ５６ 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, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R １３８ a group represented by -COOR １３９ a halogen atom, a cyano group, a nitro group, -P(=O)(R １４０ ) (R １４１ a group represented by —Ge(R １４２ ) (R １４３ ) (R １４４ ), a group represented by —B(R １４５ ) (R １４６ 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, １３１ ~R １４６ are R in the general formula (12D), respectively. １３１ ~R １４６ is synonymous with

[0136] In the compound according to this embodiment, R ２ and R ６ is also preferably a substituted or unsubstituted carbazolyl group.

[0137] In the compound according to this embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (11B).

[0138]

[0139] (In the general formula (11B), R １ , R ３ ~R ５ , and R ７ ~R １３ are R in the general formula (1), respectively. １ , R ３ ~R ５ , and R ７ ~R １３ is synonymous with R ４９ , R ５０ , R ５１ , and R ５２one 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, ５３ , R ５４ , R ５５ , and R ５６ 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, ５７ , R ５８ , R ５９ , and R ６０ 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, ６１ , R ６２ , R ６３ , and R ６４ 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 ４９ ~R ６４ 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, -N(R １３１ ) (R １３２ a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R １３８ a group represented by -COOR １３９ a halogen atom, a cyano group, a nitro group, -P(=O)(R １４０ ) (R １４１ a group represented by —Ge(R １４２ ) (R １４３ ) (R １４４ ), a group represented by —B(R １４５ ) (R １４６ 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, １３１ ~R １４６ are R in the general formula (12D), respectively. １３１ ~R １４６ is synonymous with

[0140] In the compound according to this embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (11C) or (11D).

[0141]

[0142] (R in the general formula (11C) １ , and R ３ ~R １３ are R in the general formula (1), respectively. １ , and R ３ ~R １３ and R in the general formula (11D) has the same meaning as １ ~R ６ and R ８ ~R １３ are R in the general formula (1), respectively. １ ~R ６ and R ８ ~R １３ and R in the general formula (11C) ６ and R ７ is not a substituted or unsubstituted carbazolyl group, but is R ２is not a substituted or unsubstituted carbazolyl group, and R ４１ , R ４２ , R ４３ , and R ４４ at least one pair of adjacent two or more of R in the general formula (11D) are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ４５ , R ４６ , R ４７ , and R ４８ at least one pair of adjacent two or more of R in the general formula (11C) 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, or are not bonded to each other, ４９ , R ５０ , R ５１ , and R ５２ at least one pair of adjacent two or more of R in the general formula (11C) 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, or are not bonded to each other, ５３ , R ５４ , R ５５ , and R ５６ 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 ４１ ~R ５６ 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, -N(R １３１ ) (R １３２a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ a group represented by —O—(R １３６ ), a group represented by —S—(R １３７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R １３８ a group represented by -COOR １３９ a halogen atom, a cyano group, a nitro group, -P(=O)(R １４０ ) (R １４１ a group represented by —Ge(R １４２ ) (R １４３ ) (R １４４ ), a group represented by —B(R １４５ ) (R １４６ 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, １３１ ~R １４６ are R in the general formula (12D), respectively. １３１ ~R １４６ is synonymous with

[0143] In the compound represented by the general formula (11C), R ５ ~R ７ In the compound represented by the general formula (11C), it is also preferable that at least one of R is 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. ６ or R ７ is also preferably 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.

[0144] In the compound represented by the general formula (11D), R ２ ~R４ In the compound represented by the general formula (11D), it is also preferable that at least one of R is 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. ２ or R ３ is also preferably 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.

[0145] In the compound according to this embodiment, R ２ It is also preferred that only R is a substituted or unsubstituted carbazolyl group. ７ It is also preferred that only the group is a substituted or unsubstituted carbazolyl group.

[0146] In the compound according to this embodiment, R ２１ is the bonding position to the nitrogen atom in the general formula (1), R ２２ is preferably a hydrogen atom, and R ２４ is the bonding position to the nitrogen atom in the general formula (1), R ２３ is preferably a hydrogen atom.

[0147] In the compound according to this embodiment, R １２ and R １３ and (12D) are preferably groups represented by the general formula (12D).

[0148] In the compound according to this embodiment, R １２ is a group represented by the general formula (12D), and R １３ is also preferably 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. １２is 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 １３ is also preferably a group represented by the general formula (12D).

[0149] In the compound according to this embodiment, R １２ is a group represented by the general formula (12D), and R １３ is also preferably a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms. １２ is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and R １３ is also preferably a group represented by the general formula (12D).

[0150] In the compound according to this embodiment, X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

[0151] In the compound according to this embodiment, R １ , R ３ , R ４ , R ５ , R ６ , R ８ , R ９ , and R １１ is also preferably a hydrogen atom.

[0152] In the compound according to this embodiment, R １０ is preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0153] In the compound according to this embodiment, R ２１ is preferably a hydrogen atom or a bonding position to the nitrogen atom in the general formula (1).

[0154] In the compound according to this embodiment, R ２２ and R ２４are 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 bonding position to the nitrogen atom in general formula (1).

[0155] In the compound according to this embodiment, R ２３ is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0156] R in the general formula (12D) ２１ is the bonding position with the nitrogen atom in the general formula (1), the group represented by the general formula (12D) is represented by the following general formula (12D-1). ２２ is the bonding position with the nitrogen atom in the general formula (1), the group represented by the general formula (12D) is represented by the following general formula (12D-2). ２３ is the bonding position with the nitrogen atom in the general formula (1), the group represented by the general formula (12D) is represented by the following general formula (12D-4). ２４ is the bonding position with the nitrogen atom in general formula (1), the group represented by general formula (12D) is represented by the following general formula (12D-3): In the compound according to this embodiment, the group represented by general formula (12D) is preferably the following general formula (12D-1), (12D-2), or (12D-3).

[0157]

[0158]

[0159] (In the general formulas (12D-1), (12D-2), (12D-3), and (12D-4), * indicates the bonding position with the nitrogen atom in the general formula (1), and R ２１ ~R ２８ are R in the general formula (12D), respectively. ２１ ~R ２８ is synonymous with

[0160] In the compound according to this embodiment, R in the general formula (12D-1) ２２ is preferably a hydrogen atom, and R in the general formula (12D-2) ２１ and R ２３ is preferably a hydrogen atom, and R in the general formula (12D-3) ２３ is preferably a hydrogen atom.

[0161] In the compound according to this embodiment, R １２ and R １３ is a group represented by the general formula (12D-1) above, the compound represented by the general formula (1) above is represented by the following general formula (110A). １２ and R １３ is a group represented by the general formula (12D-2), the compound represented by the general formula (1) is represented by the following general formula (110B). １２ and R １３ is a group represented by the general formula (12D-3), the compound represented by the general formula (1) is represented by the following general formula (110C).

[0162]

[0163]

[0164]

[0165] (In the general formulae (110A), (110B), and (110C), R １ ~R １１ are R in the general formula (1), respectively. １ ~R １１ and X and R ２１ ~R ２８ respectively represent X and R in the general formula (12D). ２１ ~R ２８ is synonymous with

[0166] In the compound according to this embodiment, R ２５ , R ２６ , R ２７ , and R ２８is preferably a hydrogen atom.

[0167] In the compound according to this embodiment, it is also preferable that the compound represented by the general formula (1) contains one or more deuterium atoms.

[0168] In the compound according to this embodiment, R １ ~R ８ , R １０ , and R １２ ~R １３ It is also preferred that one or more of the following contain one or more deuterium atoms.

[0169] In the compound according to this embodiment, R １ ~R ８ and R １０ It is also preferred that one or more of the following is a deuterium atom or a substituent containing one or more deuterium atoms.

[0170] In the compound according to this embodiment, R １２ and R １３ It is also preferred that one or more of the following contain one or more deuterium atoms.

[0171] In the compound according to this embodiment, it is also preferable that the group represented by the general formula (12D) contains one or more deuterium atoms. ２１ ~R ２８ It is also preferred that one or more of the following is a deuterium atom.

[0172] In the compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 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 an unsubstituted aralkyl group having 7 to 50 carbon atoms; —C(═O)R ９０８a group represented by -COOR ９０９ a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a group represented by —S(═O) ２ R ９３８ a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, ９０１ ~R ９０９ , and R ９３１ ~R ９３８ are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0173] In this specification, —O—(R ９０４ ) is a group represented by R ９０４ is a hydrogen atom, it is a hydroxy group. ９０５ ) is a group represented by R ９０５ is a hydrogen atom, it is a thiol group. ９３１ ) (R ９３２ ) is a group represented by R ９３１ and R ９３２ When —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ) is a group represented by R ９３３ , R ９３４ and R ９３５ is a substituent, it is a substituted germanium group. ９３６ ) (R ９３７ ) is a group represented by R ９３６ and R ９３７ is a substituent, it is a substituted boryl group.

[0174] In the compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0175] In the compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 ring atoms.

[0176] In the compounds according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0177] (Method for Producing Compound According to This Embodiment) The compound according to this embodiment can be produced according to the synthesis method described in the Examples below, or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target compound.

[0178] (Specific Examples of Compounds According to the Present Embodiment) Specific examples of compounds according to the present 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. In this specification, a methyl group may be represented as Me, and a phenyl group may be represented as Ph.

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[0367] Second Embodiment <Material for Organic Electroluminescence Device> The material for organic electroluminescence devices according to this embodiment contains the compound according to the first embodiment. One embodiment includes a material for organic electroluminescence devices containing only the compound according to the first embodiment. Another embodiment includes a material for organic electroluminescence devices containing the compound according to the first embodiment and another compound different from the compound according to the first embodiment. In the material for organic electroluminescence devices according to this embodiment, the compound according to the first embodiment is preferably a dopant material. In this case, the material for organic electroluminescence devices may contain the compound according to the first embodiment (preferably a fluorescent compound) as a dopant material and other compounds such as a host material and a sensitizing material.

[0368] [Third Embodiment] <Organic Electroluminescence Element> An organic EL element according to the third embodiment will be described. The organic EL element according to the third embodiment has a cathode, an anode, and an organic layer between the cathode and the anode. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic compound. At least one layer of the organic layer contains the compound according to the first embodiment as compound M3. Compound M3 may be referred to as the third compound.

[0369] (Organic Layer) In the organic EL element of the third embodiment, it is preferable that the organic layer includes an emitting layer, and the emitting layer contains compound M3 (third compound). In the organic EL element of the third embodiment, the organic layer may be composed of, for example, a single emitting layer, or may include a layer that can be used in an organic EL element. The layer that can be used in an organic EL element is not particularly limited, and examples thereof include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0370] The organic EL device according to the third embodiment includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode, the emitting layer containing a sensitizing material and a compound M3. The sensitizing material and the compound M3 are different compounds.

[0371] In the organic EL element of the third embodiment, a hole transport layer may be disposed between the anode and the light-emitting layer.

[0372] In the organic EL element of the third embodiment, an electron transport layer may be disposed between the cathode and the light-emitting layer.

[0373] Fig. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is configured by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, an emitting layer 5, an electron transport layer 8, and an electron injection layer 9. The present invention is not limited to the configuration of the organic EL element shown in Fig. 1.

[0374] (Light-emitting layer) In one embodiment, the sensitizing material and compound M3 are contained in a single layer. For example, when the organic EL device has one light-emitting layer, the sensitizing material and compound M3 are contained in the single light-emitting layer. When the organic EL device has multiple light-emitting layers, the sensitizing material and compound M3 are contained in any one of the multiple light-emitting layers. In one embodiment, compound M3 (third compound) is contained in the light-emitting layer as a fluorescent material.

[0375] In one embodiment, the light-emitting layer contains a sensitizing material and a compound M3 as a fluorescent material. In this embodiment, the sensitizing material is preferably one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescent compounds, and more preferably a delayed fluorescent compound. In this embodiment, when the light-emitting layer contains a delayed fluorescent compound as a sensitizing material, it is preferable that the light-emitting layer does not contain a phosphorescent metal complex.

[0376] In the light-emitting layer, recombination of holes and electrons is more likely to occur on the molecules of the sensitizing material rather than on the fluorescent material, and when the sensitizing material is a delayed fluorescent compound, it is thought that reverse intersystem crossing occurs from the lowest excited triplet state to the lowest excited singlet state. Thus, after the energy state transition to the lowest excited singlet state occurs in the sensitizing material, energy transfer occurs from the sensitizing material to the fluorescent material, and fluorescent emission from the lowest excited singlet state of the fluorescent material occurs. In this embodiment, if the sensitizing material is a delayed fluorescent compound that efficiently undergoes reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, energy loss is small, and the fluorescent material that receives the energy is thought to emit light with high efficiency.

[0377] [Fluorescent Material (Third Compound)] In this embodiment, the fluorescent material is not a phosphorescent metal complex. In this embodiment, the fluorescent material is preferably not a metal complex.

[0378] (Maximum Peak Wavelength) In the third embodiment, the maximum peak wavelength of the third compound (compound M3) as a fluorescent material is preferably 480 nm or less, more preferably 475 nm or less. In the third embodiment, the maximum peak wavelength of the third compound (compound M3) as a fluorescent material is preferably 430 nm or more, more preferably 440 nm or more. In this specification, the maximum peak wavelength of fluorescent emission may be referred to as the maximum peak wavelength of fluorescent emission. In the organic EL element of the third embodiment, the third compound (compound M3) preferably exhibits blue emission. In this specification, blue emission refers to emission having a maximum peak wavelength of the fluorescent spectrum in the range of 430 nm or more and 480 nm or less.

[0379] (FWHM of Emission Spectrum) In the third embodiment, the FWHM of the emission spectrum of the third compound (compound M3) serving as the fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less. FWHM is an abbreviation for full width at half maximum.

[0380] In this specification, the method for measuring the maximum peak wavelength of a compound is as follows. －６ mol / L or more, 10 －５ A toluene solution containing the compound dissolved at a concentration of 1000 mol / L or less is prepared and placed in a quartz cell. The emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample (toluene solution) is measured at room temperature (300 K) using a spectrofluorometer. The emission spectrum can be 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 is maximum is defined as the maximum peak wavelength. Note that in this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum fluorescence peak wavelength (FL-peak). The emission spectrum half width FWHM is the full width at half maximum at the maximum peak of the emission spectrum.

[0381] (Stokes Shift) In this embodiment, the Stokes shift of the third compound (compound M3) as the fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less. In this embodiment, the Stokes shift of the third compound (compound M3) as the fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. When the Stokes shift of the third compound (compound M3) is 20 nm or less, excitation energy can be reduced. When the Stokes shift of the third compound (compound M3) is 10 nm or more, self-absorption can be suppressed, and loss of efficiency can be reduced.

[0382] The Stokes shift can be measured by the following method. －５ The compound to be measured is dissolved in toluene at a concentration of 1000 mol / L to prepare a measurement sample. The measurement sample is placed in a quartz cell and irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the absorption spectrum, for example, a spectrophotometer U-3900 / 3900H model manufactured by Hitachi High-Tech Science Corporation. The compound to be measured is dissolved in 4.9 x 10 －６ The sample is dissolved in toluene at a concentration of 100 mol / L to prepare a measurement sample. The measurement sample placed in a quartz cell is irradiated with excitation light at room temperature (300 K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) is measured. A spectrophotometer can be used to measure the fluorescence spectrum, and for example, a Hitachi High-Tech Science F-7000 fluorescence spectrophotometer can be used. From these absorption and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength is calculated to determine the Stokes shift (SS). The unit of the Stokes shift SS is nm.

[0383] [Sensitizing Material] In this specification, the compound used as the sensitizing material may be referred to as a second compound or compound M2.

[0384] (Delayed Fluorescent Compound) In this embodiment, the delayed fluorescent compound is not a phosphorescent metal complex. In this embodiment, it is preferable that the delayed fluorescent compound is not a metal complex.

[0385] (Compound Represented by General Formula (H1)) In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H1).

[0386]

[0387] (In the general formula (H1), A Ｈ is a group having at least one partial structure selected from the group consisting of the following general formulae (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7), and (a-8), and D Ｈ is a group represented by the following general formula (221), (222) or (223), Ｈ represents a single bond, a substituted or unsubstituted aryl ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms, m is 1, 2, 3, 4, or 5, and a plurality of A Ｈ are the same or different from each other, n is 1, 2, 3, 4 or 5, and a plurality of D Ｈ are the same or different from each other.)

[0388]

[0389] (In the general formulae (a-1) to (a-8), * each independently represents a bonding position to another atom in the molecule of the delayed fluorescent compound.)

[0390]

[0391]

[0392]

[0393] (R in the general formula (221) ２１ ~R ２８at least one pair of adjacent two or more of R in the general formula (222) is 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 is not bonded to each other, ２２１ ~R ２２８ at least one pair of adjacent two or more of R in the general formula (223) is 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 is not bonded to each other, ２３１ ~R ２３８ 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 a substituted or unsubstituted monocycle in the general formula (221) and do not form a substituted or unsubstituted fused ring ２１ ~R ２８ R in the general formula (222) does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring. ２２１ ~R ２２８ and R in the general formula (223) which does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring. ２３１ ~R ２３８ 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 ９０７a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ 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, in the general formula (222) and the general formula (223), ring A, ring B, and ring C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formula (224) and general formula (225), ring A, ring B, and ring C are fused to an adjacent ring at any position, p, px, and py are each independently 1, 2, 3, or 4, when p is 2, 3, or 4, multiple rings A are the same or different from each other, when px is 2, 3, or 4, multiple rings B are the same or different from each other, when py is 2, 3, or 4, multiple rings C are the same or different from each other, * in the general formulas (221) to (223) represents L Ｈ indicates the bonding position with

[0394]

[0395] (In the general formula (224), r is 0, 2 or 4, and a plurality of R ２９ 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, or are not bonded to each other, and in the general formula (225), X Ａ is a sulfur atom, an oxygen atom, or C(R ２９１ ) (R ２９２ ) and R ２９１ and R ２９２are 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, or are not bonded to each other to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring ２９ , R ２９１ and R ２９２ 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 ９０８ a group represented by -COOR ９０９ a halogen atom, a cyano group, a nitro group, -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ 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, ２９ are the same or different from each other, and a plurality of R ２９１ are the same or different from each other, and a plurality of R ２９２ are the same or different from each other, and a plurality of X Ａ are the same or different from each other.)

[0396] (In the delayed fluorescent compound, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ９０８ , R ９０９ , R ９３１ , R ９３２ , R ９３３ , R ９３４ , R ９３５ , R ９３６ and R ９３７ 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 ９０８ If there are multiple R ９０８ are the same or different from each other, R ９０９ If there are multiple R ９０９ are the same or different from each other, R ９３１ If there are multiple R ９３１ are the same or different from each other, R９３２ If there are multiple R ９３２ are the same or different from each other, R ９３３ If there are multiple R ９３３ are the same or different from each other, R ９３４ If there are multiple R ９３４ are the same or different from each other, R ９３５ If there are multiple R ９３５ are the same or different from each other, R ９３６ If there are multiple R ９３６ are the same or different from each other, R ９３７ If there are multiple R ９３７ are the same or different from each other.)

[0397] In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H10).

[0398]

[0399] (In the general formula (H10), CN is a cyano group, and L Ｈ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, １１ and D １２ are each independently a group represented by the general formula (221), (222) or (223), m is 1, 2, 3, 4 or 5, nx is 0, 1, 2, 3, 4 or 5, ny is 0, 1, 2, 3, 4 or 5, nx + ny is 1, 2, 3, 4 or 5, D １１ and D １２ are the same or different from each other, and a plurality of D １１ are the same or different from each other, and a plurality of D １２ are the same or different from each other.)

[0400] In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H100).

[0401]

[0402] (In the general formula (H100), L Ｈ , D １１ , D １２ , m, nx, and ny are each L in the general formula (H10). Ｈ , D １１ , D １２ , m, nx and ny are synonymous with each other, and each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -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 ９０８ a group represented by -COOR ９０９ a cyano group, a nitro group, a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ 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 at least one R is a substituent, and at least one R as the substituent is L of the compound represented by general formula (H100). Ｈ is bonded to by a carbon-carbon bond, k is an integer of 1 or more, and the multiple R's are the same or different.

[0403] In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H101).

[0404]

[0405] (In the general formula (H101), D １１ and D １２ respectively represent D in the general formula (H10). １１ and D １２ each R is independently defined as R in the general formula (H100), m is 1, 2, 3, or 4, nx is 0, 1, 2, 3, or 4, ny is 0, 1, 2, 3, or 4, k is 1, 2, 3, or 4, nx+ny is 1, 2, 3, or 4, and m+nx+ny+k=6.

[0406] In this embodiment, the delayed fluorescent compound is preferably a compound represented by the following general formula (H110), (H120), or (H130).

[0407]

[0408] (In the general formulae (H110), (H120) and (H130), D １１ and D １２ respectively represent D in the general formula (H10). １１ and D １２ each R is independently defined as R in general formula (H100), nx is 0, 1, 2, or 3, ny is 0, 1, 2, or 3, k is 1, 2, or 3, nx+ny is 1, 2, or 3, and nx+ny+k=4.

[0409] In the present embodiment, the group represented by the general formula (222) in the delayed fluorescent compound is preferably any one group selected from the group consisting of groups represented by the following general formulae (22A), (22B), (22C), (22D), (22E), and (22F):

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416] (In the general formulae (22A), (22B), (22C), (22D), (22E) and (22F), R ２２１ ~R ２２８ are R in the general formula (222), respectively. ２２１ ~R ２２８ is synonymous with R ２２９ and R ２３０ are each independently R in the general formula (224). ２９ and X Ａ represents X in the general formula (225). Ａ In the general formulae (22A), (22B), (22C), (22D), (22E) and (22F), * indicates a bonding position.

[0417] In the organic EL element according to this embodiment, when the delayed fluorescent compound is a compound represented by general formula (H101), * in general formulas (22A), (22B), (22C), (22D), (22E), and (22F) is bonded to the benzene ring itself explicitly shown in general formula (H101).

[0418] In the delayed fluorescent compound of this embodiment, X in the general formulae (225), (22A), (22B), (22C), (22D), (22E), and (22F) Ａ is also preferably a sulfur atom or an oxygen atom.

[0419] In the delayed fluorescent compound of this embodiment, X in the general formulae (225), (22A), (22B), (22C), (22D), (22E), and (22F) Ａ But C(R ２９１ ) (R ２９２ ), then R ２９１ and R ２９２are each independently preferably 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, and more 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.

[0420] In the delayed fluorescent compound of this embodiment, R ２１ ~R ２８ In the delayed fluorescent compound of this embodiment, it is also preferable that any pair of adjacent two or more of R ２２１ ~R ２２８ In the delayed fluorescent compound of this embodiment, it is also preferable that any pair of adjacent two or more of R ２３１ ~R ２３８ It is also preferred that any pair of two or more adjacent groups of the above is not bonded to each other.

[0421] In the delayed fluorescence compound of the present embodiment, each R is preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0422] In the delayed fluorescence compound of the present embodiment, each R is preferably independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, 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.

[0423] R in the delayed fluorescent compound of this embodiment ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R ２９are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0424] R in the delayed fluorescent compound of this embodiment ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R ２９ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, 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.

[0425] In the delayed fluorescent compound of this embodiment, R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R ２９ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0426] In the delayed fluorescent compound of this embodiment, R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, 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, ２１ ~R ２８ , R ２２１ ~R ２２８ , R ２３１ ~R ２３８、 and R ２９are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, 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.

[0427] In the delayed fluorescence compound according to the present embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 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 an unsubstituted aralkyl group having 7 to 50 carbon atoms; —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９３１ ) (R ９３２ a group represented by —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ), a group represented by —B(R ９３６ ) (R ９３７ a group represented by —S(═O) ２ R ９３８ a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, ９０１ ~R ９０９ , and R ９３１ ~R ９３８ are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0428] In the delayed fluorescence compound according to this embodiment, the substituent in the case of "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0429] In the delayed fluorescence compound according to this embodiment, the substituent in the case of "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0430] In the delayed fluorescent compound according to this embodiment, it is also preferable that all of the groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0431] (Thermally activated delayed fluorescence) In this specification, thermally activated delayed fluorescence may be referred to as delayed fluorescence. Delayed fluorescence is explained on pages 261 to 268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chinaya, published by Kodansha). In this document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is １３ It has been explained that if the transition probability can be reduced, reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state occurs with high efficiency, resulting in the manifestation of thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document explains the mechanism of delayed fluorescence generation. The TADF mechanism utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet levels is used. Known examples of compounds exhibiting thermally activated delayed fluorescence (TADF properties) (hereinafter also referred to as TADF compounds) include compounds in which a donor moiety and an acceptor moiety are bonded within the molecule.

[0432] In general, delayed fluorescence can be confirmed by transient PL (Photoluminescence) measurement.

[0433] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a technique in which a sample is excited by irradiating it with a pulsed laser and then measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in TADF compounds is classified into emission components from singlet excitons generated during the initial PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emission from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between emission from singlet excitons generated during the initial PL excitation and emission from singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be determined.

[0434] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Figure 2. An example of a method for measuring transient PL and an analysis of the behavior of delayed fluorescence will be described below using Figure 2.

[0435] 2 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in FIG. 2.

[0436] The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, in which the doping material is doped at a concentration of 12 mass % relative to the matrix material.

[0437] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material. Emission light is extracted in a direction 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by a spectrometer 103, forming a two-dimensional image in a streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. Cutting out this two-dimensional image along a predetermined time axis yields an emission spectrum in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, cutting out the two-dimensional image along the wavelength axis yields a decay curve (transient PL) in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[0438] For example, a thin film sample A was prepared as described above using the following compound HX1 as the matrix material and the following compound DX1 as the doping material, and transient PL measurement was carried out.

[0439]

[0440] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following compound HX2 as a matrix material and the above-mentioned compound DX1 as a doping material.

[0441] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0442]

[0443] As described above, transient PL measurement can be used to obtain an emission decay curve with the vertical axis representing emission intensity and the horizontal axis representing time. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence, which decays slowly, to the intensity of the fluorescence, which decays quickly, is somewhat large.

[0444] Specifically, luminescence from delayed fluorescent materials includes prompt luminescence and delay luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength that the delayed fluorescent material absorbs. Delay luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0445] The amounts of Prompt luminescence and Delay luminescence and their ratio can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amounts of Prompt luminescence and Delay luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2.

[0446] Furthermore, to measure the delayed fluorescence of the delayed fluorescent compound according to this embodiment, a sample prepared by the following method is used. For example, the delayed fluorescent compound according to this embodiment is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. To prevent quenching by oxygen, the sample solution is frozen and degassed, and then sealed in a lidded cell under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield is calculated according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0447] In this embodiment, the amount of prompt luminescence (prompt luminescence) of the compound to be measured is X Ｐ The amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X ＰThe amount and ratio of prompt luminescence and delay luminescence of compounds other than the delayed fluorescent compound in this specification are measured in the same manner as the amount and ratio of prompt luminescence and delay luminescence of the delayed fluorescent compound according to this embodiment.

[0448] (ΔST) In this embodiment, the lowest excited singlet energy S １ and the energy gap T at 77[K] ７７Ｋ The difference between (S １ -T ７７Ｋ ) is defined as ΔST.

[0449] In this embodiment, the lowest excited singlet energy S of the delayed fluorescent compound １ (M2) and the energy gap T at 77 [K] of the delayed fluorescent compound ７７Ｋ The difference ΔST(M2) from (M2) is preferably less than 0.5 eV, more preferably less than 0.3 eV, even more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the relationship of the following formula (Mathematical Formula 2), (Mathematical Formula 2A), (Mathematical Formula 2B), (Mathematical Formula 2C), or (Mathematical Formula 2D). ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.5eV...(Math. 2) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV...(Math. 2A) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.2eV...(Math 2B) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.1eV...(Math. 2C) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.01eV...(Math 2D)

[0450] (Relationship Between Triplet Energy and Energy Gap at 77 K) Here, the relationship between triplet energy and the energy gap at 77 K will be described. In this embodiment, the energy gap at 77 K differs from the triplet energy as typically defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving a compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. A phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) is measured for this sample at low temperature (77 K). A tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated using a predetermined conversion formula based on the wavelength value at the intersection of the tangent line and the horizontal axis. Among the compounds according to this embodiment, the thermally activated delayed fluorescence compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 K), resulting in a mixture of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as above contains light emission from both the excited singlet state and the excited triplet state, and it is difficult to clearly distinguish which state the light emission is from, but the triplet energy value is considered to be basically dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that it is different in the strict sense, the value measured as follows is referred to as the energy gap T ７７Ｋ The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to obtain a solution with a concentration of 10 μmol / L, and this solution is placed in a quartz cell to be used as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. ｅｄｇｅ Based on the energy gap T at 77 [K], the amount of energy calculated from the following conversion formula (F1) is ７７Ｋ Conversion formula (F1): T ７７Ｋ [eV]=1239.85 / λｅｄｇｅ

[0451] 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.

[0452] (Lowest excited singlet energy S １ ) The lowest excited singlet energy S １ The following method can be used as a measurement method (sometimes referred to as the solution method): A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K). A tangent line is drawn to the trailing 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 calculate the lowest excited singlet energy. Conversion formula (F2): S １ [eV]=1239.85 / λedge. The absorption spectrum measuring device may be, for example, a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd., but is not limited to this.

[0453] 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.

[0454] (Method for producing delayed fluorescent compound) The delayed fluorescent compound can be produced by a known method. The delayed fluorescent compound can also be produced by following the known method and using known alternative reactions and raw materials suited to the target product.

[0455] (Specific Examples of Delayed Fluorescence Compound) Specific examples of the delayed fluorescence compound include the following compounds, however, the present invention is not limited to these specific examples.

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462] (Relationship between Sensitizing Material and Fluorescent Material in Emitting Layer) In one embodiment, the sensitizing material is the delayed fluorescent compound. In one embodiment, the emitting layer contains a delayed fluorescent compound as a sensitizing material, and may not contain a phosphorescent metal complex.

[0463] FIG. 4 is a diagram showing an example of the relationship between the energy levels of a sensitizing material and a fluorescent material when an emitting layer contains a delayed fluorescent compound (second compound (compound M2)) as a sensitizing material and a fluorescent material (third compound (compound M3)). In FIG. 4, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M2) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M2) to S1(M3) in FIG. 4 represents Förster energy transfer from the lowest excited singlet state of the delayed fluorescent compound to the lowest excited singlet state of the fluorescent material. As shown in Figure 4, when a compound with a small ΔST (M2) is used as the delayed fluorescent compound, the lowest excited triplet state T1 (M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1 (M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1 (M2) of the delayed fluorescent compound to the fluorescent material, generating the lowest excited singlet state S1 (M3). As a result, fluorescence emission from the lowest excited singlet state S1 (M3) of the fluorescent material can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0464] In the organic EL device according to the third embodiment, the minimum excited singlet energy S １ (M2) and the lowest excited singlet energy S of the fluorescent material １ It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical Formula 4): S １ (M2) > S １ (M3) ...(Math. 4)

[0465] In one embodiment, the energy gap T at 77 K of the sensitizing material ７７Ｋ (M2) and the energy gap T of the fluorescent material at 77 [K] ７７Ｋ It is also preferable that (M3) satisfies the relationship of the following formula (Formula 6A): T ７７Ｋ (M2) > T ７７Ｋ(M3) ...(Math 6A)

[0466] When the organic EL element of the third embodiment is caused to emit light, it is preferable that the fluorescent material in the light-emitting layer mainly emits light.

[0467] The maximum peak wavelength of light emitted from the organic EL element is measured as follows: ２ A 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).

[0468] (Compound Content in Light-Emitting Layer) The contents of the sensitizing material (compound M2) and the fluorescent material (compound M3) contained in the light-emitting layer are preferably within the following ranges, for example. The content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of compound M2 may be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99.9% by mass or less, or even 99% by mass or more and 99.9% by mass or less. The content of compound M3 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. Note that this embodiment does not exclude the case where the light-emitting layer contains materials other than compound M2 and compound M3. The light-emitting layer may contain only one type of compound M2, or may contain two or more types of compound M2. The light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3.

[0469] (Thickness of the Light-Emitting Layer) The thickness of the light-emitting layer in the organic EL element of this embodiment 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, and when the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress an increase in driving voltage.

[0470] The structure of the organic EL element will be further described.

[0471] (Substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include 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. Inorganic vapor deposition films can also be used.

[0472] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium 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), or nitrides of metal materials (e.g., titanium nitride).

[0473] 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.

[0474] Of the organic 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.

[0475] 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), alloys containing these (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and 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.

[0476] When the organic EL element is a bottom-emission type, the anode is preferably formed of a metal material having optical transparency or semi-transparency that transmits light from the light-emitting layer. In this specification, optical transparency or semi-transparency means a property that transmits 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The optically transparent or semi-transparent metal material can be appropriately selected from the materials listed in the anode section.

[0477] When the organic EL device is a top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a metal material having optical reflectivity. In this specification, optical reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having optical reflectivity can be appropriately selected from the materials listed in the anode section. The anode may be composed of only a reflective layer, or may have a multilayer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer be disposed between the reflective layer and the hole-transporting region. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0478] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0479] 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.

[0480] 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, and indium oxide-tin oxide containing silicon or silicon oxide. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0481] When the organic EL element is a bottom-emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed of a metal material having light reflectivity. The metal material having light reflectivity can be appropriately selected from the materials listed in the section on the cathode.

[0482] When the organic EL element is a top-emission type, the cathode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the cathode section.

[0483] The organic EL element according to this embodiment may be a bottom-emission organic EL element. The organic EL element according to this embodiment may also be a top-emission organic EL element. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflectivity. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflective electrode having light reflectivity, and the cathode is a light-transmitting electrode having light transparency.

[0484] (Capping Layer) When the organic EL element is a top-emission type, the organic EL element usually has a capping layer on the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. A laminate obtained by stacking layers containing these substances can also be used as the capping layer.

[0485] (Hole Injection Layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide. 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 Examples of the compound having high hole injection properties include aromatic amine compounds such as 1,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1). Furthermore, examples of the compound having high hole injection properties include polymer compounds (oligomers, dendrimers, polymers, etc.). 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, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0486] (Hole Transport Layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. 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, 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 hole-transporting layer may be a material having a hole mobility of 1 / Vs or more. Carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth may be used for the hole-transporting layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used. However, other materials may also be used as long as they have a higher hole-transporting property than electron-transporting property. The layer containing the material having a high hole-transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned materials are stacked.

[0487] (Electron Transport Layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 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, and 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: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. －６ cm ２ / Vs or more. Note that other substances may be used as the electron-transporting layer as long as they have a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be a single layer or a stack of two or more layers made of the above-mentioned substances. A polymer compound may also be used for the electron-transporting layer. 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 may be used.

[0488] (Electron Injection Layer) The electron injection layer is a layer containing a substance with high electron injection properties. Examples of the electron injection layer include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), and calcium fluoride (CaF ２Alkali metals, alkaline earth metals, or compounds thereof, such as lithium oxide (LiOx), may be used. Alternatively, a material having electron transport properties containing an alkali metal, alkaline earth metal, or compound thereof, such as magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material obtained by mixing an organic compound with an electron donor (donor) may be used for the electron injection layer. 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 in transporting the generated electrons. Specifically, the above-mentioned materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) may 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 preferred, including 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.

[0489] (Layer Formation Method) The method for forming each layer of the organic EL element according to the third 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.

[0490] (Film Thickness) The film thickness of each organic layer in the organic EL element according to the third 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.

[0491] In the organic EL element according to the third embodiment, the light-emitting layer contains the compound according to the first embodiment (compound M3 (third compound)), and therefore, according to the third embodiment, the luminous efficiency of the organic EL element can be improved. The organic EL element according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0492] [Fourth Embodiment] The configuration of an organic EL element according to a fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0493] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer further contains a host material. Other features are the same as those of the third embodiment. In this specification, the compound used as the host material may be referred to as a first compound or compound M1. That is, in the fourth embodiment, the light-emitting layer contains a host material (first compound (compound M1)), a sensitizing material (second compound (compound M2)), and a fluorescent material (third compound (compound M3)).

[0494] (Light-emitting layer) In one embodiment, the host material, the sensitizing material, and the fluorescent material are contained in a single layer. For example, when the organic EL device has one light-emitting layer, the host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer. When the organic EL device has multiple light-emitting layers, the host material, the sensitizing material, and the fluorescent material are contained in a single light-emitting layer among the multiple light-emitting layers.

[0495] In one embodiment, when the light-emitting layer contains a delayed fluorescent compound as a sensitizing material, the light-emitting layer does not contain a phosphorescent metal complex.

[0496] [Host Material] In the fourth embodiment, the host material is a first compound (compound M1) containing, in one molecule, one or more partial structures selected from the group consisting of partial structures represented by the following general formulas (101) to (118):

[0497]

[0498]

[0499] (In the general formula (101), A １１ ~A １６ are each independently a nitrogen atom, CR １１ or a carbon atom bonded to another atom or structure in the molecule of the first compound, １１ ~A １６ At least one of R is a carbon atom bonded to another atom or another structure in the molecule of the first compound, １１ If there are multiple R １１ are the same or different, and multiple R １１ one or more pairs of adjacent two or more of the following are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other; and in the general formula (102), １ ~A ４ are each independently a nitrogen atom, CR １２ or a carbon atom bonded to another atom or structure in the molecule of the first compound, R １２ are each independently a hydrogen atom or a substituent, or an adjacent R １２ any one or more pairs of R are bonded to each other to form a ring, １２ If there are multiple R １２ are the same or different, and multiple R １２one or more pairs of adjacent two or more of X 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, １０ is NR １３ , C(R １４ ) (R １５ ), Si(R １６ ) (R １７ ), an oxygen atom, a sulfur atom, a nitrogen atom bonded to another atom or another structure in the molecule of the first compound, R １８ and a carbon atom bonded to another atom or another structure in the molecule of the first compound, or R １９ and a silicon atom bonded to another atom or another structure in the molecule of the first compound, １ ~A ４ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in R is bonded to another atom or another structure in the molecule of the first compound, １４ and R １５ 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 １６ and R １７ are bonded to each other to form a substituted or unsubstituted monocycle, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and in the general formula (103), R １１５ and R １１６ 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, or are not bonded to each other, and in the general formulae (101) to (104), R １１ , R １２ , R １４ , R１５ , R １６ , R １７ , R １１５ and R １１６ , and R １３ , R １８ , R １９ and R １１７ 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 group represented by —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９１０ ) (R ９１１ ), a group represented by —P(═O)(OR ９１２ ) (OR ９１３ a group represented by —Ge(R ９１４ ) (R ９１５ ) (R ９１６ ), a group represented by —B(R ９１７ ) (R ９１８), a substituted or unsubstituted aralkyl group having 7 to 50 ring atoms, 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 formulae (103) to (118), * represents a bonding site to another atom or another structure in the molecule of the first compound, and when the first compound has a plurality of partial structures represented by the general formulae (101) to (104), the plurality of partial structures represented by the general formulae (101) are the same or different from each other, the plurality of partial structures represented by the general formulae (102) are the same or different from each other, the plurality of partial structures represented by the general formulae (103) are the same or different from each other, and the plurality of partial structures represented by the general formula (104) are the same or different from each other.

[0500] (In the first compound, R ９０１ ~R ９１８ 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 ９０７If there are multiple R ９０７ are the same or different from each other, R ９０８ If there are multiple R ９０８ are the same or different from each other, R ９０９ If there are multiple R ９０９ are the same or different from each other, R ９１０ If there are multiple R ９１０ are the same or different from each other, R ９１１ If there are multiple R ９１１ are the same or different from each other, R ９１２ If there are multiple R ９１２ are the same or different from each other, R ９１３ If there are multiple R ９１３ are the same or different from each other, R ９１４ If there are multiple R ９１４ are the same or different from each other, R ９１５ If there are multiple R ９１５ are the same or different from each other, R ９１６ If there are multiple R ９１６ are the same or different from each other, R ９１７ If there are multiple R ９１７ are the same or different from each other, R ９１８ If there are multiple R ９１８ are the same or different from each other.)

[0501] In the general formula (102), X １０ is "a nitrogen atom bonded to another atom or another structure in the molecule of the first compound", the general formula (102) is represented by the following general formula (102-1): １０ "R １８ and a carbon atom bonded to another atom or another structure in the molecule of the first compound, the general formula (102) is represented by the following general formula (102-2): １０ "R１９ and a silicon atom bonded to another atom or another structure in the molecule of the first compound, the general formula (102) is represented by the following general formula (102-3). １ ~A ４ are each independently A in the general formula (102). １ ~A ４ is synonymous with R １８ and R １９ are each independently R in the general formula (102). １２ and * is the point of attachment to another atom or other structure in the molecule of the first compound.

[0502]

[0503] In one embodiment, the host material has at least one partial structure represented by the general formula (101). In one embodiment, the partial structure represented by the general formula (101) is at least one selected from the group consisting of partial structures represented by the following general formulas (A11) to (A19):

[0504]

[0505]

[0506] (In the general formulae (A11) to (A16), A １２ ~A １６ are each independently a nitrogen atom or CR １１ and R １１ is R in the general formula (101). １１ and * represents a bonding site to another atom or another structure in the molecule of the first compound. In the general formulae (A17) and (A18), A １１ ~A ２２ are each independently a nitrogen atom or CR １１ or a carbon atom bonded to another atom or structure in the molecule of the first compound, R １１ are each independently R in the general formula (101). １１ is synonymous with A １１ ~A２２ at least one of A is a carbon atom bonded to another atom or another structure in the molecule of the first compound, １１ ~A １８ are each independently a nitrogen atom or CR １１ or a carbon atom bonded to another atom or structure in the molecule of the first compound, R １１ are each independently R in the general formula (101). １１ is synonymous with X １１ and X １２ each independently represents X in the general formula (102). １０ and A １１ ~A １８ Carbon atoms in X １１ and X １２ Nitrogen atom in X １１ and X １２ Carbon atoms in １１ and X １２ At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the first compound.

[0507] In one embodiment, the host material has at least one partial structure represented by the general formula (102). In one embodiment, the partial structure represented by the general formula (102) is at least one selected from the group consisting of partial structures represented by the following general formulas (B11) to (B24):

[0508]

[0509] (In the general formulae (B11) to (B16), Ax １ ~Ax ４ are each independently a nitrogen atom or CR １２ and R １２ are each independently R in the general formula (102). １２ is synonymous with X １０ represents X in the general formula (102). １０* represents a bonding site to another atom or another structure in the molecule of the first compound, and in general formula (B17), Ax １ , Ax ２ and Ay １ ~Ay ４ are each independently a nitrogen atom or CR １２ or a carbon atom bonded to another atom or structure in the molecule of the first compound, R １２ are each independently R in the general formula (102). １２ is synonymous with X １０ represents X in the general formula (102). １０ where Ax １ , Ax ２ and Ay １ ~Ay ４ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ at least one of the silicon atoms in the general formula (B18) is bonded to another atom or another structure in the molecule of the first compound, １ ~Ay ８ are each independently a nitrogen atom or CR １２ or a carbon atom bonded to another atom or structure in the molecule of the first compound, R １２ are each independently R in the general formula (102). １２ is synonymous with X １０ represents X in the general formula (102). １０ and Ay １ ~Ay ８ Carbon atoms in X １０ Nitrogen atom in X １０ Carbon atoms and X in １０ At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the first compound.

[0510]

[0511] (In the general formulae (B19) to (B24), Ay１ ~Ay ８ and Ay ９ ~Ay １２ are each independently a nitrogen atom or CR １２ or a carbon atom bonded to another atom or structure in the molecule of the first compound, R １２ are each independently R in the general formula (102). １２ is synonymous with X ９ and X １０ each independently represents X in the general formula (102). １０ Ay is synonymous with １ ~Ay ８ and Ay ９ ~Ay １２ Carbon atoms in X ９ and X １０ Nitrogen atom in X ９ and X １０ Carbon atoms in ９ and X １０ At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the first compound.

[0512] In the first compound of the fourth embodiment, R １１、 R １２ and R １１５ ~R １１７ are each independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 30 carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, a thiol group, an unsubstituted alkylthio group having 1 to 30 carbon atoms, or an unsubstituted arylthio group having 6 to 30 ring carbon atoms. １１、 R １２and R １１５ ~R １１７ are each independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, a thiol group, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms. １１、 R １２ and R １１５ ~R １１７ is more preferably a hydrogen atom.

[0513] In the first compound of the fourth embodiment, X １０ R in １３ ~R １９ , and X ９ R in １３ ~R １９ (X １０ R in １３ ~R １９ and the same meaning as above) are preferably each independently a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms. １０ R in １３ ~R １９ , and X ９ R in １３ ~R １９are each independently a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms. １０ R in １３ ~R １９ , and X ９ R in １３ ~R １９ and are each independently an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0514] Examples of the partial structure represented by any one of the general formulae (101) to (118) include partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125). It is also preferable that the first compound contains at least one of the partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125) in one molecule.

[0515]

[0516] In the general formulae (A101) to (A107), R １０１ ~R １０６ are each independently R in the general formula (101). １１ is synonymous with R １０１ ~R １０６ At least one of the R １０１ and R １０２ Group R １０２ and R １０３ Group R １０３ and R １０４ Group R １０４ and R １０５ Group R １０５ and R １０６ and R １０６ and R １０１one or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other.

[0517]

[0518] In the general formulae (A108) and (A109), R １１０ are each independently R in the general formula (101). １１ is synonymous with R １１０ At least one of R is a single bond bonding to another atom or another structure in the molecule of the first compound, １１０ are the same or different, and multiple R １１０ one or more pairs of adjacent two or more of these are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0519]

[0520] In the general formulae (A110) to (A114), R １１０ and R １１２ ~R １１４ are each independently R in the general formula (101). １１ is synonymous with X １１０ each independently represents X in the general formula (102). １０ where R １１０ and R １１２ ~R １１４ At least one of X is a single bond bonding to another atom or another structure in the molecule of the first compound, or １１０ At least one of the nitrogen atom, carbon atom, and silicon atom in the formula (I) is bonded to another atom or another structure in the molecule of the first compound, and a plurality of R １１０ In the general formulae (A110) to (A114), a plurality of R １１０ a set of two or more adjacent １１２ and R １１３ and X １１０ R in１４ and R １５ The set (X １０ R in １４ and R １５ (same as the set of X) １１０ R in １６ and R １７ The set (X １０ R in １６ and R １７ one or more pairs of (same meaning as a pair of) are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0521]

[0522] In the general formulae (A115) to (A119), R １１０ and R １１２ ~R １１４ are each independently R in the general formula (101). １１ where R １１０ and R １１２ ~R １１４ At least one of R is a single bond bonding to another atom or another structure in the molecule of the first compound, １１０ In the general formulae (A115) to (A119), a plurality of R １１０ and R １１２ and R １１３ One or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, a substituted or unsubstituted fused ring, or are not bonded to each other.

[0523]

[0524] In the general formulae (A120) and (A121), R １１０ are each independently R in the general formula (101). １１ where R １１０ At least one of R is a single bond bonding to another atom or another structure in the molecule of the first compound, １１０In the general formulae (A120) to (A121), a plurality of R １１０ one or more pairs of adjacent two or more of these are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0525]

[0526] In the general formulae (B101) to (B109), R １１４ and R １２１ ~R １３１ are each independently R in the general formula (102). １２ where R １１４ and R １２１ ~R １３１ At least one of R is a single bond bonding to another atom or another structure in the molecule of the first compound. １２２ and R １２３ Group R １２３ and R １１４ and R １１４ and R １２１ In the general formulae (B105) and (B106), one or more of the pairs of R are bonded to each other to form a substituted or unsubstituted monocycle, or to form a substituted or unsubstituted fused ring, or are not bonded to each other. １２４ and R １２５ Group R １２５ and R １２６ Group R １２６ and R １２７ Group R １２７ and R １２８ and R １２８ and R １２９ In the general formula (B107), one or more of the pairs of R are bonded to each other to form a substituted or unsubstituted monocycle, or to form a substituted or unsubstituted fused ring, or are not bonded to each other. １２４ and R １２５ Group R １２５ and R １２６ Group R １２６ and R１２７ Group R １２７ and R １２８ Group R １２８ and R １２９ Group R １２９ and R １１４ and R １１４ and R １２４ In the general formulae (B108) and (B109), one or more of the pairs of R are bonded to each other to form a substituted or unsubstituted monocycle, or to form a substituted or unsubstituted fused ring, or are not bonded to each other. １２４ and R １２５ Group R １２５ and R １２６ Group R １３０ and R １３１ and R １３１ and R １２９ one or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other.

[0527]

[0528] In the general formulae (B110) to (B117), R １１０ and R １３２ ~R １３５ are each independently R in the general formula (102). １２ where R １１０ and R １３２ ~R １３５ At least one of R is a single bond bonding to another atom or another structure in the molecule of the first compound, １１０ In the general formulae (B110) to (B117), a plurality of R １１０ and R １３２ and R １３３ one or more of the pairs of may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other.

[0529]

[0530] In the general formulae (B118) to (B123), R １１０ are each independently R in the general formula (102). １２ Xa and Xb each independently represent X in the general formula (102). １０ where R １１０ At least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa and Xb are single bonds bonding to other atoms or other structures in the molecule of the first compound, or at least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa and Xb are single bonds bonding to other atoms or other structures in the molecule of the first compound, and a plurality of R １１０ In the general formulae (B118) to (B123), a plurality of R １１０ a pair of adjacent two or more of R in Xa １４ and R １５ and R in Xb １４ and R １５ The set (X １０ R in １４ and R １５ (same meaning as the set of Xa) and R １６ and R １７ and R in Xb １６ and R １７ The set (X １０ R in １６ and R １７ one or more pairs of (same meaning as a pair of) are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0531]

[0532] In the general formulae (B124) and (B125), R １１０ are each independently R in the general formula (102). １２ Xa, Xb, and Xc each independently represent X in the general formula (102). １０ where R １１０At least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa, Xb, and Xc are single bonds bonding to other atoms or other structures in the molecule of the first compound, or at least one of the nitrogen atoms, carbon atoms, and silicon atoms in Xa, Xb, and Xc are single bonds bonding to other atoms or other structures in the molecule of the first compound, and a plurality of R １１０ In the general formulae (B124) and (B125), a plurality of R １１０ and R in Xa, Xb, and Xc. １４ and R １５ The set (X １０ R in １４ and R １５ (same meaning as a set of Xa, Xb and Xc) and R １６ and R １７ The set (X １０ Oke R １６ and R １７ one or more pairs of (same meaning as a pair of) are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0533] In the general formulae (A101) to (A121) and (B101) to (B125), R １１０ , R １０１ ~R １０６ , R １１２ ~R １１４ , R １２１ ~R １３１ and R １３２ ~R １３５ are each independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms; and even more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0534] In the general formulae (A101) to (A121) and (B101) to (B125), Xa, Xb, Xc and X １１０ R in １３ ~R １９ (X １０ R in １３ ~R １９ and the like) are each independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms; and even more preferably an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0535] In the fourth embodiment, the first compound preferably has at least one of (I) a cyano group, an amino group, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, or (II) a monovalent or higher residue derived from any of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted indole, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted phenanthrene, and substituted or unsubstituted triphenylene.

[0536] In the fourth embodiment, it is more preferable that the first compound has (III) at least one cyano group, or (IV) at least one monovalent or higher residue derived from any of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.

[0537] In the fourth embodiment, it is more preferable that the first compound has at least one monovalent or higher residue derived from any one of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, and substituted or unsubstituted pyrimidine.

[0538] In the fourth embodiment, the first compound preferably has at least one monovalent or higher valent residue derived from a substituted or unsubstituted carbazole.

[0539] In the fourth embodiment, the first compound preferably has at least one partial structure represented by the following general formula (15).

[0540]

[0541] (In the general formula (15), R １５０ ~R １５８ At least one of R is a single bond bonding to another atom or another structure in the molecule of the first compound, and R is not a single bond. １５０ ~R １５８ 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 group represented by —C(═O)R ９０８ a group represented by -COOR ９０９ a group represented by -P(=O)(R ９１０ ) (R ９１１ a group represented by —Ge(R ９１２ ) (R ９１３ ) (R ９１４ ), a group represented by —B(R ９１５ ) (R ９１６ ) a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, 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] In the general formula (15), R １５０ is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and even more preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0543] (First Compound Represented by General Formula (161) or (162)) In the fourth embodiment, the first compound is also preferably a compound represented by the following general formula (161) or the following general formula (162).

[0544]

[0545] (In the general formula (161), Ar １６１is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, m1 is 1, 2, 3, 4, 5, or 6, R １６１ is an electron donating group, R １６１ are respectively Ar １６１ When m1 is 2 or more, a plurality of R １６１ are the same or different, provided that Ar １６１ is not an electron-accepting aromatic hydrocarbon ring or heterocycle, but Ar １６１ In the case where Ar has a substituent, the substituent is not an electron accepting group, and １６２ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, n1 is 1, 2, 3, 4, 5, or 6, and R １６２ is an electron accepting group, and R １６２ are respectively Ar １６２ When n1 is 2 or more, a plurality of R １６２ are the same or different, provided that Ar １６２ is not an electron-donating aromatic hydrocarbon ring or heterocyclic ring, but Ar １６２ When has a substituent, the substituent is not an electron-donating group.

[0546] In the general formulae (161) and (162), Ar １６１ and Ar １６２ are each preferably independently a monovalent or higher valent residue derived from any of the compounds represented by the following general formulas (A61) and (A62).

[0547]

[0548] In the fourth embodiment, R in the general formula (161) １６１ are preferably each independently a monovalent or higher valent residue derived from any of the compounds represented by the following general formulas (DN1) to (DN6) and (DN8) to (DN10), or a group represented by the following general formula (DN7):

[0549]

[0550] (In the general formula (DN7), * represents Ar １６１ It represents the bonding site with the elements that make up the molecule.)

[0551] In the fourth embodiment, R in the general formula (162) １６２ are preferably each independently a monovalent or higher valent residue derived from any of the compounds represented by the following general formulae (AC4) to (AC18) and (AC22) to (AC23), or any of the groups represented by the following general formulae (AC1) to (AC3), (AC19) to (AC21), and (AC24).

[0552]

[0553]

[0554] (In the general formula (AC1), n Ａ is 1, 2 or 3, and in the general formulae (AC22) and (AC23), X １ ~X ８ are each independently CR １６３ or a carbon atom bonded to another atom or structure in the molecule of said first compound, with the proviso that X １ ~X ８ At least one of the carbon atoms in １６２ In the general formula (AC24), X １ ~X ８ are each independently a nitrogen atom or CR １６３ or Ar １６２ In the general formulae (AC22) to (AC24), R １６３ If there are multiple R １６３ are the same or different, and multiple R １６３one 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 １６３ are each independently R in the general formula (102). １２ In the general formulae (AC1) to (AC3), (AC19) to (AC21) and (AC24), * represents Ar １６２ It represents the bonding site with the elements that make up the molecule.)

[0555] In the fourth embodiment, the first compound is also preferably a compound represented by the following general formula (13):

[0556]

[0557] (In the general formula (13), X １３ is an oxygen atom, a sulfur atom, or a group represented by N—Rb, １ ~Z １２ are each independently a nitrogen atom or a group represented by C—Rc, １４ and Ar １５ 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 １４ and L １５ 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; Rb and Rc each independently represent 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 cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —C(═O)R ９０８a group represented by -COOR ９０９ a group represented by -P(=O)(R ９１０ ) (R ９１１ a group represented by —Ge(R ９１２ ) (R ９１３ ) (R ９１４ ) 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 when there are multiple Rc's, the multiple Rc's are the same or different.

[0558] In the compound represented by the general formula (13), -L １４ -Ar １４ and a group represented by -L １５ -Ar １５ and the group represented by １ and Z １２ , Z ２ and Z １１ , Z ３ and Z １０ , Z ４ and Z ９ , Z ５ and Z ８ , and Z ６ and Z ７ In this case, it is also preferable that all of X are not the same group. １３ and a structure fused to the right side of a five-membered ring containing X １３ The compound represented by the general formula (13) is a compound having an asymmetric structure, unlike the structure in which the compound is fused to the left side of a five-membered ring containing the following:

[0559] In the compound represented by the general formula (13), -L １４ -Ar １４ and a group represented by -L １５ -Ar １５ In this case, too, the compound represented by the general formula (13) is a compound having an asymmetric structure, as described above.

[0560] In the fourth embodiment, the first compound is also preferably a compound represented by the following general formula (12):

[0561]

[0562] (In the general formula (12), Ar １１ and Ar １２ 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 １１ and L １２ 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; L １３ is a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring atoms, m is 0, 1, 2, or 3, and a plurality of L １３ are the same or different from each other, and X １ ~X ８ and Y １ ~Y ８ are each independently N or CRa, provided that X ５ ~X ８ One of them and Y １ ~Y ４ One of them is L １３ each Ra is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ), a halogen 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, and when a plurality of Ra's are present, the plurality of Ra's are the same or different from one another, and the compound represented by the general formula (12) satisfies one or both of the following (i) and (ii): (i) Ar １１ and Ar １２At least one of (ii) X is an aryl group substituted with a cyano group and having 6 to 50 ring carbon atoms, or a heterocyclic group substituted with a cyano group and having 5 to 50 ring atoms. １ ~X ４ and Y ５ ~Y ８ At least one of is CRa, and X １ ~X ４ and Y ５ ~Y ８ wherein at least one of Ra is an aryl group substituted with a cyano group and having 6 to 50 ring carbon atoms, or a heterocyclic group substituted with a cyano group and having 5 to 50 ring atoms.

[0563] In the compound represented by the general formula (12), the aromatic hydrocarbon group having 6 to 50 ring carbon atoms and substituted with a cyano group, and the heterocyclic group having 5 to 50 ring atoms and substituted with a cyano group may further have a substituent other than a cyano group.

[0564] In the compound represented by the general formula (12), m is preferably 0, 1 or 2, and more preferably 0 or 1. In the compound represented by the general formula (12), when m is 0, X ５ ~X ８ One of them and Y １ ~Y ４ is directly bonded to one of the groups via a single bond.

[0565] In the compound represented by the general formula (12), X ６ and Y ３ Pair with X ６ and Y ２ Pairs with and X ７ and Y ３ Any pair selected from the group consisting of pairs of １３ It is preferable that the carbon atom is bonded via a carbon atom bonded directly to the carbon atom.

[0566] X ６ and Y ３ The pair with L １３ When the carbon atom is bonded via an intervening group or is bonded directly, the compound represented by the general formula (12) is represented by the following general formula (121).

[0567]

[0568] (In the general formula (121), Ar １１ , Ar １２ , L １１ , L １２ , L １３ , m, X １ ~X ５ , X ７ ~X ８ , Y １ ~Y ２ and Y ４ ~Y ８ respectively represent Ar in the general formula (12) １１ , Ar １２ , L １１ , L １２ , L １３ , m, X １ ~X ５ , X ７ ~X ８ , Y １ ~Y ２ and Y ４ ~Y ８ and the compound represented by the general formula (121) satisfies at least one of the conditions (i) and (ii).

[0569] In the compound represented by the general formula (12), -Ar １１ -L １１ and a group represented by -Ar １２ -L １２ and the groups represented by the following formula (I) are preferably different from each other.

[0570] L １３ The monocyclic hydrocarbon group having 6 or less ring carbon atoms as L is preferably at least one group selected from the group consisting of a phenylene group, a cyclopentenylene group, a cyclopentadienylene group, a cyclohexylene group, and a cyclopentylene group, and more preferably a phenylene group. １３ The monocyclic heterocyclic group having 6 or less ring atoms as represented by is preferably at least one group selected from the group consisting of a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a furylene group, and a thiophenylene group.

[0571] In one embodiment, the light-emitting layer may contain two or more first compounds having different molecular structures. By mixing compounds with different charge transport properties, the charge balance in the light-emitting layer is improved, and improvement in luminous efficiency is expected. Furthermore, by forming an exciplex between two or more first compounds (host materials), excitation energy is reduced, enabling lower voltage driving than when a single host material is contained in the light-emitting layer.

[0572] (Method for Producing First Compound (Compound M1)) The first compound (Compound M1) can be produced by a known method. The first compound can also be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0573] (Specific Examples of the First Compound (Compound M1)) Specific examples of the first compound (compound M1) of the fourth embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

[0574]

[0575]

[0576]

[0577]

[0578]

[0579]

[0580]

[0581]

[0582]

[0583]

[0584]

[0585]

[0586]

[0587]

[0588]

[0589]

[0590]

[0591]

[0592]

[0593]

[0594]

[0595]

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602]

[0603]

[0604]

[0605]

[0606]

[0607]

[0608]

[0609]

[0610]

[0611]

[0612]

[0613]

[0614]

[0615]

[0616]

[0617]

[0618]

[0619]

[0620]

[0621]

[0622]

[0623]

[0624]

[0625]

[0626]

[0627]

[0628]

[0629]

[0630]

[0631]

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[0634]

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[0641]

[0642]

[0643]

[0644]

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[0651]

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[0653]

[0654]

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[0656]

[0657]

[0658]

[0659]

[0660]

[0661]

[0662] (Relationship between host material, sensitizer material, and fluorescent material in the light-emitting layer) In one embodiment, the sensitizer material is the delayed fluorescent compound. In one embodiment, the light-emitting layer contains the delayed fluorescent compound as a sensitizer material, but does not contain a phosphorescent metal complex.

[0663] FIG. 5 is a diagram showing an example of the relationship between the energy levels of a host material, a sensitizing material, and a fluorescent material when an emitting layer contains a host material (first compound (compound M1)), a delayed fluorescent compound as a sensitizing material (second compound (compound M2)), and a fluorescent material (third compound (compound M3)). In FIG. 5 , S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the host material, and T1(M1) represents the lowest excited triplet state of the host material. S1(M2) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M2) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M2) to S1(M3) in FIG. 5 represents Förster energy transfer from the lowest excited singlet state of the delayed fluorescent compound to the lowest excited singlet state of the fluorescent material. As shown in FIG. 5, when a compound with a small ΔST(M2) is used as the delayed fluorescent compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, Förster energy transfer occurs from the lowest excited singlet state S1(M2) of the delayed fluorescent compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing delayed fluorescence due to this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0664] In one embodiment, the energy gap T at 77 K of the host material ７７Ｋ (M1) and the energy gap T of the sensitizing material at 77 [K] ７７Ｋ (M2) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1): T７７Ｋ (M1) > T ７７Ｋ (M2) ...(Math. 1)

[0665] In one embodiment, the lowest excited singlet energy S of the host material １ (M1) and the lowest excited singlet energy S of the sensitizing material １ It is also preferable that (M2) satisfies the relationship of the following mathematical formula (Mathematical Formula 4A): S １ (M1) > S １ (M2) ...(Math 4A)

[0666] In one embodiment, the lowest excited singlet energy S of the host material, the sensitizing material, and the fluorescent material １ It is also preferable that S satisfies the relationship of the following mathematical formula (Mathematical Formula 4B): １ (M1) > S １ (M2) > S １ (M3) ... (Math 4B)

[0667] In one embodiment, the energy gap T at 77 [K] of the host material, the sensitizing material, and the fluorescent material ７７Ｋ It is also preferable that T satisfies the relationship of the following formula (Formula 6B): ７７Ｋ (M1) > T ７７Ｋ (M2) > T ７７Ｋ (M3) ...(Number 6B)

[0668] (Compound Content in Emitting Layer) The contents of the host material (compound M1), sensitizing material (compound M2), and fluorescent material (compound M3) contained in the emitting layer are preferably within the following ranges, for example. The content of the host material (compound M1) in the emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more. The content of the host material (compound M1) in the emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.

[0669] The content of the sensitizing material (compound M2) is preferably 5% by mass or more, more preferably 10% by mass or more, and is preferably 50% by mass or less, more preferably 30% by mass or less.

[0670] The content of the fluorescent material (compound M3) in the light-emitting layer is preferably 0.5% by mass or more, more preferably 1% by mass or more. The content of the fluorescent material (compound M3) in the light-emitting layer is preferably 10% by mass or less, more preferably 5% by mass or less. The upper limit of the total content of the host material (compound M1), sensitizing material (compound M2), and fluorescent material (compound M3) in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the case where the light-emitting layer contains materials other than the host material, sensitizing material, and fluorescent material. In this embodiment, the light-emitting layer may contain only one type of host material, or may contain two or more types of host materials.

[0671] In the organic EL element according to the fourth embodiment, the light-emitting layer contains the compound according to the first embodiment (compound M3 (third compound)), and therefore, according to the fourth embodiment, the luminous efficiency of the organic EL element can be improved. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0672] [Fifth Embodiment] The configuration of an organic EL element according to a fifth embodiment will be described. In the description of the fifth embodiment, the same components as those in the third embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the fifth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third and fourth embodiments can be used.

[0673] The organic EL element according to the fifth embodiment differs from the organic EL elements according to the third and fourth embodiments in that the light-emitting layer contains a phosphorescent metal complex, but is otherwise similar to the organic EL elements according to the third and fourth embodiments.

[0674] An organic EL device according to a fifth embodiment includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode, and the emitting layer may include a phosphorescent metal complex as a sensitizer material and a fluorescent material (compound M3 (third compound)) as a dopant material. An organic EL device according to one embodiment includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode, and the emitting layer may include a first compound as a host material, a phosphorescent metal complex as a sensitizer material, and a fluorescent material (third compound (compound M3)) as a dopant material.

[0675] (Phosphorescent Metal Complex) In one embodiment, the phosphorescent metal complex preferably contains a heavy metal atom.

[0676] In one embodiment, the phosphorescent metal complex preferably contains one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0677] In one embodiment, the phosphorescent metal complex is preferably a compound represented by the following general formula (21): M(L １ ) ｎ１ (L ２ ) ｎ２ …(21)

[0678]

[0679] In the general formulas (21), (211), (212), and (213), M is a transition metal selected from the group consisting of first transition metals, second transition metals, and third transition metals; L １ is at least one ligand selected from the group consisting of a ligand represented by the general formula (211), a ligand represented by the general formula (212), and a ligand represented by the general formula (213), n1 is 1, 2, or 3, L ２is at least one ligand selected from the group consisting of monodentate, bidentate and tridentate ligands; n2 is 0, 1, 2, 3 or 4; CY １ Tamaki, C.Y. ２ Tamaki, C.Y. ３ Ring and CY ４ each ring is independently selected from the group consisting of a carbocyclic group having 5 to 30 ring carbon atoms and a heterocyclic group having 1 to 30 ring carbon atoms; １ ~Y ４ are each independently a single bond, a double bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, *a-O-*b, *a-S-*b, *a-C(=O)-*b, *a-S(=O)-*b, *a-C(R ５ ) (R ６ )-*b, *a-C(R ５ ) = C(R ６ )-*b, *a-C(R ５ )=*b, *a-Si(R ５ ) (R ６ )-*b, *a-B(R ５ )-*b, *a-N(R ５ )-*b, and *a-P(R ５ a1, a2, and a3 are each independently 1, 2, or 3; a4 is 0, 1, 2, or 3; and when a4 is 0, CY １ Ring and CY ４ The rings are not connected to each other, and １ , T ２ , T ３ and T ４ are each independently a chemical bond, *a-O-*b, *a-S-*b, *a-B(R ７ )-*b, *a-N(R ７ )-*b, *a-P(R ７ )-*b, *a-C(R ７ ) (R ８ )-*b, *a-Si(R ７ ) (R ８)-*b, *a-Ge(R ７ ) (R ８ *a and *b are each independently a bonding position to an adjacent atom, *1, *2, *3 and *4 are bonding positions to M, and R １ ~R ８ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, a substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms, 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, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si(R ２５１ ) (R ２５２ ) (R ２５３ a group represented by —O—(R ２５４ ), a group represented by —S—(R ２５５ a group represented by —N(R ２５６ ) (R ２５７ a group represented by —C(═O)R ２５８ a group represented by —C(═O)(OR ２５９ a group represented by —S(═O) ２ (OR ２６０ ), a group represented by —O—P(═O)(OR ２６１ ) (OR ２６２ ), a group represented by —C(R ２６３ ) (R ２６４ ) (R ２６５ ), a group represented by —B(R ２６６ ) (R２６７ a group represented by —P(R ２６８ ) (R ２６９ ), a group represented by —S(═O)(R ２７０ a group represented by —S(═O) ２ (R ２７１ ), a group represented by —P(═O)(R ２７２ ) (R ２７３ ) and a group represented by —P(═S)(R ２７４ ) (R ２７５ R １ ~R ８ 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, １ ~R ８ , and Y １ ~Y ４ one or more pairs of adjacent two or more of the following are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other; b1, b2, b3, and b4 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; R ２５１ ~R ２７５ are each independently a hydrogen atom, a halogen atom, or —O—(R ２７６ a group represented by —N(R ２７７ ) (R ２７８), a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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, a substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R is selected from the group consisting of a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a biphenylyl group, and a terphenylyl group; ２７６ ~R ２７８ 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.

[0680] As used herein, a carbocyclic group having 5 to 30 ring carbon atoms refers to a monocyclic or polycyclic group having 5 to 30 ring carbon atoms containing only carbon as ring atoms. The carbocyclic group having 5 to 30 ring carbon atoms may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The carbocyclic group having 5 to 30 ring carbon atoms may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, depending on the number of substituents bonded to the carbocyclic group having 5 to 30 ring carbon atoms, various modifications are possible, such as a trivalent group or a tetravalent group.

[0681] In this specification, a heterocyclic group having 1 to 30 ring carbon atoms refers to a group which has the same structure as a carbocyclic group having 5 to 30 ring carbon atoms, but which contains, as a ring-forming atom, at least one heteroatom selected from N (nitrogen atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom) and S (sulfur atom) in addition to carbon (which may have 1 to 30 carbon atoms).

[0682] In this specification, a heterocycloalkyl group having 3 to 50 ring atoms means a monovalent monocyclic group having 3 to 50 ring atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom, and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. In this specification, a heterocycloalkylene group having 3 to 50 ring atoms means a divalent group having the same structure as a heterocycloalkyl group having 3 to 50 ring atoms.

[0683] In this specification, a cycloalkenyl group having 3 to 50 ring carbon atoms refers to a monovalent monocyclic group having 3 to 50 ring carbon atoms and having at least one double bond in the ring but not having aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. In this specification, a cycloalkenylene group having 3 to 50 ring carbon atoms refers to a divalent group having the same structure as a cycloalkenyl group having 3 to 50 ring carbon atoms.

[0684] As used herein, a heterocycloalkenyl group having 3 to 50 ring atoms is a monovalent monocyclic group having 3 to 50 ring atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom, and having at least one double bond within the ring. Specific examples of heterocycloalkenyl groups having 3 to 50 ring atoms include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. As used herein, a heterocycloalkenylene group having 3 to 50 ring atoms refers to a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring atoms.

[0685] According to one embodiment, in the compound represented by general formula (21), the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms, the substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms, the substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms, and the substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms.

[0686] As used herein, a monovalent non-aromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are fused together, which contains only carbon as ring-forming atoms, and the entire molecule has non-aromaticity. As used herein, a divalent non-aromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

[0687] In this specification, a monovalent non-aromatic hetero-fused polycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are fused together and which contains, in addition to carbon as ring-forming atoms, at least one heteroatom selected from N, O, Si, P, and S, and the entire molecule is non-aromatic. In this specification, a divalent non-aromatic hetero-fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic hetero-fused polycyclic group.

[0688] In this specification, the term "biphenylyl group" refers to a "phenyl group substituted with a phenyl group." The "biphenylyl group" belongs to the category of "substituted phenyl groups" whose substituent is an "aryl group having 6 to 50 ring carbon atoms."

[0689] In this specification, the term "terphenylyl group" refers to a "phenyl group substituted with a biphenylyl group." The "terphenylyl group" belongs to the "substituted phenyl group" whose substituent is an "aryl group having 6 to 50 ring carbon atoms substituted with an aryl group having 6 to 50 ring carbon atoms."

[0690] In the compound represented by the general formula (21), T １ , T ２ , T ３ and T ４ The chemical bond as is preferably a single bond.

[0691] In the compound represented by the general formula (21), M is preferably one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm), and more preferably platinum (Pt) or iridium (Ir).

[0692] According to one embodiment, in the compound represented by the general formula (21), CY １ Ring ~ CY ４The rings each independently represent benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenophene, indole, benzoborol, benzophosphole, indene, benzosilole, benzogermole, benzothiophene, benzoselenophene, benzofuran, carbazole, dibenzoborol, dibenzophosphole, fluorene, dibenzosilole, dibenzogermole, dibenzothiophene, dibenzoselenophene, dibenzofuran, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindole, azabenzoborole, azabenzophosphole, azaindene, azabenzosilole, azabenzogermole, azabenzothiophene, azabenzoselenophene, azabenzofuran, The compound may be selected from the group consisting of azacarbazole, azadibenzoborole, azadibenzophosphole, azafluorene, azadibenzosilole, azadibenzogermole, azadibenzothiophene, azadibenzoselenophene, azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

[0693] According to one embodiment, CY in general formula (211) １ Ring and CY ２ At least one of the rings, CY in general formula (212) １ Ring ~ CY ３ At least one of the rings, and CY in general formula (213) １ Ring ~ CY ４At least one of the rings may be a carbene.

[0694] According to one embodiment, Y in the general formulae (211) to (213) １ ~Y ４ are each independently a single bond, a double bond, *a-O-*b, *a-S-*b, *a-C(R ５ ) (R ６ )-*b and *a-N(R ５ )-*b.

[0695] According to one embodiment, in general formula (211), R １ and R ２ In the general formula (212), R １ ~R ３ and in the general formula (213), R １ ~R ４ At least one of the groups may be an electron donating group.

[0696] For example, the electron-donating group may be a substituent selected from the group consisting of an isopropyl group, a tert-butyl group, and the following general formulae (10-1) to (10-61).

[0697]

[0698]

[0699] In the general formulae (10-1) to (10-61), * indicates the bonding position to the adjacent atom.

[0700] In this specification, a deuterium atom is represented as D in a chemical formula, and a proton atom is represented as H or is omitted. In this specification, a methyl group may be represented as Me, a phenyl group as Ph, an isopropyl group as i-Pr, and a t-butyl group as t-Bu in a chemical formula.

[0701] According to one embodiment, R in the general formula (211) １ and R ２ and / or at least one of Y １is *a-N(R ５ ) - * b, and R ５ may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0702] According to one embodiment, R in the general formula (212) １ ~R ３ and / or at least one of Y １ and Y ２ At least one of *a-N(R ５ ) - * b, and R ５ may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0703] According to one embodiment, R in the general formula (213) １ ~R ４ and / or at least one of Y １ ~Y ４ At least one of *a-N(R ５ ) - * b, and R ５ may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0704] The light-emitting layer contains the compound according to the first embodiment (compound M3 (third compound)) and a phosphorescent metal complex as a sensitizing material, thereby improving the luminous efficiency of the organic EL device. The organic EL device according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0705] In the organic EL element according to the fifth embodiment, the light-emitting layer contains the compound according to the first embodiment (compound M3 (third compound)), and therefore, according to the fifth embodiment, the performance of the organic EL element can be improved. The organic EL element according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0706] Sixth Embodiment (Electronic Device) An electronic device according to a sixth embodiment is equipped with an organic EL element according to any of the embodiments described in this specification. The electronic device according to the sixth embodiment may be equipped with an organic EL element according to any of the other embodiments described below. 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), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting. The light-emitting device can be used in a display device, for example, as a backlight for a display device.

[0707] The display device as the electronic device according to the sixth embodiment is preferably an organic EL display device having organic EL elements as red, green, and blue pixels, and the blue pixels are preferably at least one of the organic EL elements according to the third or fourth embodiment and the modified examples described below.

[0708] [Modifications of the Embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.

[0709] For example, the number of light-emitting layers is not limited to one, and multiple light-emitting layers may be stacked. When the organic EL element has multiple light-emitting layers, it is sufficient that at least one of the light-emitting layers satisfies the conditions described in the above embodiment. For example, the other light-emitting layers 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 intermediate layer.

[0710] 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.

[0711] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope that the object of the present invention can be achieved.

[0712] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0713] <Compounds> The structures of the compounds represented by general formula (1) used in the production of the organic EL devices according to Examples 1 to 11 are shown below.

[0714]

[0715]

[0716]

[0717] The structure of the comparative compound used in the production of the organic EL device according to Comparative Example 1 is shown below.

[0718]

[0719] The structures of the reference compounds used in the production of the organic EL devices according to Reference Examples 1 and 2 are shown below.

[0720]

[0721] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 11, Comparative Example 1, and Reference Examples 1 and 2 are shown below.

[0722]

[0723]

[0724] <Preparation of Organic EL Device> An organic EL device was prepared as follows and evaluated.

[0725] Example 1 A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness 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 HT-1 and compound HI-1 were co-deposited on the surface on which the transparent electrode lines were formed, covering the transparent electrode, to form a hole injection layer with a film thickness of 10 nm. The proportion of compound HT-1 in the hole injection layer was 97% by mass, and the proportion of compound HI-1 was 3% by mass. Next, compound HT-1 was vapor-deposited on the hole injection layer to form a first hole transport layer with a film thickness of 80 nm. Next, compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Next, compound EBL-1 was evaporated on the second hole-transporting layer to form a third hole-transporting layer (also referred to as an electron blocking layer) with a thickness of 5 nm. Next, compound HOST-1 as a host material (first compound), compound STZ-1 as a sensitizing material (delayed fluorescent compound, second compound), and compound BD-1 as a fluorescent material (third compound) were co-evaporated on the third hole-transporting layer to form an emitting layer with a thickness of 30 nm. The proportion of compound HOST-1 in the emitting layer was 74 mass%, the proportion of compound STZ-1 was 25 mass%, and the proportion of compound BD-1 was 1 mass%. Next, compound HBL-1 was evaporated on the emitting layer to form a hole-blocking layer with a thickness of 10 nm. Next, compound ET-1 was evaporated on the hole-blocking layer to form an electron-transporting layer with a thickness of 20 nm. Next, LiF was evaporated on the electron-transporting layer to form an electron-injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on the electron injection layer to form a metallic Al cathode with a film thickness of 50 nm. In this manner, the organic EL element according to Example 1 was fabricated. The element configuration of the organic EL element according to Example 1 is schematically shown as follows.ITO(130) / HT-1:HI-1(10,97%:3%) / HT-1(80) / HT-2(5) / EBL-1(5) / HOST-1:STZ-1:BD-1(30,74%:25%:1%) / HBL-1(10) / ET-1(20) / LiF(1) / Al(50) Note that in the above device configuration, the numbers in parentheses indicate film thickness (unit: nm). Similarly, in the above device configuration, the numbers in parentheses expressed as percentages (97%:3%) indicate the proportions (mass%) of Compound HT-1 and Compound HI-1 in the hole injection layer, and the numbers expressed as percentages (74%:25%:1%) indicate the proportions (mass%) of Compound HOST-1, Compound STZ-1, and Compound BD-1 in the light-emitting layer.

[0726] Examples 2 to 11 The organic EL devices of Examples 2 to 11 were fabricated in the same manner as in Example 1, except that the compound BD-1 used as the fluorescent material (third compound) in the emitting layer of Example 1 was changed to each of the compounds shown in Table 1.

[0727] Comparative Example 1 The organic EL element of Comparative Example 1 was produced in the same manner as in Example 1, except that the compound BD-1 used as the fluorescent material in the emitting layer of Example 1 was changed to a compound shown in Table 1.

[0728] (Reference Examples 1 and 2) The organic EL devices of Reference Examples 1 and 2 were prepared in the same manner as in Example 1, except that the compound BD-1 used as the fluorescent material in the emitting layer of Example 1 was changed to each of the compounds shown in Table 1.

[0729] <Evaluation of Organic EL Devices> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 1. Table 1 also shows the evaluation results of the compounds used in the light-emitting layer of each of the Examples, Comparative Examples, and Reference Examples.

[0730] (External quantum efficiency EQE) The fabricated organic EL element was applied with a current density of 10.00 mA / cm ２The spectral radiance spectrum when a voltage was applied so that the value was 0.01 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed. Table 1 shows the relative values ​​of EQE. Based on the EQE of each example of Examples 1 to 11, Comparative Example 1, and Reference Examples 1 and 2, and the following mathematical formula (Math. 1X), the "EQE (relative value)" (unit: %) was calculated. EQE (relative value) = (EQE of each example / EQE of Comparative Example 1) × 100 (Math. 1X)

[0731]

[0732] As shown in Table 1, the organic EL elements of Examples 1 to 11 contained a sensitizing material and a fluorescent material represented by general formula (1) in the light-emitting layer, and emitted light with higher efficiency than the organic EL element of Comparative Example 1.

[0733] <Synthesis Examples> [Synthesis Example 1: Synthesis of Compound BD-1] Compound BD-1 was synthesized according to the following synthesis route.

[0734]

[0735] (1-1) Synthesis of Intermediate M1-3 Under an argon atmosphere, a solution of intermediate M1-1 (7.85 g, 31.8 mmol), intermediate M1-2 (8.21 g, 31.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.582 g, 0.635 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.735 g, 1.30 mmol), and sodium tert-butoxide (4.27 g, 44.5 mmol) in toluene (160 mL) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M1-3 (9.58 g, 71% yield).

[0736]

[0737] (1-2) Synthesis of Intermediate M1-5 Under an argon atmosphere, a toluene (30 mL) solution of intermediate M1-3 (7.85 g, 18.5 mmol), intermediate M1-4 (2.50 g, 9.25 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.169 g, 0.185 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.214 g, 0.370 mmol), and sodium tert-butoxide (2.67 g, 27.7 mmol) was heated and stirred at 100°C for 8 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M1-5 (4.60 g, 52% yield).

[0738]

[0739] (1-3) Synthesis of Compound BD-1 Under an argon atmosphere, a solution of intermediate M1-5 (4.00 g, 4.18 mmol) in tert-butylbenzene (20 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (5.3 mL, 1.6 M, 8.52 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (4.19 g, 16.7 mmol) and diisopropylethylamine (1.08 g, 8.36 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off. The resulting crude product was purified by column chromatography and recrystallization to obtain Compound BD-1 (1.05 g, 27% yield). The molecular weight of Compound BD-1 was 930, and the mass spectrum analysis result of the obtained compound showed an m / z (mass-to-charge ratio) = 930, indicating that it was identified as Compound BD-1.

[0740] Synthesis Example 2: Synthesis of Compound BD-2 Compound BD-2 was synthesized according to the following synthesis route.

[0741]

[0742] (2-1) Synthesis of Intermediate M2-2 Under an argon atmosphere, a solution of intermediate M2-1 (6.38 g, 25.8 mmol), intermediate M1-2 (6.67 g, 25.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.473 g, 0.516 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.598 g, 1.03 mmol), and sodium tert-butoxide (3.47 g, 36.1 mmol) in toluene (130 mL) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M2-2 (8.77 g, 80% yield).

[0743]

[0744] (2-2) Synthesis of Intermediate M2-3 Under an argon atmosphere, a toluene (30 mL) solution of intermediate M2-2 (6.91 g, 16.3 mmol), intermediate M1-4 (2.20 g, 8.14 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.149 g, 0.163 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.188 g, 0.326 mmol), and sodium tert-butoxide (2.35 g, 24.4 mmol) was heated and stirred at 100°C for 9 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M2-3 (3.66 g, 47% yield).

[0745]

[0746] (2-3) Synthesis of Compound BD-2 Under an argon atmosphere, a tertiary butylbenzene (20 mL) solution of intermediate M2-3 (3.50 g, 3.66 mmol) was cooled to −78°C, and then a pentane solution of tertiary butyllithium (4.7 mL, 1.6 M, 7.46 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (3.66 g, 14.6 mmol) and diisopropylethylamine (0.945 g, 7.31 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography and recrystallization to obtain Compound BD-2 (1.12 g, yield 33%). The molecular weight of compound BD-2 was 930, and the mass spectrum analysis result of the obtained compound showed m / z (mass-to-charge ratio) = 930, so that it was identified as compound BD-2.

[0747] Synthesis Example 3: Synthesis of compound BD-3 Compound BD-3 was synthesized according to the following synthesis route.

[0748]

[0749] (3-1) Synthesis of Intermediate M3-2 Under an argon atmosphere, a solution of intermediate M3-1 (6.78 g, 27.4 mmol), intermediate M1-2 (7.09 g, 27.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.503 g, 0.549 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.635 g, 1.10 mmol), and sodium tert-butoxide (3.69 g, 38.4 mmol) in toluene (140 mL) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, the organic layer was separated, and then purified by column chromatography to obtain intermediate M3-2 (8.04 g, yield 69%).

[0750]

[0751] (3-2) Synthesis of Intermediate M3-3 Under an argon atmosphere, a toluene (30 mL) solution of intermediate M3-2 (7.85 g, 18.5 mmol), intermediate M1-4 (2.50 g, 9.25 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.169 g, 0.185 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.214 g, 0.370 mmol), and sodium tert-butoxide (2.67 g, 27.7 mmol) was heated and stirred at 100°C for 8 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M3-3 (4.34 g, 49% yield).

[0752]

[0753] (3-3) Synthesis of Compound BD-3 Under an argon atmosphere, a solution of intermediate M3-3 (3.80 g, 3.97 mmol) in tert-butylbenzene (20 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (5.1 mL, 1.6 M, 8.10 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (3.98 g, 15.9 mmol) and diisopropylethylamine (1.03 g, 7.94 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off. The resulting crude product was purified by column chromatography and recrystallization to obtain Compound BD-3 (1.03 g, 28% yield). The molecular weight of Compound BD-3 was 930, and the mass spectrum analysis result of the obtained compound showed an m / z (mass-to-charge ratio) = 930, indicating that it was identified as Compound BD-3.

[0754] Synthesis Example 4: Synthesis of compound BD-4 Compound BD-4 was synthesized according to the following synthesis route.

[0755]

[0756] (4-1) Synthesis of Intermediate M4-2 Under an argon atmosphere, a solution of intermediate M3-1 (7.12 g, 28.8 mmol), intermediate M4-1 (7.68 g, 28.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.528 g, 0.576 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.667 g, 1.15 mmol), and sodium tert-butoxide (3.88 g, 40.3 mmol) in toluene (150 mL) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, the organic layer was separated, and then purified by column chromatography to obtain intermediate M4-2 (9.22 g, yield 74%).

[0757]

[0758] (4-2) Synthesis of Intermediate M4-3 Under an argon atmosphere, a solution of intermediate M4-2 (8.80 g, 20.3 mmol), intermediate M1-4 (2.75 g, 10.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.186 g, 0.203 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.235 g, 0.407 mmol), and sodium tert-butoxide (2.93 g, 30.5 mmol) in toluene (35 mL) was heated and stirred at 100°C for 7 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M4-3 (4.56 g, 46% yield).

[0759]

[0760] (4-3) Synthesis of Compound BD-4 Under an argon atmosphere, a solution of intermediate M4-3 (4.23 g, 4.34 mmol) in tert-butylbenzene (22 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (5.5 mL, 1.6 M, 8.86 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (4.35 g, 17.4 mmol) and diisopropylethylamine (1.12 g, 8.69 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off. The resulting crude product was purified by column chromatography and recrystallization to obtain Compound BD-4 (1.23 g, 30% yield). The molecular weight of Compound BD-4 was 946, and the mass spectrum analysis result of the obtained compound showed an m / z (mass-to-charge ratio) = 946, indicating that it was identified as Compound BD-4.

[0761] Synthesis Example 5: Synthesis of compound BD-5 Compound BD-5 was synthesized according to the following synthesis route.

[0762]

[0763] (5-1) Synthesis of Intermediate M5-2 Under an argon atmosphere, a toluene (35 mL) solution of intermediate M3-2 (8.06 g, 19.0 mmol), intermediate M5-1 (2.70 g, 9.49 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.174 g, 0.190 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.220 g, 0.380 mmol), and sodium tert-butoxide (2.74 g, 28.5 mmol) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M5-2 (5.07 g, 55% yield).

[0764]

[0765] (5-2) Synthesis of Compound BD-5 Under an argon atmosphere, a solution of intermediate M5-2 (4.30 g, 4.43 mmol) in tert-butylbenzene (22 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (5.6 mL, 1.6 M, 9.03 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (4.44 g, 17.7 mmol) and diisopropylethylamine (1.14 g, 8.85 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off. The resulting crude product was purified by column chromatography and recrystallization to obtain Compound BD-5 (1.51 g, 36% yield). The molecular weight of Compound BD-5 was 944, and the mass spectrum analysis result of the obtained compound showed an m / z (mass-to-charge ratio) = 944, indicating that it was identified as Compound BD-5.

[0766] Synthesis Example 6: Synthesis of compound BD-6 Compound BD-6 was synthesized according to the following synthesis route.

[0767]

[0768] (6-1) Synthesis of Intermediate M6-2 Under an argon atmosphere, a toluene (120 mL) solution of intermediate M6-1 (7.75 g, 24.0 mmol), intermediate M1-2 (6.19 g, 24.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.439 g, 0.480 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.555 g, 0.959 mmol), and sodium tert-butoxide (3.23 g, 33.6 mmol) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M6-2 (7.44 g, yield 62%).

[0769]

[0770] (6-2) Synthesis of Intermediate M6-3 Under an argon atmosphere, a toluene (23 mL) solution of intermediate M6-2 (6.87 g, 13.7 mmol), intermediate M5-1 (1.95 g, 6.86 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.126 g, 0.137 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.159 g, 0.274 mmol), and sodium tert-butoxide (1.98 g, 20.6 mmol) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M6-2 (2.93 g, yield 38%).

[0771]

[0772] (6-3) Synthesis of Compound BD-6 Under an argon atmosphere, a solution of intermediate M6-2 (2.75 g, 2.45 mmol) in tert-butylbenzene (12 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (3.1 mL, 1.6 M, 4.99 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (2.45 g, 9.79 mmol) and diisopropylethylamine (0.633 g, 4.89 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography and recrystallization to obtain Compound BD-6 (1.51 g, yield 36%). The molecular weight of compound BD-6 was 1097, and the mass spectrum analysis result of the obtained compound showed m / z (mass-to-charge ratio) = 1097, so that it was identified as compound BD-6.

[0773] Synthesis Example 7: Synthesis of compound BD-7 Compound BD-7 was synthesized according to the following synthesis route.

[0774]

[0775] (7-1) Synthesis of Intermediate M7-2 Under an argon atmosphere, a solution of intermediate M7-1 (7.60 g, 23.7 mmol), intermediate M5-1 (8.41 g, 29.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.542 g, 0.591 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.684 g, 1.18 mmol), and sodium tert-butoxide (3.98 g, 41.4 mmol) in toluene (200 mL) was heated and stirred at 100°C for 5 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M7-2 (8.85 g, 57% yield).

[0776]

[0777] (7-2) Synthesis of Intermediate M7-3 Under an argon atmosphere, a solution of intermediate M7-2 (5.65 g, 10.8 mmol), intermediate M3-2 (5.03 g, 11.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.197 g, 0.215 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.249 g, 0.431 mmol), and sodium tert-butoxide (1.45 g, 15.1 mmol) in toluene (36 mL) was heated and stirred at 100°C for 5 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M7-3 (7.01 g, 75% yield).

[0778]

[0779] (7-3) Synthesis of Compound BD-7 Under an argon atmosphere, a solution of intermediate M7-3 (5.00 g, 5.76 mmol) in tert-butylbenzene (30 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (7.3 mL, 1.6 M, 11.7 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (5.77 g, 23.0 mmol) and diisopropylethylamine (1.49 g, 11.5 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography and recrystallization to obtain Compound BD-7 (1.79 g, yield 37%). The molecular weight of Compound BD-7 was 841, and the mass spectrum analysis result of the obtained compound showed an m / z (mass-to-charge ratio) = 841, indicating that it was identified as Compound BD-7.

[0780] Synthesis Example 8: Synthesis of compound BD-8 Compound BD-8 was synthesized according to the following synthesis route.

[0781]

[0782] (8-1) Synthesis of Intermediate M8-2 Under an argon atmosphere, a toluene (35 mL) solution of intermediate M3-2 (9.00 g, 21.2 mmol), intermediate M8-1 (3.46 g, 10.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.194 g, 0.212 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.245 g, 0.424 mmol), and sodium tert-butoxide (3.06 g, 31.8 mmol) was heated and stirred at 100°C for 7 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M8-2 (6.23 g, yield 58%).

[0783]

[0784] (8-2) Synthesis of Compound BD-8 Under an argon atmosphere, a solution of intermediate M8-2 (5.11 g, 5.04 mmol) in tert-butylbenzene (25 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (6.4 mL, 1.6 M, 10.3 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (5.05 g, 20.2 mmol) and diisopropylethylamine (1.30 g, 10.1 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off. The resulting crude product was purified by column chromatography and recrystallization to obtain Compound BD-8 (1.59 g, 32% yield). The molecular weight of Compound BD-8 was 986, and the mass spectrum analysis result of the obtained compound showed an m / z (mass-to-charge ratio) = 986, indicating that it was identified as Compound BD-8.

[0785] Synthesis Example 9: Synthesis of compound BD-9 Compound BD-9 was synthesized according to the following synthesis route.

[0786]

[0787] (9-1) Synthesis of Intermediate M9-2 Under an argon atmosphere, a toluene (30 mL) solution of intermediate M9-1 (4.89 g, 9.28 mmol), intermediate M2-2 (4.33 g, 10.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.170 g, 0.186 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.215 g, 0.371 mmol), and sodium tert-butoxide (1.25 g, 13.0 mmol) was heated and stirred at 100°C for 4 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M9-2 (5.90 g, 73% yield).

[0788]

[0789] (9-2) Synthesis of Compound BD-9 Under an argon atmosphere, a solution of intermediate M9-2 (4.89 g, 5.62 mmol) in tert-butylbenzene (30 mL) was cooled to −78°C, and then a pentane solution of tert-butyllithium (7.2 mL, 1.6 M, 11.5 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (5.64 g, 22.5 mmol) and diisopropylethylamine (1.46 g, 11.3 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off. The resulting crude product was purified by column chromatography and recrystallization to obtain Compound BD-9 (1.85 g, 39% yield). The molecular weight of Compound BD-9 was 843, and the mass spectrum analysis result of the obtained compound showed an m / z (mass-to-charge ratio) = 843, indicating that it was identified as Compound BD-9.

[0790] Synthesis Example 10: Synthesis of compound BD-10 Compound BD-10 was synthesized according to the following synthesis route.

[0791]

[0792] (10-1) Synthesis of Intermediate M10-2 Under an argon atmosphere, a solution of intermediate M10-1 (6.89 g, 21.3 mmol), intermediate M1-2 (5.51 g, 21.3 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.390 g, 0.426 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.493 g, 0.853 mmol), and sodium tert-butoxide (2.87 g, 29.8 mmol) in toluene (110 mL) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M10-2 (6.94 g, yield 65%).

[0793]

[0794] (10-2) Synthesis of Intermediate M10-3 Under an argon atmosphere, a toluene (20 mL) solution of intermediate M10-2 (6.29 g, 12.6 mmol), intermediate M8-1 (2.05 g, 6.28 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.115 g, 0.126 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.145 g, 0.251 mmol), and sodium tert-butoxide (1.81 g, 18.8 mmol) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M10-3 (3.00 g, 41% yield).

[0795]

[0796] (10-3) Synthesis of Compound BD-10 Under an argon atmosphere, a solution of intermediate M10-3 (2.65 g, 2.27 mmol) in tert-butylbenzene (11 mL) was cooled to -78°C, and then a pentane solution of tert-butyllithium (2.9 mL, 1.6 M, 4.64 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (2.28 g, 9.09 mmol) and diisopropylethylamine (0.588 g, 4.55 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography and recrystallization to obtain Compound BD-10 (0.647 g, yield 25%). The molecular weight of compound BD-10 was 1138, and the mass spectrum analysis result of the obtained compound showed m / z (mass-to-charge ratio) = 1138, so that the compound was identified as compound BD-10.

[0797] Synthesis Example 11: Synthesis of compound BD-11 Compound BD-11 was synthesized according to the following synthesis route.

[0798]

[0799] (11-1) Synthesis of Intermediate M11-3 Under an argon atmosphere, a toluene (80 mL) solution of intermediate M11-1 (5.31 g, 15.9 mmol), intermediate M11-2 (2.91 g, 15.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.291 g, 0.318 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.368 g, 0.635 mmol), and sodium tert-butoxide (2.14 g, 22.2 mmol) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M11-3 (4.98 g, 72% yield).

[0800]

[0801] (11-2) Synthesis of Intermediate M11-5 Under an argon atmosphere, a toluene (20 mL) solution of intermediate M11-3 (4.55 g, 10.4 mmol), intermediate M11-4 (1.50 g, 5.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.096 g, 0.104 mmol), 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene (0.121 g, 0.209 mmol), and sodium tert-butoxide (1.51 g, 15.7 mmol) was heated and stirred at 100°C for 6 hours. Toluene and water were added to the reaction solution, and the organic layer was separated. The mixture was then purified by column chromatography to obtain intermediate M11-5 (2.49 g, 48% yield).

[0802]

[0803] (11-3) Synthesis of Compound BD-11 Under an argon atmosphere, a tertiary butylbenzene (12 mL) solution of intermediate M11-5 (2.30 g, 2.31 mmol) was cooled to −78°C, and then a pentane solution of tertiary butyllithium (2.9 mL, 1.6 M, 4.71 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (2.31 g, 9.23 mmol) and diisopropylethylamine (0.597 g, 4.62 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After completion of the reaction, water and dichloromethane were added, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography and recrystallization to obtain Compound BD-11 (0.604 g, yield 27%). The molecular weight of compound BD-11 was 969, and the mass spectrum analysis result of the obtained compound showed m / z (mass-to-charge ratio) = 969, so that the compound was identified as compound BD-11.

[0804] 1... organic electroluminescence element, 10... organic layer, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer

Claims

1. A compound represented by the following general formula (1): (In the general formula (1), R １ ~R １１ 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 group represented by -Si(Rx)(Ry)(Rz), 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, with the proviso that R １ ~R ８ At least one of R is a substituted or unsubstituted carbazolyl group; １ ~R １１ Any pair of adjacent two or more of R １２ and R １３ are each independently a group represented by the following formula (12D), 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, with the proviso that R １２ and R １３ At least one of the groups is a group represented by the following general formula (12D): (In the general formula (12D), R ２１ ~R ２４ any one of R is a bonding position to a nitrogen atom in the general formula (1), and R is not a bonding position to a nitrogen atom in the general formula (1). ２１ ~R ２４ , and R ２５ ~R ２８ 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 group represented by -Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, and X is an oxygen atom, a sulfur atom, N(R ２９ ), or C(R ３０ ) (R ３１ ) and R ３０ and R ３１ are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, and R ２９ R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring; ３０ and R which does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. ３１ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ), a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ ) group represented by -O-(R １３６ ) group represented by -S-(R １３７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R １３８ A group represented by the formula: １３９ a halogen atom, a cyano group, a nitro group, -P(=O)(R １４０ ) (R １４１ a group represented by -Ge(R １４２ ) (R １４３ ) (R １４４ ), a group represented by -B(R １４５ ) (R １４６ 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.) (Rx, Ry, and Rz in the general formula (1), and Rx, Ry, Rz, and R in the general formula (12D) are each a group represented by the formula: １３１ ~R １４６ 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, when there are multiple Rx's, the multiple Rx's are the same or different from one another, when there are multiple Ry's, the multiple Ry's are the same or different from one another, when there are multiple Rz's, the multiple Rz's are the same or different from one another, R １３１ When there are multiple R １３１ are the same or different from each other, R １３２ When there are multiple R １３２ are the same or different from each other, R １３３ When there are multiple R １３３ are the same or different from each other, R １３４ When there are multiple R １３４ are the same or different from each other, R １３５ When there are multiple R １３５ are the same or different from each other, R １３６ When there are multiple R １３６ are the same or different from each other, R １３７ When there are multiple R １３７ are the same or different from each other, R １３８ When there are multiple R １３８ are the same or different from each other, R １３９ When there are multiple R １３９ are the same or different from each other, R １４０ When there are multiple R １４０ are the same or different from each other, R １４１ When there are multiple R １４１ are the same or different from each other, R １４２ When there are multiple R １４２ are the same or different from each other, R １４３ When there are multiple R １４３ are the same or different from each other, R １４４ When there are multiple R １４４ are the same or different from each other, R １４５ When there are multiple R １４５ are the same or different from each other, R １４６ When there are multiple R １４６ are the same or different from each other.) 2. R １ ~R ８ The compound according to claim 1 , wherein two of the groups are substituted or unsubstituted carbazolyl groups.

3. R １ ~R ４ one of which is a substituted or unsubstituted carbazolyl group, and R ５ ~R ８ The compound according to claim 1 or claim 2, wherein one of the following is a substituted or unsubstituted carbazolyl group:

4. R ２ and R ７ The compound according to any one of claims 1 to 3, wherein is a substituted or unsubstituted carbazolyl group.

5. R １ ~R ８ The compound according to any one of claims 1 to 4, wherein the substituted or unsubstituted carbazolyl group is a substituted or unsubstituted N-carbazolyl group.

6. The compound according to claim 5, wherein the compound represented by the general formula (1) is represented by the following general formula (11A): (In the above general formula (11A), R １ , R ３ ~R ６ , and R ８ ~R １３ are R in the general formula (1), １ , R ３ ~R ６ , and R ８ ~R １３ is synonymous with R ４１ , R ４２ , R ４３ , and R ４４ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ４５ , R ４６ , R ４７ , and R ４８ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ４９ , R ５０ , R ５１ , and R ５２ one or more pairs of adjacent two or more of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ５３ , R ５４ , R ５５ , and R ５６ one or more pairs of adjacent two or more of R 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, 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. ４１ ~R ５６ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R １３１ ) (R １３２ ), a group represented by —Si(R １３３ ) (R １３４ ) (R １３５ ) group represented by -O-(R １３６ ) group represented by -S-(R １３７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R １３８ A group represented by the formula: １３９ a halogen atom, a cyano group, a nitro group, -P(=O)(R １４０ ) (R １４１ a group represented by -Ge(R １４２ ) (R １４３ ) (R １４４ ), a group represented by -B(R １４５ ) (R １４６ 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, １３１ ~R １４６ are R in the general formula (12D), １３１ ~R １４６ (Same meaning as above.) 7. The compound according to any one of claims 1 to 6, wherein the group represented by the general formula (12D) is the following general formula (12D-1), (12D-2), or (12D-3): (In the general formulae (12D-1), (12D-2), and (12D-3), * represents the bonding position with the nitrogen atom in the general formula (1), and R ２１ ~R ２８ Each of them represents R in the general formula (12D). ２１ ~R ２８ (Same meaning as above.) 8. R ２１ is the bonding position to the nitrogen atom in the general formula (1), R ２２ is a hydrogen atom; R ２４ is the bonding position to the nitrogen atom in the general formula (1), R ２３ The compound according to any one of claims 1 to 7, wherein is a hydrogen atom.

9. R １２ and R １３ The compound according to any one of claims 1 to 8, wherein both of the following are groups represented by general formula (12D):

10. A compound according to any one of claims 1 to 9, wherein X is an oxygen atom.

11. R １ , R ３ , R ４ , R ５ , R ６ , R ８ , R ９ , and R １１ The compound according to any one of claims 1 to 10, wherein:

12. R １０ The compound according to any one of claims 1 to 11, wherein R is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

13. R ２１ is a hydrogen atom or a bonding position to the nitrogen atom in the general formula (1). The compound according to any one of claims 1 to 12.

14. R ２２ and R ２４ 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 bonding position with the nitrogen atom in general formula (1).

15. R ２３ is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

16. R in the general formula (12D-1) ２２ is a hydrogen atom, and R in the general formula (12D-2) ２１ and R ２３ is a hydrogen atom, and R in the general formula (12D-3) ２３ The compound according to claim 7 , wherein is a hydrogen atom.

17. R ２５ , R ２６ , R ２７ , and R ２８ The compound according to any one of claims 1 to 16, wherein:

18. The compound according to any one of claims 1 to 17, wherein the compound represented by the general formula (1) contains one or more deuterium atoms.

19. The compound according to any one of claims 1 to 18, wherein the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 13 ring atoms.

20. A compound according to any one of claims 1 to 18, wherein any group described as "substituted or unsubstituted" is an "unsubstituted" group.

21. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 20.

22. An organic electroluminescence element comprising a cathode, an anode, and an organic layer between the cathode and the anode, wherein at least one of the organic layers contains a compound according to any one of claims 1 to 20 as compound M3.

23. The organic electroluminescence device according to claim 22, wherein the organic layer includes an emitting layer, and the emitting layer contains the compound M3.

24. The organic electroluminescence device according to claim 23, wherein the light-emitting layer contains a sensitizing material, and the sensitizing material and the compound M3 are different compounds.

25. The organic electroluminescence device according to claim 24, wherein the sensitizing material is a delayed fluorescent compound.

26. The organic electroluminescence device according to claim 24 or 25, wherein the sensitizing material and the compound M3 are contained in a single layer.

27. The organic electroluminescence device according to any one of claims 23 to 26, wherein a hole transport layer is disposed between the anode and the light emitting layer.

28. The organic electroluminescence device according to any one of claims 23 to 27, wherein an electron transport layer is disposed between the cathode and the light-emitting layer.

29. An electronic device equipped with the organic electroluminescence element according to any one of claims 22 to 28.

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