Organic electroluminescent element and electronic device

Abstract

An organic electroluminescent element (1) has a negative electrode (4), a positive electrode (3), and a light-emitting layer (5) disposed between the negative electrode (4) and the positive electrode (3). The light-emitting layer (5) includes a compound M2 represented by general formula (1). The difference ΔST(M2) between the lowest excited singlet energy S1(M2) and the energy gap T77K(M2) at 77[K] of the compound M2 satisfies the relationship in the mathematical formula (formula 1).　Formula (1): ΔST(M2) = S1(M2) − T77K(M2) < 0.3eV. (In general formula (1): each of X1 to X4 independently is a nitrogen atom or CRx, provided that at least one of X1 to X4 is a nitrogen atom; and Ar1 is a hydrogen atom, a substituted or unsubstituted aryl group, or a group represented by general formula (2)).

Description

Organic electroluminescence element and electronic device

[0001] The present invention relates to an organic electroluminescence element 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 and 2). Examples of the performance of organic EL devices include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0003] US Patent Application Publication No. 2022 / 0177492 US Patent Application Publication No. 2021 / 0066613

[0004] An object of the present invention is to provide an organic electroluminescent element that emits light with high efficiency, and to provide an electronic device equipped with the organic electroluminescent element.

[0005] According to one aspect of the present invention, there is provided a light-emitting device comprising a cathode, an anode, and a light-emitting layer disposed between the cathode and the anode, wherein the light-emitting layer contains a compound M2 represented by the following general formula (1), and the lowest excited singlet energy S of the compound M2 is １ (M2) and the energy gap T at 77[K] ７７Ｋ The organic electroluminescence element is provided such that the difference ΔST(M2) between the first and second polarities satisfies the relationship of the following mathematical formula (1): ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV...(Math. 1)

[0006]

[0007]

[0008] (In the general formula (1), X １ ~X ４ are each independently a nitrogen atom or CRx, １ ~X ４ At least one of Rx's is a nitrogen atom, and when a plurality of Rx's are present, the plurality of Rx's are the same or different from one another; １ ~Y ３ are each independently a nitrogen atom or CH, provided that Y １ ~Y ３ two or more of the rings A, B, C, D and E are nitrogen atoms, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms, and Z １ ~Z ３ are each independently a single bond, C(R １ ) (R ２ ), N.R. ３ , an oxygen atom, or a sulfur atom; Z １ , Z ２ and Z ３ are the same or different from each other, Ar １ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), m is 1, 2, 3, 4 or 5, n is 0, 1, 2, 3 or 4, m+n=5, and when m is 2, 3, 4 or 5, a plurality of X １ are the same or different from each other, and a plurality of X ２ are the same or different from each other, and a plurality of X ３ are the same or different from each other, and a plurality of X ４ are the same or different from each other; multiple A rings are the same or different from each other; multiple Z １ are the same or different from each other, and when n is 2, 3 or 4, a plurality of Ar １are the same or different, *1 and *2 each represent a bonding position to a benzene ring, and in the general formula (2), Z is C(R １Ａ ) (R ２Ａ ), N.R. ３Ａ , an oxygen atom, or a sulfur atom; R １１ ~R １８ one or more pairs of adjacent two or more of Ar 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, with the proviso that Ar １ is a group represented by the general formula (2), R １１ ~R １８ and R ３Ａ one of Rx and R is a single bond to the benzene ring in the general formula (1); １ , R ２ , R ３ , R １Ａ , R ２Ａ and R which is not a single bond to the benzene ring, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ３Ａ and R １１ ~R １８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７are 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.)

[0009] 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.

[0010] According to one aspect of the present invention, there is provided a compound represented by the following general formula (100):

[0011]

[0012]

[0013] (In the general formula (100), Ar １００ is a group represented by the following general formula (1A), １００ When there are multiple Ar １００ are the same or different from each other, and Y １ ~Y ３ are each independently a nitrogen atom or CH, provided that Y１ ~Y ３ two or more of the rings B, C, D and E are nitrogen atoms, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms, and Z ２ and Z ３ are each independently a single bond, C(R １ ) (R ２ ), N.R. ３ , an oxygen atom, or a sulfur atom; Z ２ and Z ３ are the same or different from each other, Ar １ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), m is 1, 2, 3, 4 or 5, n is 0, 1, 2, 3 or 4, m+n=5, and when n is 2, 3 or 4, a plurality of Ar １ are the same or different, *1 and *2 each represent a bonding position to a benzene ring, and in the general formula (2), Z is C(R １Ａ ) (R ２Ａ ), N.R. ３Ａ , an oxygen atom, or a sulfur atom; R １１ ~R １８ one or more pairs of adjacent two or more of Ar 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, with the proviso that Ar １ is a group represented by the general formula (2), R １１ ~R １８ and R ３Ａ is a single bond to the benzene ring in the general formula (100), １ , R ２ , R ３ , R １Ａ , R ２Ａ and R which is not a single bond to the benzene ring, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ３Ａ , and R１１ ~R １８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 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, 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 R９０７ are the same or different from each other.)

[0014]

[0015] (In the general formula (1A), Z １ represents Z in the general formula (100). ２ and X １ ~X ４ are each independently a nitrogen atom or CRx, １ ~X ４ at least one of the rings is a nitrogen atom, the ring A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms, and Rx is R in the general formula (2). １１ ~R １８ When a plurality of A rings are present, the plurality of A rings are the same as or different from each other; When a plurality of Rx's are present, the plurality of Rx's are the same as or different from each other; When a plurality of groups represented by the general formula (1A) are present, the plurality of groups represented by the general formula (1A) are the same as or different from each other; *1 indicates the bonding position with the benzene ring in the general formula (100). １ ~Y ３ are nitrogen atoms, and in the general formula (100), at least one Ar １００ is a group represented by any one of the following general formulas (100A), (100B), (100C) and (100D), the general formula (100) satisfies at least one of the following requirements (i), (ii) and (iii): (i) at least one Ar １００ is a group represented by the following general formula (100A), m is 2, 3, 4 or 5, or n is 1, and one Ar １ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), or n is 2 and two Ar １ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a group represented by the general formula (2), or n is 3 and three Ar１ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), or n is 4 and four Ar １ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2). １００ is a group represented by the following general formula (100B), (100C) or (100D), at least one group represented by the following general formula (100B), (100C) or (100D) is bonded to the carbon atom at the position a in the general formula (100). １００ is a group represented by the following general formula (100B), (100C), or (100D), ring B, ring C, ring D, and ring E are each independently an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocycle having 5 to 60 ring atoms.

[0016]

[0017] (In the general formulae (100A), (100B), (100C) and (100D), R ３１１ ~R ３１４ 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 to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring ３１１ ~R ３１４ are each independently R in the general formula (2). １１ ~R １８wherein ring A is the same as ring A in general formula (1A); when a plurality of rings A are present, the plurality of rings A are the same as or different from one another; when a plurality of groups represented by general formula (100A) are present, the plurality of groups represented by general formula (100A) are the same as or different from one another; when a plurality of groups represented by general formula (100B) are present, the plurality of groups represented by general formula (100B) are the same as or different from one another; when a plurality of groups represented by general formula (100C) are present, the plurality of groups represented by general formula (100C) are the same as or different from one another; when a plurality of groups represented by general formula (100D) are present, the plurality of groups represented by general formula (100D) are the same as or different from one another; *1 indicates the bonding position to the benzene ring in general formula (100).

[0018] According to one embodiment of the present invention, it is possible to provide an organic electroluminescence element that emits light with high efficiency, and to provide an electronic device equipped with the organic electroluminescence element.

[0019] Fig. 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a first 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 emitting layer of an example of an organic electroluminescence element according to a first embodiment of the present invention, as well as the relationship between energy transfer; Fig. 5 is a diagram showing the energy levels of a second host material, a sensitizing material, and a fluorescent material in an emitting layer of an example of an organic electroluminescence element according to a second embodiment of the present invention, as well as the relationship between energy transfer.

[0020] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0028] 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.

[0029] "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.

[0030] 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).

[0031]

[0032]

[0033] 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.

[0034] "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.

[0035] 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).

[0036] 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).

[0037] 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.

[0038] 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.

[0039] 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).

[0040] 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):

[0041]

[0042]

[0043] 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:

[0044] 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.

[0045] 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].

[0046] 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].

[0047] 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):

[0048] 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).

[0049] "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.

[0050] 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.

[0051] 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.

[0052] "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.

[0053] 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.

[0054] 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.

[0055] - "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.

[0056] Unsubstituted alkynyl groups (specific example group G5A): ethynyl groups.

[0057] "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.

[0058] 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.

[0059] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0060] -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.

[0061] ・「-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.

[0062] ・"-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.

[0063] ・「-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.

[0064] "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.

[0065] "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.

[0066] "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.

[0067] - "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.

[0068] - "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.

[0069] - "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.

[0070] - "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.

[0071] - "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.

[0072] "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.

[0073] 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.

[0074] 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.

[0075] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0076]

[0077] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0078]

[0079] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0080] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0081]

[0082] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0083] 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.

[0084] "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.

[0085] "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.

[0086] "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.

[0087] 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).

[0088]

[0089]

[0090] 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.

[0091]

[0092] 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.

[0093]

[0094] 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.

[0095] 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).

[0096]

[0097]

[0098]

[0099] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0100]

[0101]

[0102]

[0103]

[0104] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0105] The above is the explanation of "substituents described in this specification."

[0106] "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.

[0107]

[0108] 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.

[0109] 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).

[0110]

[0111] 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.

[0112]

[0113] 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.

[0114] 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

[0115] 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.

[0116] 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").

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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."

[0121] 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.

[0122] 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.

[0123] 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.

[0124] First Embodiment (Organic Electroluminescence Element) An organic EL element according to this embodiment will be described. The organic EL element according to this embodiment includes an organic layer between an anode and a cathode. This organic layer includes at least one layer made of an organic compound. Alternatively, this organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic compound.

[0125] The organic EL device according to this embodiment includes a cathode, an anode, and an emitting layer disposed between the cathode and the anode. The emitting layer contains a compound M2 represented by the following general formula (1), and the lowest excited singlet energy S of the compound M2 is １ (M2) and the energy gap T at 77[K] ７７Ｋ The difference ΔST(M2) between the first and second sine waves (M2) satisfies the relationship of the following formula (Formula 1): ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV...(Math. 1)

[0126] In this embodiment, compound M2 contained in the light-emitting layer has a structure in which at least (i) an azine ring having two donor groups such as carbazolyl groups, and (ii) a donor group including a nitrogen-containing six-membered ring structure such as an azacarbazolyl group are bonded to a benzene ring. Compound M2 has the above (i) and (ii), thereby achieving the following effects. In compound M2, the azacarbazolyl group as a donor group including a nitrogen-containing six-membered ring structure has weaker electron-donating properties than a carbazolyl group not including a nitrogen-containing six-membered ring structure, but is a moiety with a higher minimum excited triplet energy. Therefore, by using compound M2, it is possible to achieve a maximum peak wavelength λ of fluorescent emission while maintaining TADF properties. ＦＬ In addition, by using the compound M2, the maximum fluorescence emission peak wavelength λ ＦＬ Since the wavelength of light is shortened, blue chromaticity is improved. As a result, it is possible to provide an organic electroluminescence element having an improved BI (Blue Index), which is an index of luminous efficiency that also takes chromaticity into account. In this specification, the value of "L / J / CIEy" is referred to as the Blue Index (BI). The chromaticity CIEy and current efficiency L / J (unit: cd / A) are calculated by the method described in the Examples.

[0127] For example, the following compound TADF-A has a structure in which an azine ring having one donor group (carbazolyl group) and a donor group (azacarbazolyl group) containing a nitrogen-containing six-membered ring structure are bonded to a benzene ring. The following compound TADF-B is a compound in which the azacarbazolyl group in compound TADF-A is replaced with a carbazolyl group. As shown below, compound TADF-A has a maximum fluorescence emission peak wavelength λ 2 , which is longer than that of compound TADF-B. ＦＬ The maximum peak wavelength of fluorescence λ ＦＬ is measured by the method described in the Examples.

[0128]

[0129] (Organic Layer) In the organic EL device of this embodiment, the organic layer may be composed of, for example, a single light-emitting layer, or may include layers that can be used in an organic EL device. Layers that can be used in an organic EL device are not particularly limited, and examples 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. In one aspect of the organic EL device of this embodiment, the light-emitting layer contains compound M2 (a compound represented by general formula (1)) as a host material. In this case, the host material is preferably a delayed fluorescent compound. In this specification, compound M2 used as the host material may be referred to as a first host material. In one aspect of the organic EL device of this embodiment, the light-emitting layer includes an anode, a cathode, and an light-emitting layer disposed between the anode and the cathode. The light-emitting layer contains a first host material (preferably a sensitizing material) and a fluorescent material, and the first host material is compound M2. The first host material and the fluorescent material are different compounds. In one embodiment, the light-emitting layer does not contain a metal complex. In one embodiment, the light-emitting layer does not contain a phosphorescent material.

[0130] In the organic EL element of this embodiment, a hole transport layer may be disposed between the anode and the light-emitting layer.

[0131] In the organic EL element of this embodiment, an electron transport layer may be disposed between the cathode and the light-emitting layer.

[0132] 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.

[0133] (Emitting Layer) In one embodiment, the first host material (compound M2) and the fluorescent material are contained in a single layer. For example, when the organic EL device has one emitting layer, the first host material and the fluorescent material are contained in the single emitting layer. When the organic EL device has multiple emitting layers, the first host material and the fluorescent material are contained in any one of the multiple emitting layers.

[0134] [First Host Material (Compound M2)] In one embodiment, the first host material (compound M2) is a sensitizing material. In one embodiment, the emitting layer contains compound M2 as the sensitizing material. In one embodiment, the sensitizing material is a delayed fluorescent compound. In one embodiment, the emitting layer contains a sensitizing material as compound M2 and a fluorescent material. In one embodiment, when the emitting layer contains a delayed fluorescent compound as the sensitizing material, the emitting layer does not contain a phosphorescent metal complex.

[0135] In this embodiment, the first host material is a compound M2 represented by the following general formula (1).

[0136]

[0137]

[0138] (In the general formula (1), X １ ~X ４ are each independently a nitrogen atom or CRx, １ ~X ４ At least one of Rx's is a nitrogen atom, and when a plurality of Rx's are present, the plurality of Rx's are the same or different from one another; １ ~Y ３ are each independently a nitrogen atom or CH, provided that Y １ ~Y ３ two or more of the rings A, B, C, D and E are nitrogen atoms, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms, and Z １ ~Z ３are each independently a single bond, C(R １ ) (R ２ ), N.R. ３ , an oxygen atom, or a sulfur atom; Z １ , Z ２ and Z ３ are the same or different from each other, Ar １ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), m is 1, 2, 3, 4 or 5, n is 0, 1, 2, 3 or 4, m+n=5, and when m is 2, 3, 4 or 5, a plurality of X １ are the same or different from each other, and a plurality of X ２ are the same or different from each other, and a plurality of X ３ are the same or different from each other, and a plurality of X ４ are the same or different from each other; multiple A rings are the same or different from each other; multiple Z １ are the same or different from each other, and when n is 2, 3 or 4, a plurality of Ar １ are the same or different, *1 and *2 each represent a bonding position to a benzene ring, and in the general formula (2), Z is C(R １Ａ ) (R ２Ａ ), N.R. ３Ａ , an oxygen atom, or a sulfur atom; R １１ ~R １８ one or more pairs of adjacent two or more of Ar 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, with the proviso that Ar １ is a group represented by the general formula (2), R １１ ~R １８ and R ３Ａ one of Rx and R is a single bond to the benzene ring in the general formula (1); １ , R ２ , R ３ , R １Ａ , R ２Ａand R which is not a single bond to the benzene ring, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ３Ａ and R １１ ~R １８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 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, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other.)

[0139] In the compound M2 of this embodiment, Z １ , Z ２ and Z ３ is preferably a single bond.

[0140] In compound M2 of this embodiment, it is preferable that ring A, ring B, ring C, ring D, and ring E are each independently a substituted or unsubstituted benzene ring, or a substituted or unsubstituted dibenzothiophene ring. In compound M2 of this embodiment, it is preferable that ring B and ring C are both substituted or unsubstituted benzene rings, or that one of ring B and ring C is a substituted or unsubstituted benzene ring and the other is a substituted or unsubstituted dibenzothiophene ring. In compound M2 of this embodiment, it is preferable that ring D and ring E are both substituted or unsubstituted benzene rings, or that one of ring D and ring E is a substituted or unsubstituted benzene ring and the other is a substituted or unsubstituted dibenzothiophene ring.

[0141] In the compound M2 of this embodiment, X １ ~X ３ is a nitrogen atom, and X is not a nitrogen atom １ ~X ４ is preferably CRx.

[0142] In the compound M2 of this embodiment, X ２ or X ４ is a nitrogen atom, and X is not a nitrogen atom １ ~X ４ In one embodiment of the compound M2, X is preferably CRx. １ is a nitrogen atom, and X ２ ~X ４ In one embodiment of the compound M2, X ２ is a nitrogen atom, and X １ , X ３ and X ４In one embodiment of the compound M2, X ３ is a nitrogen atom, and X １ , X ２ and X ４ In one embodiment of the compound M2, X ４ is a nitrogen atom, and X １ , X ２ and X ３ is CRx.

[0143] In the compound M2 of this embodiment, Y ２ and Y ３ are nitrogen atoms, and Y １ is CH, or Y １ ~Y ３ In the compound M2 of this embodiment, it is preferable that three of Y １ ~Y ３ It is more preferable that three of the above are nitrogen atoms.

[0144] In the compound M2 of this embodiment, Ar １ is preferably a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0145] In the compound M2 of this embodiment, it is preferable that the partial structures represented by the following general formula (1A) in the compound M2 are each independently a group represented by any one of the following general formulas (11A) to (14A). When the compound M2 has a plurality of partial structures represented by the following general formula (1A), the plurality of partial structures represented by the following general formula (1A) are the same as or different from each other.

[0146]

[0147] (In the general formula (1A), ring A, X １ ~X ４ and Z １ respectively represent the ring A and X in the general formula (1). １ ~X ４ and Z １When a plurality of partial structures represented by the general formula (1A) are present, the plurality of partial structures represented by the general formula (1A) are the same as or different from one another, and *1 has the same meaning as *1 in the general formula (1).

[0148]

[0149] (In the general formulae (11A) to (14A), R ３１１ ~R ３１８ 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 to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring ３１１ ~R ３１８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R in the general formulae (11A) to (14A) is a group represented by the formula (11A) to (14A). ９０１ ~R ９０７ are R in the general formula (1), respectively. ９０１ ~R ９０７ *1 has the same meaning as *1 in the general formula (1A).

[0150] In the general formulae (11A) to (14A), R ３１１ ~R ３１８It is preferable that any pair of two or more adjacent groups among the above do not bond to each other.

[0151] In the compound M2 of the present embodiment, it is also preferable that the partial structures represented by the general formula (1A) in the compound M2 are each independently a group represented by any one of the following general formulas (15A) to (18A):

[0152]

[0153] (In the general formulae (15A) to (18A), A １ The ring is a ring structure represented by the following general formula (19A): ２ The ring is a ring structure represented by the following general formula (20A): １ Ring and A ２ The ring is fused to the adjacent ring at any position, and R ３１１ ~R ３１４ 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, ４１１ ~R ４１４ at least one pair 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 in the general formulae (15A) to (18A), R do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ３１１ ~R ３１４ and R ４１１ ~R ４１４ each independently represents R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring in the general formulae (11A) to (14A). ３１１ ~R ３１８ *1 has the same meaning as *1 in the general formula (1A).

[0154]

[0155] (In the general formula (19A), a plurality of R４１５ 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 to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring ４１５ is R in the general formulae (11A) to (14A) which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３１１ ~R ３１８ and plural R ４１５ are the same or different from each other, and in the general formula (20A), Z １２ is C(R １Ｂ ) (R ２Ｂ ), N.R. ３Ｂ , an oxygen atom, or a sulfur atom; R １Ｂ , R ２Ｂ and R ３Ｂ each independently represents R in the general formulae (11A) to (14A) which does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. ３１１ ~R ３１８ is synonymous with

[0156] In the general formulae (15A) to (18A), R ３１１ ~R ３１４ and R ４１１ ~R ４１４ In the general formula (19A), it is preferable that any pair of adjacent two or more R ４１５ In the general formulae (19A) and (20A), it is preferable that the groups consisting of R ４１５ , R １Ｂ , R ２Ｂ and R ３Ｂ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. １２ is preferably a sulfur atom.

[0157] In the compound M2 of this embodiment, it is preferable that the partial structure represented by the following general formula (1B) and the partial structure represented by the following general formula (1C) in the compound M2 are each independently a group represented by any one of the following general formulas (11B) to (13B). The partial structure represented by the following general formula (1B) and the partial structure represented by the following general formula (1C) are the same as or different from each other.

[0158]

[0159] (In the general formulae (1B) and (1C), ring B, ring C, ring D, ring E, Z ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (1). ２ and Z ３ *3 is the same as the Y １ and Y ３ *4 indicates the bonding position to the carbon atom between the Y ２ and Y ３ This indicates the bond position to the carbon atom between

[0160]

[0161] (In the general formulae (11B) to (13B), R ５１１ ~R ５１４ and R ５２０ 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, ６１１ ~R ６１４ and R ６２０ At least one pair of adjacent two or more R are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and a plurality of R ５２０ are the same or different from each other, and a plurality of R ６２０ are the same or different from each other, Ar ３is 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 does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. ５１１ ~R ５１４ , R ５２０ , R ６１１ ~R ６１４ and R ６２０ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R in the general formulae (11B) to (13B) is ９０１ ~R ９０７ are R in the general formula (1), respectively. ９０１ ~R ９０７ *5 has the same meaning as *3 in the general formula (1B) or *4 in the general formula (1C).

[0162] In the general formulae (11B) to (13B), R ５１１ ~R ５１４ , R ５２０ , R ６１１ ~R ６１４ and R ６２０ It is preferable that any pair of two or more adjacent groups among the above do not bond to each other.

[0163] In the present embodiment, in the compound M2, it is also preferable that the partial structure represented by the general formula (1B) and the partial structure represented by the general formula (1C) are each independently a group represented by the following general formula (14B) or (15B):

[0164]

[0165] (In the general formula (14B), Z １３ is C(R １Ｃ ) (R ２Ｃ ), an oxygen atom, or a sulfur atom; R １Ｃ and R ２Ｃ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ５１１ ~R ５１４ , R ５２０ , R ６１１ ~R ６１４ and R ６２０ are R in the general formula (13B), respectively. ５１１ ~R ５１４ , R ５２０ , R ６１１ ~R ６１４ and R ６２０ *5 has the same meaning as *3 in the general formula (1B) or *4 in the general formula (1C). １ Tamaki, B ２ Ring, R ３１１Ｂ ~R ３１４Ｂ and R ４１１Ｂ ~R ４１４Ｂ are A in the general formulae (15A) to (18A), respectively. １ Tamaki, A ２ Ring, R ３１１ ~R ３１４ and R ４１１ ~R ４１４ *5 has the same meaning as *3 in the general formula (1B) or *4 in the general formula (1C).

[0166] In the general formula (14B), R ５１１ ~R ５１４ , R５２０ , R ６１１ ~R ６１４ and R ６２０ In the general formula (15B), it is preferable that any pair of adjacent two or more groups of R ３１１Ｂ ~R ３１４Ｂ and R ４１１Ｂ ~R ４１４Ｂ In the general formula (15B), it is preferable that any pair of two or more adjacent groups of B ２ In the general formula (20A) representing a ring, Z １２ is preferably a sulfur atom.

[0167] In one embodiment, m is 1, 2, 3 or 4. In one embodiment, m is 1, 2 or 3. In one embodiment, m is 1 or 2. In one embodiment, m is 1.

[0168] In this embodiment, the compound M2 is preferably a compound represented by any one of the following general formulas (110) to (117).

[0169]

[0170]

[0171]

[0172]

[0173] (In the general formulae (110) to (113), R ３１１ ~R ３１８ respectively represent R in the general formulae (11A) to (14A). ３１１ ~R ３１８ is synonymous with Y １ ~Y ３ , Ar １ , m and n are the same as Y in the general formula (1), respectively. １ ~Y ３ , Ar １ , m and n are defined the same as *1 and *2 in the general formula (1), respectively; R ５１１ ~R ５１４ and R ５２０are R in the general formula (11B), respectively. ５１１ ~R ５１４ and R ５２０ is synonymous with R ５１１Ａ ~R ５１４Ａ and R ５２０Ａ are R in the general formula (11B), respectively. ５１１ ~R ５１４ and R ５２０ and plural R ５２０Ａ are the same or different.)

[0174]

[0175]

[0176]

[0177]

[0178] (In the general formulae (114) to (117), A １ Tamaki, A ２ Ring, R ３１１ ~R ３１４ and R ４１１ ~R ４１４ respectively represent A in the general formulae (15A) to (18A). １ Tamaki, A ２ Ring, R ３１１ ~R ３１４ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ , Ar １ , m and n are the same as Y in the general formula (1), respectively. １ ~Y ３ , Ar １ , m and n are defined the same as *1 and *2 in the general formula (1), respectively; R ５１１ ~R ５１４ and R ５２０ are R in the general formula (11B), respectively. ５１１ ~R ５１４ and R ５２０ is synonymous with R ５１１Ａ ~R ５１４Ａ and R ５２０Ａare R in the general formula (11B), respectively. ５１１ ~R ５１４ and R ５２０ and plural R ５２０Ａ are the same or different.)

[0179] In the general formulae (110) to (117), R ５１１ ~R ５１４ and R ５２０ and R ５１１Ａ ~R ５１４Ａ and R ５２０Ａ In the general formulae (110) to (117), it is preferable that any pair of adjacent two or more R ５１１ ~R ５１４ and R ５２０ Any pair of two or more adjacent groups of R ５１１Ａ ~R ５１４Ａ and R ５２０Ａ It is also preferred that one or more pairs of adjacent two or more of the above groups are bonded to each other to form a substituted or unsubstituted monocycle, or to form a substituted or unsubstituted fused ring.

[0180] In the compound M2 of this embodiment, Rx, R １ , R ２ , R ３ , R １Ａ , R ２Ａ , R ３Ａ and R １１ ~R １８ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ３１１ ~R ３１８ , R ４１１ ~R ４１４ , R ４１５ , R ５１１ ~R ５１４ , R ５２０ , R ６１１ ~R ６１４ , R ６２０ , R３１１Ｂ ~R ３１４Ｂ , R ４１１Ｂ ~R ４１４Ｂ , R ５１１Ａ ~R ５１４Ａ and R ５２０Ａ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0181] In one embodiment, compound M2 comprises at least one deuterium atom. In one embodiment, compound M2 comprises no deuterium atoms.

[0182] In the compound M2 of this embodiment, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ and R ９０７ 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.

[0183] In compound M2 of 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. In compound M2 of this embodiment, the substituent in the case of "substituted or unsubstituted" is more 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. In compound M2 of this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0184] (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.

[0185] In general, delayed fluorescence can be confirmed by transient PL (Photoluminescence) measurement.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] 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.

[0190] 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.

[0191] 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.

[0192]

[0193] 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.

[0194] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0195]

[0196] 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.

[0197] 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.

[0198] 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.

[0199] 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.

[0200] 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.

[0201] (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.

[0202] In this embodiment, the lowest excited singlet energy S of the compound M2 (preferably a delayed fluorescent compound) １ (M2) and the energy gap T of compound M2 at 77 [K] ７７Ｋ The difference ΔST(M2) between the lowest excited singlet energy S of the compound M2 (preferably a delayed fluorescent compound) and the lowest excited singlet energy S of the compound M2 (preferably a delayed fluorescent compound) is less than 0.3 eV, preferably less than 0.2 eV, more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. １ (M2) and the energy gap T at 77[K] ７７Ｋ The difference ΔST(M2) between (M2) satisfies the relationship of the following mathematical formula (Math. 1). It is preferable that the ΔST(M2) satisfies the relationship of the following mathematical formula (Math. 1A), (Math. 1B), or (Math. 1C). ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV...(Math. 1) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.2eV...(Math. 1A) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.1eV...(Math. 1B) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.01eV...(Math. 1C)

[0203] (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

[0204] 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.

[0205] (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 manufactured by Hitachi (device name: U3310), but is not limited to this.

[0206] 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.

[0207] (Method for Producing Compound M2) Compound M2 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.

[0208] (Specific Examples of Compound M2) Specific examples of compound M2 according to this embodiment include the following compounds: However, the present invention is not limited to these specific examples.

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] [Fluorescent Material] In one aspect of this embodiment, the fluorescent material is a compound that does not exhibit thermally activated delayed fluorescence. In one aspect of this embodiment, the fluorescent material is a compound that exhibits thermally activated delayed fluorescence. In one aspect of this embodiment, the fluorescent material is not a phosphorescent metal complex. In one aspect of this embodiment, it is preferable that the fluorescent material is not a metal complex. In this specification, a compound used as a fluorescent material may be referred to as compound M3.

[0234] In the third embodiment, examples of the compound M3 (fluorescent material) include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing a boron atom, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0235] In this embodiment, the fluorescent material (compound M3) is preferably a compound represented by the following general formula (41).

[0236]

[0237] (In the general formula (41), the ring a, the ring b, and the ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, and L ４０１ and L ４０２ are each independently O, S, Se, or NR ４０ , C(R ４１ ) (R ４２ ), or Si(R ４３ ) (R ４４ ) and L ４０３ is B, P, or P=O, and R ４０ ~R ４４ each independently represents a ring a, a ring b, or a ring c bonded to form a substituted or unsubstituted monocycle, a ring a, a ring b, or a ring c bonded to form a substituted or unsubstituted fused ring, or a ring a, a ring b, or a ring c is not bonded to any of the rings a, b, and c, and R ４１ and R ４２are 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 ４３ and R ４４ 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 do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０ ~R ４４ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N, 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, ４５ is a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R ４０ If there are multiple R ４０ are the same or different from each other, R ４１ If there are multiple R ４１ are the same or different from each other, R ４２ If there are multiple R ４２ are the same or different from each other, R ４３ If there are multiple R ４３ are the same or different from each other, R ４４ If there are multiple R ４４ are the same or different from each other, R ４５ If there are multiple R ４５ are the same or different from each other.)

[0238] In this embodiment, the compound represented by the general formula (41) is preferably a compound represented by the following general formula (410).

[0239]

[0240] (In the general formula (410), the ring a, the ring b, and the ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, and R ４０１ and R ４０２ each independently represents R which bonds with the ring a, ring b, or ring c to form a substituted or unsubstituted monocycle, R which bonds with the ring a, ring b, or ring c to form a substituted or unsubstituted fused ring, or R which does not bond with the ring a, ring b, or ring c to form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N; 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.

[0241] In this embodiment, the compound represented by the general formula (41) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (41-1) to (41-6).

[0242]

[0243]

[0244]

[0245] (In the general formula (41-1), Xa is O, S, Se, C(R ４０３ ) (R ４０４), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ a set of two or more adjacent ４２７ and R ４１２ and R ４１２ and R ４１１ and R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N, 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１１ , R ４１２ , and R ４２１ ~R ４２７ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘeach independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, 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, 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.) (In the general formula (41-2), Xa is O, S, Se, C(R４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ a set of two or more adjacent ４１３ and R ４１４ and R ４１４ and R ４０１ and R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N, 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１３ , R ４１４ , and R ４２１ ~R ４２７ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ (In the general formula (41-3), Xa and Xb each independently represent O, S, Se, C(R ４０３ ) (R４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４１５ and R ４１６ Paired with R ４１６ and R ４１２ and R ４１２ and R ４１１ and R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N, 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１１ , R ４１２ , R ４１５ , R ４１６ , and R ４２１ ~R ４２３ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with R ４０３ If there are multiple R ４０３ are the same or different from each other, R ４０４ If there are multiple R４０４ are the same or different from each other, R ４０５ If there are multiple R ４０５ are the same or different.) (In the general formula (41-4), Xa and Xb each independently represent O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４１８ Paired with R ４１８ and R ４１７ and R ４１２ and R ４１１ and R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N, 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, ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１１ , R ４１２ , R ４１７ , R ４１８ , and R ４２１ ~R ４２３ are each independently a hydrogen atom or a substituent R Ｘand the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with R ４０３ If there are multiple R ４０３ are the same or different from each other, R ４０４ If there are multiple R ４０４ are the same or different from each other, R ４０５ If there are multiple R ４０５ are the same or different.) (In the general formula (41-5), Xa and Xb each independently represent O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４１８ Paired with R ４１８ and R ４１７ Paired with R ４１３ and R ４１４ and R ４１４ and R ４０１ and R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０１ and R ４０２ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -CR ４５ an iminyl group represented by ═N, 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, ４０３ ~R４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４１３ , R ４１４ , R ４１７ , R ４１８ , and R ４２１ ~R ４２３ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with R ４０３ If there are multiple R ４０３ are the same or different from each other, R ４０４ If there are multiple R ４０４ are the same or different from each other, R ４０５ If there are multiple R ４０５ are the same or different.) (In the general formula (41-6), R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３ and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ a set of two or more adjacent ４２７ and R ４２８ Paired with R ４２８ ~R ４３１ and R ４３１ and R ４０１ and R are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, and do not form the substituted or unsubstituted monocycle or the substituted or unsubstituted fused ring. ４０１ and R ４０２each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by ═N, 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, wherein R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring; ４２１ ~R ４３１ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with

[0246] In the compounds represented by the general formulas (41-1) to (41-5), R ４１２ and R ４１１ Paired with R ４１３ and R ４１４ Paired with R ４１５ and R ４１６ and R ４１７ and R ４１８ and

[0247] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (41-7).

[0248]

[0249] (In the general formula (41-7), Xa is O, S, Se, C(R ４０３ ) (R ４０４ ), or NR ４０５ and R ４０１ and R ４２１ Paired with R ４２１ ~R ４２３ a set of two or more adjacent ４２３and R ４０２ Paired with R ４０２ and R ４２４ Paired with R ４２４ ~R ４２７ and R ４３７ ~R ４４０ 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 to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring. ４０１ and R ４０２ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ４０３ ~R ４０５ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ４２１ ~R ４２７ and R ４３７ ~R ４４０ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with

[0250] In this embodiment, R ４０１ and R ４０２ are each independently 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, more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and even more preferably a group represented by the following general formula (42):

[0251]

[0252] (In the general formula (42), R ４３２ ~R ４３６ 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 to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring ４３２ ~R ４３６ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ and plural R ４３２ If there are multiple R ４３２ are the same or different from each other, and a plurality of R ４３３ If there are multiple R ４３３ are the same or different from each other, and a plurality of R ４３４ If there are multiple R ４３４ are the same or different from each other, and a plurality of R ４３５ If there are multiple R ４３５ are the same or different from each other, and a plurality of R ４３６ If there are multiple R ４３６ are the same or different, and * indicates the bonding position.)

[0253] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-1).

[0254] (In the general formula (42-1), R ４２１ ~R ４３１ are R in the general formula (41-6), respectively. ４２１ ~R ４３１ is synonymous with R ４５１ ~R ４５５one 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, ４５６ ~R ４６０ 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 to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring ４５１ ~R ４５５ and R ４５６ ~R ４６０ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with

[0255] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-2).

[0256]

[0257] (In the general formula (42-2), R ４２２ , R ４２６ , R ４２９ , R ４５３ , and R ４５８ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with

[0258] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-3).

[0259]

[0260] (In the general formula (42-3), R ４２１ ~R ４２７ , R ４３７ ~R ４４０and Xa are each R in the general formula (41-7). ４２１ ~R ４２７ , R ４３７ ~R ４４０ and Xa; R ４５１ ~R ４５５ 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, ４５６ ~R ４６０ 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 to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring ４５１ ~R ４５５ and R ４５６ ~R ４６０ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with

[0261] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-4).

[0262]

[0263] (In the general formula (42-4), Xa has the same meaning as Xa in the general formula (41-7), and R ４２２ , R ４２６ , R ４２９ , R ４３９ , R ４５３ , and R ４５８ are each independently a hydrogen atom or a substituent R Ｘ and the substituent R Ｘ represents the substituent R in the general formula (41-1). Ｘ is synonymous with

[0264] In this embodiment, R in compound M3 ４２２ , R４２６ , R ４２９ , R ４３９ , R ４５３ , and R ４５８ are each independently preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0265] In this embodiment, it is preferred that Xa and Xb in compound M3 each independently represent O or S.

[0266] (Method for producing a compound represented by general formula (41)) The compound represented by general formula (41) can be produced by a known method. The compound represented by general formula (41) can also be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0267] (Specific Examples of Compounds Represented by General Formula (41)) Specific examples of the compounds represented by the general formula (41) include the following compounds: In the specific examples below, Me represents a methyl group, tBu represents a tertiary butyl group, and Ph represents a phenyl group.

[0268]

[0269]

[0270]

[0271]

[0272] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the general formulae is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ａ ) (R ９０２ａ ) (R ９０３ａ ), -O-(R ９０４ａ ), -S-(R ９０５ａ ), -N(R ９０６ａ ) (R ９０７ａ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ａ ~R ９０７ａ are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ａ When two or more R ９０１ａ are the same or different, R ９０２ａ When two or more R ９０２ａ are the same or different, R ９０３ａ When two or more R ９０３ａ are the same or different, R ９０４ａ When two or more R ９０４ａ are the same or different, R ９０５ａ When two or more R ９０５ａ are the same or different, R ９０６ａ When two or more R ９０６ａ are the same or different, R ９０７ａ When two or more R ９０７ａ are the same as or different from each other.

[0273] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the general formulas is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0274] In one embodiment, the substituent in the case of "substituted or unsubstituted" in each of the general formulas is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0275] (Maximum Peak Wavelength) In this embodiment, the maximum peak wavelength of the compound M3 as a fluorescent material is preferably 480 nm or less, more preferably 475 nm or less. In this embodiment, the maximum peak wavelength of the 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 is referred to as the maximum peak wavelength λ of fluorescent emission. ＦＬ In the organic EL device of this embodiment, the first compound preferably emits blue light. In this specification, blue light emission refers to light emission having a maximum peak wavelength in the fluorescence spectrum of 430 nm or more and 480 nm or less.

[0276] (Emission spectrum half width) In this embodiment, the emission spectrum half width FWHM of the compound M3 as a fluorescent material is preferably 40 nm or less, more preferably 30 nm or less. In this embodiment, the emission spectrum half width FWHM of the compound M3 as a fluorescent material is preferably 5 nm or more, more preferably 10 nm or more. FWHM is an abbreviation for full width at half maximum.

[0277] In this specification, the maximum fluorescence emission peak wavelength λ ＦＬ The compound to be measured is 10 －６ moles / liter or more, 10 －５ For a toluene solution in which the compound is dissolved at a concentration of 1 mole / liter or less, the maximum peak wavelength λ of the fluorescence spectrum at which the emission intensity is maximized in the measured fluorescence spectrum is ＦＬ The emission spectrum half width FWHM is the full width at half maximum at the maximum peak of the fluorescence spectrum. A fluorescence spectrum measuring device can be used as a device for measuring the fluorescence spectrum. For example, a fluorescence spectrum measuring device (device name: FP-8300) manufactured by JASCO Corporation can be used. Note that the fluorescence spectrum measuring device is not limited to the device exemplified here.

[0278] (Stokes Shift) In this embodiment, the Stokes shift of compound M3 as a fluorescent material is preferably 25 nm or less, more preferably 20 nm or less. In this embodiment, the Stokes shift of compound M3 as a fluorescent material is preferably 5 nm or more, more preferably 10 nm or more. When the Stokes shift of compound M3 is 20 nm or less, excitation energy can be reduced. When the Stokes shift of compound M3 is 10 nm or more, self-absorption can be suppressed and loss of efficiency can be reduced. The Stokes shift can be measured by the following method. The compound to be measured is added to 2.0 × 10 －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.

[0279] (Relationship between Sensitizer Material and Fluorescent Material in Emitting Layer) In one embodiment, the sensitizer material (compound M2) as the first host material is a delayed fluorescent compound. In one embodiment, when the emitting layer contains a delayed fluorescent compound as the sensitizer material, the emitting layer does not contain a phosphorescent metal complex.

[0280] 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 (compound M2) as a sensitizing material and a fluorescent material (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.

[0281] In one embodiment, when compound M2 is a sensitizer, the lowest excited singlet energy S １ (GT2) and the lowest excited singlet energy S of the fluorescent material １ It is preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 3): S １ (GT2)>S １ (D) ... (Equation 3)

[0282] In one embodiment, when the compound M2 is a sensitizing material, the energy gap T ７７Ｋ (GT2) and the energy gap T of the fluorescent material at 77 [K] ７７Ｋ It is also preferable that (D) satisfies the relationship of the following mathematical formula (Mathematical Formula 6A): T ７７Ｋ (GT2)>T７７Ｋ (D) ... (Math 6A)

[0283] When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound in the light-emitting layer mainly emits light.

[0284] 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).

[0285] (Content of Compounds in Emitting Layer) The contents of the first host material (compound M2) and the fluorescent material (compound M3) contained in the 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 emitting layer contains materials other than compound M2 and compound M3. The 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.

[0286] The structure of the organic EL element will be further described.

[0287] (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.

[0288] (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, graphene, etc. 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).

[0289] 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.

[0290] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, and therefore materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0291] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used, including alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering can be used. Furthermore, when using silver paste or the like, coating or inkjet printing can be used.

[0292] 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.

[0293] 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.

[0294] (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), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0295] 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.

[0296] By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0297] 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.

[0298] 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.

[0299] 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.

[0300] (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.

[0301] (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, or manganese oxide. Furthermore, examples of the material 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, Examples of the aromatic amine compound include 3,5-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, a polymer compound (such as an oligomer, dendrimer, or polymer) can also be used as the substance with high hole injection properties. 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.

[0302] (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 (abbreviation: NPB), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 －６ cm ２ The 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.

[0303] (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, ZnBTZ, and other metal complexes can be used. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: OXD-8), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-9 ... Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. The substances mentioned here are mainly 10 －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.

[0304] (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 containing an organic compound and 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 at transporting the generated electrons. Specifically, the above-mentioned materials constituting the electron transport layer (e.g., metal complexes and heteroaromatic compounds) 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. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0305] (Layer Formation Method) The method for forming each layer of the organic EL element according to any of the above-described embodiments 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.

[0306] (Film Thickness) The film thickness of each organic layer of the organic EL element according to this embodiment is not limited unless specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer of the organic EL element is usually preferably in the range of several nm to 1 μm.

[0307] [Second Embodiment] The configuration of an organic EL element according to a second embodiment will be described. In the description of the second embodiment, the same components as those in the first embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the second embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first embodiment can be used.

[0308] The organic EL device according to the second embodiment differs from the organic EL device according to the first embodiment in that the emitting layer further contains a second host material. Other features are the same as those of the first embodiment. In this specification, the compound used as the second host material may be referred to as Compound M1. In one embodiment, the emitting layer contains a second host material (Compound M1), a first host material (Compound M2), and a fluorescent material (Compound M3).

[0309] (Light-emitting layer) In one embodiment, the second host material, the first host material, and the fluorescent material are contained in a single layer. In one embodiment, the second host material, the sensitizing material as the first host material, and the fluorescent material are contained in a single layer. For example, when the organic EL element has one light-emitting layer, the second host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer. When the organic EL element has multiple light-emitting layers, the second host material, the sensitizing material, and the fluorescent material are contained in any one of the multiple light-emitting layers.

[0310] 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.

[0311] [Second Host Material] In the second embodiment, the second host material is a 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 (1101) to (1118):

[0312]

[0313]

[0314] (In the general formula (1101), A １１ ~A １６ are each independently a nitrogen atom, CR １１ or a carbon atom bonded to another atom or other structure in the molecule of the compound M1, １１ ~A １６ At least one of R is a carbon atom bonded to another atom or another structure in the molecule of the compound M1, 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 (1102), １ ~A ４ are each independently a nitrogen atom, CR １２ or a carbon atom bonded to another atom or other structure in the molecule of the compound M1, 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 １２ one 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 compound M1, R １８and a carbon atom bonded to another atom or another structure in the molecule of the compound M1, or R １９ and a silicon atom bonded to another atom or another structure in the molecule of the compound M1, 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 compound M1, 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 (1103), 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 (1101) to (1104), R １１ , R １２ , R １４ , R １５ , R １６ , R １７ , R １１５ and R １１６ , and R １３ , R １８ , R １９ and R １１７are 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 (1103) to (1118), * represents a bonding site to another atom or another structure in the molecule of the compound M1, and when the compound M1 has a plurality of partial structures represented by the general formulae (1101) to (1104), the plurality of partial structures represented by the general formulae (1101) are the same or different from each other, the plurality of partial structures represented by the general formulae (1102) are the same or different from each other, the plurality of partial structures represented by the general formulae (1103) are the same or different from each other, and the plurality of partial structures represented by the general formula (1104) are the same or different from each other.

[0315] (In the compound M1, 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 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 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 ９１４If 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.)

[0316] In the general formula (1102), X １０ is "a nitrogen atom bonded to another atom or another structure in the molecule of compound M1", the general formula (1102) 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 compound M1, the general formula (1102) is represented by the following general formula (102-2). １０ "R １９ and a silicon atom bonded to another atom or another structure in the molecule of compound M1, the general formula (1102) is represented by the following general formula (102-3). １ ~A ４ are each independently A in the general formula (1102). １ ~A ４ is synonymous with R １８ and R １９ are each independently R in the general formula (1102). １２ and * indicates a bonding site to another atom or other structure in the molecule of compound M1.

[0317]

[0318] In one embodiment, the second host material has at least one partial structure represented by the general formula (1101). In one embodiment, the partial structure represented by the general formula (1101) is at least one selected from the group consisting of partial structures represented by the following general formulae (A11) to (A19):

[0319]

[0320]

[0321] (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 (1101). １１ and * represents a bonding site to another atom or another structure in the molecule of the compound M1. 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 other structure in the molecule of the compound M1, R １１ are each independently R in the general formula (1101). １１ is synonymous with A １１ ~A ２２ at least one of A is a carbon atom bonded to another atom or another structure in the molecule of the compound M1, １１ ~A １８ are each independently a nitrogen atom or CR １１ or a carbon atom bonded to another atom or other structure in the molecule of the compound M1, R １１ are each independently R in the general formula (1101). １１ is synonymous with X １１ and X １２ are each independently X in the general formula (1102). １０ and A １１ ~A １８ Carbon atoms in X１１ 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 the general formulas (A11) to (A19) is bonded to another atom or another structure in the molecule of the compound M1, and * in the general formulas (A11) to (A19) is a bonding site to another atom or another structure in the molecule of the compound M1.

[0322] In one embodiment, the second host material has at least one partial structure represented by the general formula (1102). In one embodiment, the partial structure represented by the general formula (1102) is at least one selected from the group consisting of partial structures represented by the following general formulas (B11) to (B24):

[0323]

[0324] (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 (1102). １２ is synonymous with X １０ represents X in the general formula (1102). １０ * is a bonding site to another atom or another structure in the molecule of the compound M1; and in the 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 other structure in the molecule of the compound M1, R １２ are each independently R in the general formula (1102). １２ is synonymous with X １０ represents X in the general formula (1102). １０ where Ax １ , Ax ２and 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 compound M1, １ ~Ay ８ are each independently a nitrogen atom or CR １２ or a carbon atom bonded to another atom or other structure in the molecule of the compound M1, R １２ are each independently R in the general formula (1102). １２ is synonymous with X １０ represents X in the general formula (1102). 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 the general formulas (B11) to (B18) is bonded to another atom or another structure in the molecule of the compound M1, and * in the general formulas (B11) to (B18) is a bonding site to another atom or another structure in the molecule of the compound M1.

[0325]

[0326] (In the general formulae (B19) to (B24), Ay １ ~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 other structure in the molecule of the compound M1, R １２ are each independently R in the general formula (1102). １２ is synonymous with X ９ and X １０ are each independently X in the general formula (1102). １０ Ay is synonymous with １ ~Ay８ 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 compound M1.

[0327] In the compound M1 of this 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 １２ and R １１５ ~R １１７are 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.

[0328] In the first compound of this 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 like) 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 １９ are 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 in１３ ~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.

[0329] Examples of the partial structure represented by any one of the general formulae (1101) to (1118) include partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125). It is also preferable that compound M1 contains at least one of the partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125) in one molecule.

[0330]

[0331] In the general formulae (A101) to (A107), R １０１ ~R １０６ are each independently R in the general formula (1101). 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 １０１ 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.

[0332]

[0333] In the general formulae (A108) and (A109), R １１０are each independently R in the general formula (1101). 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 compound M1, 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.

[0334]

[0335] In the general formulae (A110) to (A114), R １１０ and R １１２ ~R １１４ are each independently R in the general formula (1101). １１ is synonymous with X １１０ are each independently X in the general formula (1102). １０ where R １１０ and R １１２ ~R １１４ At least one of X is a single bond that bonds to another atom or another structure in the molecule of the compound M1, or １１０ At least one of the nitrogen atom, carbon atom, and silicon atom in the compound M1 is bonded to another atom or another structure in the compound M1, 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 in １４ 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 １７one 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.

[0336]

[0337] In the general formulae (A115) to (A119), R １１０ and R １１２ ~R １１４ are each independently R in the general formula (1101). 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 compound M1, 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.

[0338]

[0339] In the general formulae (A120) and (A121), R １１０ are each independently R in the general formula (1101). 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 compound M1, １１０ In 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.

[0340]

[0341] In the general formulae (B101) to (B109), R １１４ and R １２１ ~R １３１ are each independently R in the general formula (1102). 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 compound M1. 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 R １２７ Group R １２７ and R １２８ Group R １２８ and R １２９ Group R １２９ and R １１４ and R １１４ and R １２４In 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.

[0342]

[0343] In the general formulae (B110) to (B117), R １１０ and R １３２ ~R １３５ are each independently R in the general formula (1102). 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 compound M1, 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.

[0344]

[0345] In the general formulae (B118) to (B123), R １１０ are each independently R in the general formula (1102). １２ Xa and Xb each independently represent X in the general formula (1102). １０ where R１１０ 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 compound M1, 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 compound M1, 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.

[0346]

[0347] In the general formulae (B124) and (B125), R １１０ are each independently R in the general formula (1102). １２ Xa, Xb, and Xc each independently represent X in the general formula (1102). １０ where R １１０ 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 compound M1, 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 compound M1, and a plurality of R １１０ In the general formulae (B124) and (B125), a plurality of R １１０and 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.

[0348] 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 an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0349] 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 １９and 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.

[0350] In this embodiment, compound M1 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) at least one 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.

[0351] In this embodiment, it is more preferable that the compound M1 (III) has at least one cyano group, or (IV) has 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.

[0352] In this embodiment, it is more preferable that the compound M1 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.

[0353] In this embodiment, the compound M1 preferably has at least one monovalent or higher valent residue derived from a substituted or unsubstituted carbazole.

[0354] In this embodiment, the compound M1 preferably has at least one partial structure represented by the following general formula (15).

[0355]

[0356] (In the general formula (15), R １５０ ~R １５８ At least one of R is a single bond that bonds to another atom or another structure in the molecule of the compound M1, 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 ) (R９０３ 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.

[0357] 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.

[0358] (Compound M1 Represented by General Formula (161) or (162)) In this embodiment, compound M1 is also preferably a compound represented by the following general formula (161) or (162).

[0359]

[0360] (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.

[0361] 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).

[0362]

[0363] In this 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):

[0364]

[0365] (In the general formula (DN7), * represents Ar １６１ It represents the bonding site with the elements that make up the molecule.)

[0366] In this 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).

[0367]

[0368]

[0369] (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 compound M1, 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 (1102). 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.)

[0370] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (13).

[0371]

[0372] (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.

[0373] 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:

[0374] 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.

[0375] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (12):

[0376]

[0377] (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.

[0378] 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.

[0379] 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.

[0380] 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.

[0381] 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).

[0382]

[0383] (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 are respectively 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).

[0384] 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.

[0385] 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.

[0386] In one embodiment, the light-emitting layer may contain two or more compounds M1 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 light-emitting efficiency is expected. Furthermore, by forming an exciplex between two or more compounds M1 (second host materials), the excitation energy is reduced, enabling lower voltage driving than when a single second host material is contained in the light-emitting layer.

[0387] (Method for Producing Compound M1) Compound M1 can be produced by a known method. Compound M1 can also be produced by following a known method and using known alternative reactions and raw materials suited to the target product.

[0388] (Specific Examples of Compound M1) Specific examples of compound M1 of this embodiment include the following compounds: However, the present invention is not limited to these specific examples of compounds.

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396] (Relationship between second host material, sensitizer material, and fluorescent material in the emitting layer) In one embodiment, the sensitizer material serving as the first host material is the delayed fluorescent compound. FIG. 5 is a diagram showing an example of the relationship between the energy levels of the second host material, the sensitizer material, and the fluorescent material when the emitting layer includes a second host material (compound M1), a delayed fluorescent compound (compound M2) serving as a sensitizer material, and a fluorescent material (compound M3). In FIG. 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the second host material, and T1(M1) represents the lowest excited triplet state of the second 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%.

[0397] In one embodiment, the energy gap T at 77 K of the second host material ７７Ｋ (H2) and the energy gap T at 77 [K] of the sensitizing material ７７Ｋ (G2) preferably satisfy the relationship of the following formula (Formula 10): T ７７Ｋ (H2)>T ７７Ｋ (G2) ...(Number 10)

[0398] In one embodiment, the lowest excited singlet energy S of the second host material １ (H2) and the lowest excited singlet energy S of the sensitizing material １ It is also preferable that (GT2) satisfies the relationship of the following mathematical formula (Mathematical Formula 4A): S １ (H2)>S １ (GT2) ... (Math 4A)

[0399] In one embodiment, the lowest excited singlet energy S of the second 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 (H2)>S １ (GT2)>S １ (D) ... (Math 4B)

[0400] In one embodiment, the energy gap T at 77 [K] of the second 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 (H2)>T ７７Ｋ (GT2)>T ７７Ｋ (D) ...(Math 6B)

[0401] (Compound Contents in Emitting Layer) The contents of the second host material (compound M1), the first host material (compound M2), and the fluorescent material (compound M3) contained in the emitting layer are preferably within the following ranges, for example. The content of compound M1 in the emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more. The content of compound M1 in the emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.

[0402] The content of 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.

[0403] The content of compound M3 in the light-emitting layer is preferably 0.5% by mass or more, and more preferably 1% by mass or more. The content of compound M3 in the light-emitting layer is preferably 10% by mass or less, and more preferably 5% by mass or less. The upper limit of the total content of compounds M1, M2, and M3 in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the inclusion of materials other than compounds M1, M2, and M3 in the light-emitting layer. In this embodiment, the light-emitting layer may contain only one type of compound M1, or two or more types. In this embodiment, the light-emitting layer may contain only one type of compound M2, or two or more types. In this embodiment, the light-emitting layer may contain only one type of compound M3, or two or more types. According to the second embodiment, an organic EL element that emits light with high efficiency can be realized. The organic EL element according to the second embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0404] (Thickness of 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. A thickness of 5 nm or more facilitates the formation of the light-emitting layer and the adjustment of chromaticity, while a thickness of 50 nm or less facilitates the suppression of an increase in driving voltage.

[0405] The organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0406] [Third Embodiment] (Electronic Device) An electronic device according to a third embodiment is equipped with an organic EL element according to any of the above-described embodiments. The electronic device according to the third embodiment may be equipped with an organic EL element according to any of the fourth 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 fixtures. The light-emitting device can be used in a display device, and can also be used, for example, as a backlight for a display device.

[0407] The display device as the electronic device according to the third embodiment is preferably an organic EL display device having organic EL elements mounted thereon as red, green, and blue pixels. In the organic EL display device, the blue pixel is preferably an organic EL element according to the first, second, or fourth embodiment, or an organic EL element using the compound according to the fifth embodiment. In the organic EL display device, the red and green pixels may each independently be an organic EL element according to the first, second, or fourth embodiment, or an organic EL element using the compound according to the fifth embodiment.

[0408] [Fourth embodiment] An organic EL device according to a fourth embodiment includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode, the emitting layer may include a compound M2 represented by general formula (1) as a first host material, and a phosphorescent metal complex as a dopant material. An organic EL device according to the fourth embodiment includes an anode, a cathode, and an emitting layer disposed between the anode and the cathode, the emitting layer may include a compound M2 represented by general formula (1) as a first host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material (compound M3) as a dopant material.

[0409] (Phosphorescent Metal Complex) In one embodiment, the phosphorescent metal complex preferably contains a heavy metal atom.

[0410] 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).

[0411] 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)

[0412]

[0413] 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 ２ is 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 ４The 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(R２５６ ) (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 ) (R ２６７ 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.

[0414] 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.

[0415] 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 (carbon 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).

[0416] 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.

[0417] 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.

[0418] 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.

[0419] 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.

[0420] 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.

[0421] 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.

[0422] 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."

[0423] 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."

[0424] 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.

[0425] 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).

[0426] 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.

[0427] 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.

[0428] 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.

[0429] 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.

[0430] 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).

[0431]

[0432]

[0433] In the general formulae (10-1) to (10-61), * indicates the bonding position to the adjacent atom.

[0434] 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.

[0435] 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.

[0436] 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.

[0437] 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.

[0438] In the organic EL element according to the fourth embodiment, the light-emitting layer contains the compound M2 represented by the general formula (1), and therefore, according to the fourth embodiment, high efficiency of the organic EL element can be realized. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0439] Fifth Embodiment (Compound) A compound according to a fifth embodiment is a compound represented by the following general formula (100).

[0440]

[0441]

[0442] (In the general formula (100), Ar １００ is a group represented by the following general formula (1A), １００ When there are multiple Ar １００ are the same or different from each other, and Y １ ~Y ３are each independently a nitrogen atom or CH, provided that Y １ ~Y ３ two or more of the rings B, C, D and E are nitrogen atoms, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms, and Z ２ and Z ３ are each independently a single bond, C(R １ ) (R ２ ), N.R. ３ , an oxygen atom, or a sulfur atom; Z ２ and Z ３ are the same or different from each other, Ar １ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), m is 1, 2, 3, 4 or 5, n is 0, 1, 2, 3 or 4, m+n=5, and when n is 2, 3 or 4, a plurality of Ar １ are the same or different, *1 and *2 each represent a bonding position to a benzene ring, and in the general formula (2), Z is C(R １Ａ ) (R ２Ａ ), N.R. ３Ａ , an oxygen atom, or a sulfur atom; R １１ ~R １８ one or more pairs of adjacent two or more of Ar 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, with the proviso that Ar １ is a group represented by the general formula (2), R １１ ~R １８ and R ３Ａ is a single bond to the benzene ring in the general formula (100), １ , R ２ , R ３ , R １Ａ , R ２Ａand R which is not a single bond to the benzene ring, does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring. ３Ａ , and R １１ ~R １８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ a group represented by —O—(R ９０４ ), a group represented by —S—(R ９０５ a group represented by —N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and in the compound represented by the general formula (100), R 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, 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, R９０６ 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.)

[0443]

[0444] (In the general formula (1A), Z １ represents Z in the general formula (100). ２ and X １ ~X ４ are each independently a nitrogen atom or CRx, １ ~X ４ at least one of the rings is a nitrogen atom, the ring A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms, and Rx is R in the general formula (2). １１ ~R １８ When a plurality of A rings are present, the plurality of A rings are the same as or different from each other; When a plurality of Rx's are present, the plurality of Rx's are the same as or different from each other; When a plurality of groups represented by the general formula (1A) are present, the plurality of groups represented by the general formula (1A) are the same as or different from each other; *1 indicates the bonding position with the benzene ring in the general formula (100). １ ~Y ３ are nitrogen atoms, and in the general formula (100), at least one Ar １００ is a group represented by any one of the following general formulas (100A), (100B), (100C) and (100D), the general formula (100) satisfies at least one of the following requirements (i), (ii) and (iii): (i) at least one Ar １００ is a group represented by the following general formula (100A), m is 2, 3, 4 or 5, or n is 1, and one Ar １ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), or n is 2 and two Ar１ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a group represented by the general formula (2), or n is 3 and three Ar １ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), or n is 4 and four Ar １ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2). １００ is a group represented by the following general formula (100B), (100C) or (100D), at least one group represented by the following general formula (100B), (100C) or (100D) is bonded to the carbon atom at the position a in the general formula (100). １００ is a group represented by the following general formula (100B), (100C), or (100D), ring B, ring C, ring D, and ring E are each independently an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocycle having 5 to 60 ring atoms.

[0445]

[0446] (In the general formulae (100A), (100B), (100C) and (100D), R ３１１ ~R ３１４ 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 to form the substituted or unsubstituted monocycle and the substituted or unsubstituted fused ring ３１１ ~R ３１４ are each independently R in the general formula (2). １１ ~R １８wherein ring A is the same as ring A in general formula (1A); when a plurality of rings A are present, the plurality of rings A are the same as or different from one another; when a plurality of groups represented by general formula (100A) are present, the plurality of groups represented by general formula (100A) are the same as or different from one another; when a plurality of groups represented by general formula (100B) are present, the plurality of groups represented by general formula (100B) are the same as or different from one another; when a plurality of groups represented by general formula (100C) are present, the plurality of groups represented by general formula (100C) are the same as or different from one another; when a plurality of groups represented by general formula (100D) are present, the plurality of groups represented by general formula (100D) are the same as or different from one another; *1 indicates the bonding position to the benzene ring in general formula (100).

[0447] In the compound of the fifth embodiment, Z ２ and Z ３ is preferably a single bond.

[0448] In the compound of the fifth embodiment, it is preferable that ring A is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted dibenzothiophene ring. In the compound of the fifth embodiment, it is preferable that ring B, ring C, ring D, and ring E are each independently a substituted or unsubstituted benzene ring, or a substituted or unsubstituted dibenzothiophene ring. In the compound of the fifth embodiment, when at least one of the requirements (i) and (ii) is satisfied, it is preferable that ring B, ring C, ring D, and ring E are each independently a substituted or unsubstituted benzene ring, or a substituted or unsubstituted dibenzothiophene ring, and when the requirement (iii) is satisfied, it is preferable that ring B, ring C, ring D, and ring E are each independently an unsubstituted benzene ring, or an unsubstituted dibenzothiophene ring.

[0449] In the compound of the fifth embodiment, X １ ~X ３ is a nitrogen atom, and X is not a nitrogen atom １ ~X ４ is preferably CRx.

[0450] In the compound of the fifth embodiment, X ２ or X ４ is a nitrogen atom, and X is not a nitrogen atom １ ~X ４ is preferably CRx.

[0451] In the compound of the fifth embodiment, Y ２ and Y ３ are nitrogen atoms, and Y １ is CH, or Y １ ~Y ３ It is preferred that three of the above are nitrogen atoms.

[0452] In the compound of the fifth embodiment, Y １ ~Y ３ It is preferred that three of the above are nitrogen atoms.

[0453] In the compound of the fifth embodiment, Ar １ is preferably a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0454] In the compound of the fifth embodiment, Ar １００ is a group represented by the general formula (100B), (100C) or (100D), m is preferably 1.

[0455] In the compound of the fifth embodiment, Ar １００ is preferably a group represented by any one of the general formulas (100A), (100B), (100C) and (100D). １００ When there are multiple Ar １００are preferably the same as each other. In the compound of the fifth embodiment, the groups represented by the general formulae (100A), (100B), (100C), and (100D) are preferably the groups represented by the general formulae (11A), (12A), (13A), and (14A) described in the compound M2 of the first embodiment, respectively. However, in the general formulae (11A), (12A), (13A), and (14A), *1 has the same meaning as *1 in the general formula (1A). In the compound of the fifth embodiment, the groups represented by the general formulae (100A), (100B), (100C), and (100D) are preferably the groups represented by the general formulae (15A), (16A), (17A), and (18A) described in the compound M2 of the first embodiment, respectively. In the general formulae (15A), (16A), (17A) and (18A), *1 has the same meaning as *1 in the general formula (1A).

[0456] In the compound of the fifth embodiment, in the compound represented by the general formula (100), it is preferable that the partial structure represented by the following general formula (1B) and the partial structure represented by the following general formula (1C) are each independently a group represented by any one of the general formulae (11B) to (13B) described in the compound M2 of the first embodiment. The partial structure represented by the following general formula (1B) and the partial structure represented by the following general formula (1C) are the same as or different from each other.

[0457]

[0458] (In the general formulae (1B) and (1C), ring B, ring C, ring D, ring E, Z ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *3 represents the same as the Y １ and Y ３ *4 indicates the bonding position to the carbon atom between the Y ２ and Y ３ This indicates the bond position to the carbon atom between

[0459] In the compound of the fifth embodiment, in the compound represented by the general formula (100), it is also preferable that the partial structure represented by the general formula (1B) and the partial structure represented by the general formula (1C) are each independently a group represented by the general formula (14B) or (15B) described in the compound M2 of the first embodiment. In the general formulas (11B) to (15B), *5 has the same meaning as *3 in the general formula (1B) or *4 in the general formula (1C).

[0460] In one aspect of the fifth embodiment, m is 1, 2, 3, or 4. In one aspect of the fifth embodiment, m is 1, 2, or 3. In one aspect of the fifth embodiment, m is 1 or 2. In one aspect of the fifth embodiment, m is 1.

[0461] The compound of the fifth embodiment is preferably a compound represented by any one of the following general formulas (110A) to (125A).

[0462]

[0463] (In the general formula (110A), m1 is 2, 3, 4, or 5, n1 is 0, 1, 2, or 3, m1+n1=5, and R ３１２ ~R ３１８ respectively represent R in the general formula (11A). ３１２ ~R ３１８ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y ３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0464]

[0465] (In the general formula (111A), m1 is 2, 3, 4, or 5, n1 is 0, 1, 2, or 3, and m1+n1=5; A １ Tamaki, A ２ Ring, R ３１２ ~R ３１４ and R ４１１ ~R ４１４ respectively represent A in the general formula (15A). １ Tamaki, A ２ Ring, R ３１２ ~R ３１４ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y ３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0466]

[0467] (In the general formula (112A), m2 is 1, 2, 3, or 4, n2 is 1, 2, 3, or 4, and m2 + n2 is 2, 3, 4, or 5; Ar １Ａ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a group represented by the general formula (2), and Ar １Ａ When there are multiple Ar １Ａ are the same or different from each other, R ３１２ ~R ３１８ respectively represent R in the general formula (11A). ３１２ ~R ３１８ is synonymous with Y １ ~Y ３ are Y in the general formula (100), respectively. １ ~Y ３ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above.２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ and *1 and *2 are respectively defined as *1 and *2 in the general formula (100).) In the general formula (112A), when m2 is 1, n2 is 1, 2, 3, or 4, when m2 is 2, n2 is 1, 2, or 3, when m2 is 3, n2 is 1 or 2, and when m2 is 4, n2 is 1. For example, when m2 is 1 and n2 is 1, in the general formula (112A), one azacarbazolyl group and one Ar are present at two positions (carbon atoms) selected from a to e. １Ａ and are bonded to each other, and the azacarbazolyl group and Ar １Ａ For example, when m2 is 1 and n2 is 2, one azacarbazolyl group and two Ar are bonded to three positions (carbon atoms) selected from a to e in the general formula (112A). １Ａ and are bonded to each other, and the azacarbazolyl group and Ar １Ａ The remaining two positions (carbon atoms) that are not bonded to a hydrogen atom are bonded to hydrogen atoms.

[0468]

[0469] (In the general formula (113A), m2 is 1, 2, 3, or 4, n2 is 1, 2, 3, or 4, and m2 + n2 is 2, 3, 4, or 5; Ar １Ａ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a group represented by the general formula (2), and Ar １Ａ When there are multiple Ar １Ａ are the same or different from each other, １ Tamaki, A ２ Ring, R ３１２ ~R ３１４ and R ４１１ ~R ４１４ respectively represent A in the general formula (15A). １ Tamaki, A ２ Ring, R ３１２ ~R３１４ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ are Y in the general formula (100), respectively. １ ~Y ３ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ and *1 and *2 are respectively defined as *1 and *2 in the general formula (100).) In the general formula (113A), when m2 is 1, n2 is 1, 2, 3, or 4; when m2 is 2, n2 is 1, 2, or 3; when m2 is 3, n2 is 1 or 2; and when m2 is 4, n2 is 1.

[0470]

[0471] In the general formula (114A), m3 is 0, 1, 2, 3, or 4, n3 is 0, 1, 2, 3, or 4, m3 + n3 = 4, and Ar １００Ａ is a group represented by the general formula (12A), and Ar １００Ａ When there are multiple Ar １００Ａ are the same or different from each other, R ３１１ and R ３１３ ~R ３１８ respectively represent R in the general formula (12A). ３１１ and R ３１３ ~R ３１８ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y ３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３*1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0472]

[0473] In the general formula (115A), m3 is 0, 1, 2, 3, or 4, n3 is 0, 1, 2, 3, or 4, m3 + n3 = 4, and Ar １００Ａ is a group represented by the general formula (16A), and Ar １００Ａ When there are multiple Ar １００Ａ are the same or different from each other, １ Tamaki, A ２ Ring, R ３１１ , R ３１３ , R ３１４ and R ４１１ ~R ４１４ respectively represent A in the general formula (16A). １ Tamaki, A ２ Ring, R ３１１ , R ３１３ , R ３１４ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y ３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0474] In the general formula (116A), m3 is 0, 1, 2, 3, or 4, n3 is 0, 1, 2, 3, or 4, m3 + n3 = 4, and Ar １００Ａ is a group represented by the general formula (13A), and Ar １００Ａ When there are multiple Ar １００Ａare the same or different from each other, R ３１１ , R ３１２ and R ３１４ ~R ３１８ respectively represent R in the general formula (13A). ３１１ , R ３１２ and R ３１４ ~R ３１８ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y ３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0475]

[0476] In the general formula (117A), m3 is 0, 1, 2, 3, or 4, n3 is 0, 1, 2, 3, or 4, m3 + n3 = 4, and Ar １００Ａ is a group represented by the general formula (17A), and Ar １００Ａ When there are multiple Ar １００Ａ are the same or different from each other, １ Tamaki, A ２ Ring, R ３１１ , R ３１２ , R ３１４ and R ４１１ ~R ４１４ respectively represent A in the general formula (17A). １ Tamaki, A ２ Ring, R ３１１ , R ３１２ , R ３１４ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0477] (In the general formula (118A), m3 is 0, 1, 2, 3, or 4, n3 is 0, 1, 2, 3, or 4, and Ar １００Ａ is a group represented by the general formula (14A), and Ar １００Ａ When there are multiple Ar １００Ａ are the same or different from each other, R ３１１ ~R ３１３ and R ３１５ ~R ３１８ respectively represent R in the general formula (14A). ３１１ ~R ３１３ and R ３１５ ~R ３１８ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y ３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0478]

[0479] In the general formula (119A), m3 is 0, 1, 2, 3, or 4, n3 is 0, 1, 2, 3, or 4, m3 + n3 = 4, and Ar １００Ａ is a group represented by the general formula (18A), and Ar １００ＡWhen there are multiple Ar １００Ａ are the same or different from each other, １ Tamaki, A ２ Ring, R ３１１ ~R ３１３ and R ４１１ ~R ４１４ respectively represent A in the general formula (18A). １ Tamaki, A ２ Ring, R ３１１ ~R ３１３ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ and Ar １ are Y in the general formula (100), respectively. １ ~Y ３ and Ar １ and the ring B, ring C, ring D, ring E, and ring Z are the same as those shown in the above. ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (100). ２ and Z ３ *1 and *2 have the same meanings as *1 and *2 in the general formula (100), respectively.)

[0480]

[0481] (In the general formula (120A), R ３１１ and R ３１３ ~R ３１８ respectively represent R in the general formula (12A). ３１１ and R ３１３ ~R ３１８ is synonymous with Y １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ are Y in the general formula (100), respectively. １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ring B10, ring C10, ring D10, and ring E10 each independently represent an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocyclic ring having 5 to 60 ring atoms, and *1 and *2 are respectively defined as *1 and *2 in general formula (100).

[0482]

[0483] (In the general formula (121A), A １ Tamaki, A ２ Ring, R ３１１ , R ３１３ , R ３１４ and R ４１１ ~R ４１４ respectively represent A in the general formula (16A). １ Tamaki, A ２ Ring, R ３１１ , R ３１３ , R ３１４ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ are Y in the general formula (100), respectively. １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ ring B10, ring C10, ring D10 and ring E10 each independently represent an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocyclic ring having 5 to 60 ring atoms, and *1 and *2 are respectively defined as *1 and *2 in general formula (100).

[0484]

[0485] (In the general formula (122A), R ３１１ , R ３１２ and R ３１４ ~R ３１８ respectively represent R in the general formula (13A). ３１１ , R ３１２ and R ３１４ ~R３１８ is synonymous with Y １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ are Y in the general formula (100), respectively. １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ ring B10, ring C10, ring D10 and ring E10 each independently represent an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocyclic ring having 5 to 60 ring atoms, and *1 and *2 are respectively defined as *1 and *2 in general formula (100).

[0486]

[0487] (In the general formula (123A), A １ Tamaki, A ２ Ring, R ３１１ , R ３１２ , R ３１４ and R ４１１ ~R ４１４ respectively represent A in the general formula (17A). １ Tamaki, A ２ Ring, R ３１１ , R ３１２ , R ３１４ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ are Y in the general formula (100), respectively. １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ ring B10, ring C10, ring D10 and ring E10 each independently represent an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocyclic ring having 5 to 60 ring atoms, and *1 and *2 are respectively defined as *1 and *2 in general formula (100).

[0488]

[0489] (In the general formula (124A), R ３１１ ~R ３１３ and R ３１５ ~R ３１８ respectively represent R in the general formula (14A). ３１１ ~R ３１３ and R ３１５ ~R ３１８ is synonymous with Y １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ are Y in the general formula (100), respectively. １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ ring B10, ring C10, ring D10 and ring E10 each independently represent an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocyclic ring having 5 to 60 ring atoms, and *1 and *2 are respectively defined as *1 and *2 in general formula (100).

[0490]

[0491] (In the general formula (125A), A １ Tamaki, A ２ Ring, R ３１１ ~R ３１３ and R ４１１ ~R ４１４ respectively represent A in the general formula (18A). １ Tamaki, A ２ Ring, R ３１１ ~R ３１３ and R ４１１ ~R ４１４ is synonymous with Y １ ~Y ３ , Ar １ , m, n, Z ２ and Z ３ are Y in the general formula (100), respectively. １ ~Y ３ , Ar １ , m, n, Z ２and Z ３ ring B10, ring C10, ring D10 and ring E10 each independently represent an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocyclic ring having 5 to 60 ring atoms, and *1 and *2 are respectively defined as *1 and *2 in general formula (100).

[0492] In the general formulae (110A) to (125A), Y １ ~Y ３ It is preferred that three of the above are nitrogen atoms.

[0493] In the compound of the fifth embodiment, R １ , R ２ , R ３ , R １Ａ , R ２Ａ , R ３Ａ , R １１ ~R １８ and R ３１１ ~R ３１４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ３１５ ~R ３１８ and R ４１１ ~R ４１４ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0494] In one aspect of the fifth embodiment, the compound represented by the general formula (100) contains at least one deuterium atom. In one aspect of the fifth embodiment, the compound represented by the general formula (100) does not contain a deuterium atom.

[0495] In the compound of the fifth embodiment, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ and R９０７ 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.

[0496] In the compound of the fifth 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. In the compound of the fifth embodiment, the substituent in the case of "substituted or unsubstituted" is more 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. In the compound of the fifth embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0497] The compound of the fifth embodiment allows an organic EL device to emit light with high efficiency.

[0498] [Organic EL element] An organic EL element using the compound according to the fifth embodiment (hereinafter also referred to as organic EL element E1) includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a compound represented by the general formula (100). In the organic EL element E1, the organic layer preferably has at least one light-emitting layer, and the at least one light-emitting layer preferably includes a compound represented by the general formula (100). The compound according to the fifth embodiment is a compound that can cause the organic EL element E1 to emit light with high efficiency. Therefore, the organic EL element E1 emits light with high efficiency.

[0499] Specific examples of the compound according to the fifth embodiment include compounds that satisfy the conditions of the general formula (100) among the compounds exemplified as compound M2 in the first embodiment, although the present invention is not limited to these specific examples of compounds.

[0500] Sixth Embodiment Material for Organic EL Device The material for an organic EL device of the sixth embodiment contains the compound M2 of the first embodiment or the compound of the fifth embodiment (the compound represented by the general formula (100)). The material for an organic EL device of the sixth embodiment makes it possible to realize an organic EL device and an electronic device that emit light with high efficiency. The material for an organic EL device of the sixth embodiment may further contain other compounds. When the material for an organic EL device of the sixth embodiment further contains other compounds, the other compounds may be solid or liquid.

[0501] [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.

[0502] 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.

[0503] 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.

[0504] 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.

[0505] 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.

[0506] <Compound> The structure of the compound M2 represented by general formula (1) used in the production of the organic EL devices according to Examples 1 to 8 is shown below.

[0507]

[0508]

[0509]

[0510] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1 to 3 are shown below.

[0511]

[0512] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 8 and Comparative Examples 1 to 3 are shown below.

[0513]

[0514]

[0515] <Preparation of Organic EL Device (1)> Organic EL devices were prepared as follows and evaluated.

[0516] Example 1 On a glass substrate, a 100 nm-thick silver alloy layer, an APC (Ag—Pd—Cu) layer, and a 10 nm-thick indium oxide-zinc oxide (IZO) layer were formed in this order by sputtering. This resulted in a conductive material layer consisting of an APC layer and an IZO layer. The APC layer was a light-reflecting layer, and the IZO layer was a transparent conductive layer. IZO is a registered trademark. Subsequently, using conventional lithography techniques, the conductive material layer consisting of a light-reflecting layer and a transparent conductive layer was patterned by etching using a resist pattern as a mask to form an anode. The substrate on which the lower electrode (anode) was formed was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. Next, compound HT-1 and compound HA were co-deposited on the lower electrode (anode) using a vacuum deposition method to form a 10 nm-thick hole injection layer. The proportion of compound HT-1 in the hole injection layer was 97% by mass, and the proportion of compound HA 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 115 nm. Next, compound EBL-1 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. The second hole transport layer is sometimes referred to as an electron blocking layer. Next, compound Matrix-1 (compound M1) as a host material, compound TADF1 (compound M2) as a sensitizing material, and compound BD-1 (compound M3) as a fluorescent material were co-deposited on the second hole transport layer to form an emitting layer with a film thickness of 31 nm. The proportion of compound Matrix-1 in this emitting layer was 73.8% by mass, the proportion of compound TADF1 was 25% by mass, and the proportion of compound BD-1 was 1.2% by mass. Next, compound HBL-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer with a thickness of 5 nm. The first electron-transporting layer may also be referred to as a hole-blocking layer. Compound ET-1 and compound Liq were co-deposited on the first electron-transporting layer to form a second electron-transporting layer with a thickness of 31 nm. The proportion of compound ET-1 in this second electron-transporting layer was 50 mass %, and the proportion of compound Liq was 50 mass %. Liq is an abbreviation for (8-quinolinolato)lithium.Ytterbium (Yb) was vapor-deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. A film of Mg and Ag was vapor-deposited on the electron injection layer at a mixing ratio (mass %) of 10:90 to form a semi-transparent MgAg alloy upper electrode (cathode) with a thickness of 13 nm. Compound Cap-1 was vapor-deposited on the upper electrode (cathode) by vacuum deposition to form a capping layer with a thickness of 65 nm. In this manner, a top-emission organic EL device according to Example 1 was fabricated. The device configuration of Example 1 is schematically shown as follows: APC(100) / IZO(10) / HT-1:HA(10,97%:3%) / HT-1(115) / EBL-1(5) / Matrix-1:TADF1:BD-1(31,73.8:25%:1.2%) / HBL-1(5) / ET-1:Liq(31,50%:50%) / Yb(1) / Mg:Ag(13,10%:90%) / Cap-1(65) Note that in the above element configuration, the numbers in parentheses indicate the film thickness (unit: nm). With regard to the element configuration of Example 1, the figures expressed in percentage (97%:3%) in parentheses indicate the proportions (mass%) of Compound HT-1 and Compound HA in the hole injection layer, the figures expressed in percentage (73.8%:25%:1.2%) indicate the proportions (mass%) of Compound M1 (Compound Matrix-1), Compound M2 (Compound TADF1), and Compound M3 (Compound BD-1) in the light-emitting layer, the figures expressed in percentage (50%:50%) indicate the proportions (mass%) of Compound ET-1 and Liq in the second electron transport layer, and the figures expressed in percentage (10%:90%) indicate the mixing ratio (mass%) of Mg and Ag in the upper electrode (cathode).

[0517] (Examples 2 to 5 and Example 8) The organic EL devices of Examples 2 to 5 and Example 8 were fabricated in the same manner as the organic EL device of Example 1, except that the compound TADF1 used as the sensitizing material in forming the light-emitting layer was changed to the compound shown in Table 1.

[0518] Example 6 The organic EL element of Example 6 was fabricated in the same manner as the organic EL element of Example 1, except that the compound TADF1 used as the sensitizing material in forming the light-emitting layer was changed to the compound shown in Table 2.

[0519] (Example 7) The organic EL element of Example 7 was fabricated in the same manner as the organic EL element of Example 1, except that the compound TADF1 used as the sensitizing material in forming the light-emitting layer was changed to the compound shown in Table 3.

[0520] Comparative Example 1 The organic EL element of Comparative Example 1 was fabricated in the same manner as the organic EL element of Example 1, except that the compound TADF1 used as the sensitizing material in forming the light-emitting layer was changed to the compound shown in Table 1.

[0521] (Comparative Example 2) The organic EL element of Comparative Example 2 was fabricated in the same manner as the organic EL element of Example 1, except that the compound TADF1 used as the sensitizing material in forming the light-emitting layer was changed to the compound shown in Table 2.

[0522] (Comparative Example 3) The organic EL element of Comparative Example 3 was fabricated in the same manner as the organic EL element of Example 1, except that the compound TADF1 used as the sensitizing material in forming the light-emitting layer was changed to the compound shown in Table 3.

[0523] <Evaluation of Organic EL Device> The fabricated organic EL device was evaluated as follows. The evaluation results are shown in Tables 1 to 3.

[0524] (L / J / CIEy) The organic EL element thus fabricated was applied with a current density of 10 mA / cm ２ The spectral radiance spectrum when a voltage was applied so that the value was 0.05 was measured using a spectroradiometer CS-1000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the chromaticity CIEx, CIEy, and current efficiency L / J (unit: cd / A) were calculated. The value of "L / J / CIEy" was calculated by dividing the value of current efficiency L / J by the value of CIEy. The value of "L / J / CIEy" is sometimes referred to as the blue index (BI). In this evaluation, the value of the blue index (BI) was used as an index of luminous efficiency.

[0525] The "BI (relative value)" (unit: %) shown in Table 1 was calculated based on the BI value of each example (Examples 1 to 5, Example 8, and Comparative Example 1) and the following formula (Number X1): BI (relative value) = (BI of each example / BI of Comparative Example 1) × 100 (Number X1)

[0526] The "BI (relative value)" (unit: %) shown in Table 2 was calculated based on the BI value of each example (Example 6 and Comparative Example 2) and the following formula (Number X2): BI (relative value) = (BI of each example / BI of Comparative Example 2) × 100 (Number X2).

[0527] The "BI (relative value)" (unit: %) shown in Table 3 was calculated based on the BI value of each example (Example 7 and Comparative Example 3) and the following formula (Number X3): BI (relative value) = (BI of each example / BI of Comparative Example 3) × 100 (Number X3).

[0528]

[0529] In Examples 1 to 5 and Example 8, compounds TADF1 to 5 and TADF8 used as sensitizing materials have a structure in which an azine ring having two donor groups (carbazolyl groups) and a donor group (azacarbazolyl group) containing a nitrogen-containing six-membered ring structure are bonded to a benzene ring. Compound Ref-1 used as a sensitizing material in Comparative Example 1 is a compound in which the azacarbazolyl group in compound TADF1 is replaced with a carbazolyl group. Compound Ref-1 used as a sensitizing material in Comparative Example 1 is a compound in which the azacarbazolyl group in compound TADF8 is replaced with a carbazolyl group and the deuterium atom is replaced with a proton atom. The organic EL devices of Examples 1 to 5 and Example 8 emitted light with higher efficiency than the organic EL device of Comparative Example 1.

[0530]

[0531] The compound TADF6 used as the sensitizing material in Example 6 has a structure in which an azine ring having two donor groups (carbazolyl groups) and a donor group (azacarbazolyl group) containing a nitrogen-containing six-membered ring structure are bonded to a benzene ring. The compound Ref-2 used as the sensitizing material in Comparative Example 2 is a compound in which the azacarbazolyl group in the compound TADF6 is replaced with a carbazolyl group. The organic EL device of Example 6 emitted light with higher efficiency than the organic EL device of Comparative Example 2.

[0532]

[0533] The compound TADF7 used as the sensitizing material in Example 7 has a structure in which an azine ring having two donor groups (carbazolyl groups) and a donor group (azacarbazolyl group) containing a nitrogen-containing six-membered ring structure are bonded to a benzene ring. The compound Ref-3 used as the sensitizing material in Comparative Example 3 is a compound in which the azacarbazolyl group in the compound TADF7 is replaced with a carbazolyl group. The organic EL device of Example 7 emitted light with higher efficiency than the organic EL device of Comparative Example 3.

[0534] <Evaluation of Compounds> The compounds were evaluated as follows.

[0535] (Lowest excited singlet energy S １ A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) was measured at room temperature (300 K). A tangent line was drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis was substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S １ [eV]=1239.85 / λedge A spectrophotometer manufactured by Hitachi (device name: U3310) was used as the absorption spectrum measuring device.

[0536] 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.

[0537] (Energy gap T at 77[K] ７７ＫThe compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to obtain a solution, which was then placed in a quartz cell to serve as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent line was drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis was 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 / λ ｅｄｇｅ

[0538] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows. When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum among the spectral maxima, consider the tangent at each point on the curve toward the long wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope is at its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the shortest wavelength maximum, and the tangent drawn at the point where the slope is closest to the shortest wavelength maximum is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Phosphorescence was measured using an F-4500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation.

[0539] (ΔST) The lowest excited singlet energy S measured １ and the energy gap T ７７Ｋ Based on the value of ΔST=S １ -T ７７Ｋ It was confirmed that ΔST was less than 0.3 eV for the compounds TADF1 to TADF8 and the comparative compounds Ref-1 to Ref-3.

[0540] (Delayed Fluorescence of Compound) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 2. The compound TADF1 was 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 was frozen and degassed, then sealed in a capped cell under an argon atmosphere to produce an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation). The fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The fluorescence area intensities of both spectra were used to calculate the total fluorescence quantum yield according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the compound TADF1, there are prompt luminescence (immediate luminescence) that is observed immediately from the excited state, and delay luminescence (delayed luminescence) that is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence means that the amount of delay luminescence (delayed luminescence) is 5% or more of the amount of prompt luminescence (immediate luminescence). Specifically, the amount of prompt luminescence (immediate luminescence) is X Ｐ The amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X Ｐmeans that the value of is 0.05 or more. 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). The apparatus used to calculate the amounts of Prompt luminescence and Delay luminescence is not limited to the apparatus described in Reference 1 or the apparatus shown in Figure 2. Compounds TADF2 to TADF8 and comparative compounds Ref-1 to Ref-3 were also measured in the same manner as compound TADF1. It was confirmed that the amount of Delay luminescence (delayed luminescence) was 5% or more of the amount of Prompt luminescence (immediate luminescence) for compounds TADF1 to TADF8 and comparative compounds Ref-1 to Ref-3. Specifically, for compounds TADF1 to TADF8 and comparative compounds Ref-1 to Ref-3, X Ｄ / X Ｐ The value was 0.05 or more.

[0541] (Fluorescence emission maximum peak wavelength λ ＦＬ and emission spectrum half width FWHM) The compound to be measured was dissolved in toluene, and －６ The resulting solution was placed in a quartz cell (optical path length 1.0 cm), and the maximum peak wavelength λ of fluorescence emission when excited at 400 nm was measured using a fluorescence spectrum measuring device "Spectrofluorometer FP-8300" (manufactured by JASCO Corporation). ＦＬ The maximum peak wavelength λ of compound BD-1 was measured. ＦＬ The wavelength was 455 nm, and the full width at half maximum (FWHM) of the emission spectrum was 23 nm.

[0542] <Synthesis Example> 1. Synthesis of Compound TADF1 (1) Synthesis of Compound (1-2)

[0543]

[0544] Under an argon atmosphere, compound (1-1) (4.50 g, 13.9 mmol), bis(pinacolato)diboron (3.89 g, 15.3 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.204 g, 0.278 mmol), potassium acetate (2.05 g, 20.9 mmol), and 1,4-dioxane (50 mL) were added and heated with stirring at 90°C for 20 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (2.99 g, yield 58%). The obtained solid was the target compound (1-2), and as a result of mass spectrometry analysis, it was found that m / e = 370 for a molecular weight of 370.

[0545] (2) Synthesis of compound TADF1

[0546]

[0547] Under an argon atmosphere, compound (1-2) (2.50 g, 6.75 mmol), compound (1-3) (2.74 g, 6.14 mmol), tetrakistriphenylphosphine palladium (0.213 g, 0.184 mmol), 2 M aqueous sodium carbonate solution (10 mL), and 1,4-dioxane (60 mL) were added and heated with stirring at 90°C for 16 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (3.00 g, yield 75%). The obtained solid was the target compound TADF1, and as a result of mass spectrometry analysis, it was found that m / e = 653 for a molecular weight of 653.

[0548] 2. Synthesis of Compound TADF2 (1) Synthesis of Compound (2-2)

[0549]

[0550] Under an argon atmosphere, compound (2-1) (4.65 g, 14.4 mmol), bis(pinacolato)diboron (4.02 g, 15.8 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.210 g, 0.288 mmol), potassium acetate (2.12 g, 21.6 mmol), and 1,4-dioxane (50 mL) were added and heated with stirring at 90°C for 18 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (3.46 g, yield 65%). The obtained solid was the target compound (2-2), and as a result of mass spectrometry analysis, it was found that the m / e was 370 for a molecular weight of 370.

[0551] (2) Synthesis of compound TADF2

[0552]

[0553] Under an argon atmosphere, compound (2-2) (3.20 g, 8.64 mmol), compound (1-3) (3.50 g, 7.86 mmol), tetrakistriphenylphosphine palladium (0.272 g, 0.236 mmol), 2 M aqueous sodium carbonate solution (13 mL), and 1,4-dioxane (80 mL) were added and heated with stirring at 90°C for 19 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (4.06 g, yield 79%). The obtained solid was the target compound TADF2, and as a result of mass spectrometry analysis, it was found that the m / e was 653 with a molecular weight of 653.

[0554] 3. Synthesis of Compound TADF3 (1) Synthesis of Compound (3-2)

[0555]

[0556] Under an argon atmosphere, compound (3-1) (5.20 g, 16.1 mmol), bis(pinacolato)diboron (4.49 g, 17.7 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.235 g, 0.322 mmol), potassium acetate (2.37 g, 24.1 mmol), and 1,4-dioxane (55 mL) were added and heated with stirring at 90°C for 20 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (3.93 g, yield 66%). The obtained solid was the target compound (3-2), and as a result of mass spectrometry analysis, it was found that the m / e was 370 for a molecular weight of 370.

[0557] (2) Synthesis of compound TADF3

[0558]

[0559] Under an argon atmosphere, compound (3-2) (3.50 g, 9.45 mmol), compound (1-3) (3.83 g, 8.59 mmol), tetrakistriphenylphosphine palladium (0.298 g, 0.258 mmol), 2 M aqueous sodium carbonate solution (14 mL), and 1,4-dioxane (85 mL) were added and heated with stirring at 90°C for 18 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (4.66 g, yield 83%). The obtained solid was the target compound TADF3, and as a result of mass spectrometry analysis, it was found that the m / e was 653 for a molecular weight of 653.

[0560] 4. Synthesis of Compound TADF4 (1) Synthesis of Compound (4-2)

[0561]

[0562] Under an argon atmosphere, 1-bromo-2,3-difluorobenzene (5.35 g, 27.7 mmol), compound (4-1) (10.3 g, 61.0 mmol), cesium carbonate (22.6 g, 69.3 mmol), and N,N-dimethylformamide (200 mL) were added and heated with stirring at 150°C for 10 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (8.55 g, yield 63%). The obtained solid was the target compound (4-2), and as a result of mass spectrometry analysis, it was found that the m / e was 489 with a molecular weight of 489.

[0563] (2) Synthesis of compound (4-3)

[0564]

[0565] Under an argon atmosphere, compound (4-2) (4.60 g, 9.40 mmol), bis(pinacolato)diboron (2.63 g, 10.3 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.137 g, 0.188 mmol), potassium acetate (1.38 g, 14.1 mmol), and 1,4-dioxane (30 mL) were added and heated with stirring at 90°C for 24 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (3.08 g, yield 61%). The obtained solid was the target compound (4-3), and as a result of mass spectrometry analysis, it was found that the m / e was 536 for a molecular weight of 536.

[0566] (3) Synthesis of compound TADF4

[0567]

[0568] Under an argon atmosphere, compound (4-3) (2.75 g, 5.13 mmol), compound (1-3) (2.08 g, 4.66 mmol), tetrakistriphenylphosphine palladium (0.162 g, 0.140 mmol), 2 M aqueous sodium carbonate solution (7 mL), and 1,4-dioxane (45 mL) were added and heated with stirring at 90°C for 20 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (2.94 g, yield 77%). The obtained solid was the target compound TADF4, and as a result of mass spectrometry analysis, it was found that the m / e was 819 for a molecular weight of 819.

[0569] 5. Synthesis of Compound TADF5 (1) Synthesis of Compound (5-2)

[0570]

[0571] Under an argon atmosphere, 1-bromo-2,3-difluorobenzene (4.97 g, 25.8 mmol), compound (5-1) (9.53 g, 56.7 mmol), cesium carbonate (21.0 g, 64.4 mmol), and N,N-dimethylformamide (200 mL) were added and heated with stirring at 150°C for 12 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (7.31 g, yield 58%). The obtained solid was the target compound (5-2), and as a result of mass spectrometry analysis, it was found that the m / e was 489 with a molecular weight of 489.

[0572] (2) Synthesis of compound (5-3)

[0573]

[0574] Under an argon atmosphere, compound (5-2) (3.93 g, 8.03 mmol), bis(pinacolato)diboron (2.24 g, 8.83 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.117 g, 0.161 mmol), potassium acetate (1.18 g, 12.1 mmol), and 1,4-dioxane (25 mL) were added and heated with stirring at 90°C for 21 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (2.46 g, yield 57%). The obtained solid was the target compound (5-3), and as a result of mass spectrometry analysis, it was found that the m / e was 819 for a molecular weight of 819.

[0575] (3) Synthesis of compound TADF5

[0576]

[0577] Under an argon atmosphere, compound (5-3) (2.13 g, 3.97 mmol), compound (1-3) (1.61 g, 3.61 mmol), tetrakistriphenylphosphine palladium (0.125 g, 0.108 mmol), 2 M aqueous sodium carbonate solution (6 mL), and 1,4-dioxane (36 mL) were added and heated with stirring at 90°C for 19 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (2.04 g, yield 69%). The obtained solid was the target compound TADF5, and as a result of mass spectrometry analysis, it was found that the m / e was 819 for a molecular weight of 819.

[0578] 6. Synthesis of Compound TADF6 (1) Synthesis of Compound TADF6

[0579]

[0580] Under an argon atmosphere, compound (1-2) (2.80 g, 7.56 mmol), compound (6-1) (3.06 g, 6.87 mmol), tetrakistriphenylphosphine palladium (0.238 g, 0.206 mmol), 2 M aqueous sodium carbonate solution (11 mL), and 1,4-dioxane (70 mL) were added and heated with stirring at 90°C for 15 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (3.72 g, yield 83%). The obtained solid was the target compound TADF6, and as a result of mass spectrometry analysis, it was found that the m / e was 652 with a molecular weight of 652.

[0581] 7. Synthesis of Compound TADF7 (1) Synthesis of Compound TADF7

[0582]

[0583] Under an argon atmosphere, compound (1-2) (2.63 g, 7.10 mmol), compound (7-1) (2.87 g, 6.46 mmol), tetrakistriphenylphosphine palladium (0.224 g, 0.194 mmol), 2 M aqueous sodium carbonate solution (11 mL), and 1,4-dioxane (65 mL) were added and heated with stirring at 90°C for 17 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (3.29 g, yield 78%). The obtained solid was the target compound TADF7, and as a result of mass spectrometry analysis, it was found that the m / e was 652 with a molecular weight of 652.

[0584] 8. Synthesis of Compound TADF8 (1) Synthesis of Compound (8-2)

[0585]

[0586] Under an argon atmosphere, 1-bromo-2-fluorobenzene (5.86 g, 33.7 mmol), compound (8-1) (12.98 g, 74.1 mmol), cesium carbonate (27.4 g, 84.2 mmol), and N,N-dimethylformamide (220 mL) were added, and the mixture was heated and stirred at 150°C for 13 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (7.65 g, yield 69%). The obtained solid was the target compound (8-2), and as a result of mass spectrometry analysis, it was found that the m / e was 329 with a molecular weight of 329.

[0587] (2) Synthesis of compound (8-3)

[0588]

[0589] Under an argon atmosphere, compound (8-2) (4.11 g, 12.5 mmol), bis(pinacolato)diboron (3.49 g, 13.7 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.183 g, 0.250 mmol), potassium acetate (1.84 g, 18.7 mmol), and 1,4-dioxane (40 mL) were added and heated with stirring at 90°C for 22 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture, the organic layer was extracted, and the solvent was distilled off to obtain a crude product, which was purified by column chromatography to obtain a white solid (2.64 g, yield 56%). The obtained solid was the target compound (8-3), and mass spectrometry analysis showed that the m / e was 377 for a molecular weight of 377.

[0590] (3) Synthesis of compound TADF8

[0591]

[0592] Under an argon atmosphere, compound (8-3) (1.95 g, 5.17 mmol), compound (8-4) (2.17 g, 4.70 mmol), tetrakistriphenylphosphine palladium (0.163 g, 0.141 mmol), 2 M aqueous sodium carbonate solution (8 mL), and 1,4-dioxane (50 mL) were added and heated with stirring at 90°C for 19 hours. After completion of the reaction, the reaction mixture was filtered and washed with water and methanol to obtain a crude product. The obtained crude product was purified by column chromatography to obtain a white solid (2.35 g, yield 74%). The obtained solid was the target compound TADF8, and as a result of mass spectrometry analysis, it was found that m / e = 676 for a molecular weight of 676.

[0593] 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 light-emitting device comprising: a cathode; an anode; and a light-emitting layer disposed between the cathode and the anode, the light-emitting layer containing a compound M2 represented by the following general formula (1), the lowest excited singlet energy S of the compound M2 being: １ (M2) and the energy gap T at 77[K] ７７Ｋ An organic electroluminescence element, wherein a difference ΔST(M2) between the first and second potentials (M2) satisfies the relationship of the following formula (Formula 1). ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV...(Math. 1) (In the general formula (1), X １ ~X ４ are each independently a nitrogen atom or CRx, １ ~X ４ At least one of Rx is a nitrogen atom; when a plurality of Rx's are present, the plurality of Rx's are the same or different; １ ~Y ３ are each independently a nitrogen atom or CH, with the proviso that Y １ ~Y ３ two or more of the rings A, B, C, D and E are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 60 ring atoms; Z １ ~Z ３ Each independently represents a single bond, C(R １ ) (R ２ ), N.R. ３ , an oxygen atom, or a sulfur atom; Z １ , Z ２ and Z ３ are the same or different, Ar １ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), m represents 1, 2, 3, 4, or 5, n represents 0, 1, 2, 3, or 4, m+n=5, and when m represents 2, 3, 4, or 5, a plurality of X １ are the same or different from each other, and a plurality of X ２ are the same or different from each other, and a plurality of X ３ are the same or different from each other, and a plurality of X ４ are the same or different from each other; a plurality of A rings are the same or different from each other; a plurality of Z １ are the same or different from each other, and when n is 2, 3 or 4, a plurality of Ar １ are the same or different, *1 and *2 each represent a bonding position to a benzene ring, and in the general formula (2), Z is C(R １Ａ ) (R ２Ａ ), N.R. ３Ａ , an oxygen atom, or a sulfur atom; R １１ ~R １８ one or more pairs of adjacent two or more of the groups are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, with the proviso that Ar １ is a group represented by the general formula (2), R １１ ~R １８ and R ３Ａ one of R and R is a single bond to the benzene ring in the general formula (1); １ , R ２ , R ３ , R １Ａ , R ２Ａ and R which is not a single bond to the benzene ring, does not form the substituted or unsubstituted monocycle, and does not form the substituted or unsubstituted fused ring. ３Ａ and R １１ ~R １８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ ) group, -S-(R ９０５ ), a group represented by -N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７ each independently represents 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 When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other, R ９０５ When there are multiple R ９０５ are the same or different from each other, R ９０６ When there are multiple R ９０６ are the same or different from each other, R ９０７ When there are multiple R ９０７ are the same or different from each other.) 2. Z １ , Z ２ and Z ３ The organic electroluminescence device according to claim 1 , wherein:

3. The organic electroluminescence element according to claim 1 or 2, wherein ring A, ring B, ring C, ring D and ring E are each independently a substituted or unsubstituted benzene ring, or a substituted or unsubstituted dibenzothiophene ring.

4. X １ ~X ３ is a nitrogen atom, and X is not a nitrogen atom. １ ~X ４ The organic electroluminescence device according to claim 1 , wherein: is CRx.

5. X ２ Or X ４ is a nitrogen atom, and X is not a nitrogen atom １ ~X ４ The organic electroluminescence device according to claim 1 , wherein:

6. Y ２ and Y ３ are nitrogen atoms, and Y １ is CH, or Y １ ~Y ３ The organic electroluminescence device according to claim 1 , wherein three of the above are nitrogen atoms.

7. Y １ ~Y ３ The organic electroluminescence device according to claim 1 , wherein three of the above are nitrogen atoms.

8. Ar １ The organic electroluminescence device according to claim 1 , wherein is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

9. The organic electroluminescence device according to any one of claims 1 to 8, wherein in the compound M2, the partial structures represented by the following general formula (1A) are each independently a group represented by any one of the following general formulas (11A) to (14A). (In the above general formula (1A), ring A, X １ ~X ４ and Z １ respectively represent the A ring and X in the general formula (1). １ ~X ４ and Z １ When a plurality of partial structures represented by the general formula (1A) are present, the plurality of partial structures represented by the general formula (1A) are the same or different from each other, and *1 has the same meaning as *1 in the general formula (1). (In the above general formulae (11A) to (14A), R ３１１ ~R ３１８ 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. ３１１ ~R ３１８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ ) group, -S-(R ９０５ ), a group represented by -N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are R in the general formula (1), ９０１ ~R ９０７ *1 has the same meaning as *1 in the general formula (1A).

10. The organic electroluminescence device according to any one of claims 1 to 9, wherein in compound M2, the partial structure represented by the following general formula (1B) and the partial structure represented by the following general formula (1C) are each independently a group represented by any one of the following general formulas (11B) to (13B), and the partial structure represented by the following general formula (1B) and the partial structure represented by the following general formula (1C) are the same or different from each other. (In the general formulae (1B) and (1C), ring B, ring C, ring D, ring E, ring Z ２ and Z ３ respectively represent ring B, ring C, ring D, ring E, and Z in the general formula (1). ２ and Z ３ and *3 represents the Y １ and Y ３ and *4 indicates the bonding position to the carbon atom between Y ２ and Y ３ This indicates the bond position to the carbon atom between (In the above general formulae (11B) to (13B), R ５１１ ~R ５１４ and R ５２０ 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 condensed ring, or are not bonded to each other, ６１１ ~R ６１４ and R ６２０ 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 condensed ring, or are not bonded to each other and a plurality of R ５２０ are the same or different from each other, and a plurality of R ６２０ are the same or different, Ar ３ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R not forming a substituted or unsubstituted monocycle and not forming a substituted or unsubstituted fused ring ５１１ ~R ５１４ , R ５２０ , R ６１１ ~R ６１４ and R ６２０ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ ) group, -S-(R ９０５ ), a group represented by -N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ９０１ ~R ９０７ are R in the general formula (1), ９０１ ~R ９０７ *5 has the same meaning as *3 in the general formula (1B) or *4 in the general formula (1C).

11. The organic electroluminescence device according to any one of claims 1 to 10, wherein m is 1.

12. Rx, R １ , R ２ , R ３ , R １Ａ , R ２Ａ , R ３Ａ and R １１ ~R １８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

13. The organic electroluminescence device according to any one of claims 1 to 12, wherein the light-emitting layer contains the compound M2 as a sensitizing material.

14. The organic electroluminescence device according to claim 13, wherein the sensitizing material is a delayed fluorescent compound.

15. The organic electroluminescence element according to any one of claims 1 to 14, wherein the light-emitting layer further contains a fluorescent material, and the fluorescent material is a compound represented by the following general formula (41): (In the general formula (41), ring a, ring b and ring c are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms; L ４０１ and L ４０２ each independently represents O, S, Se, or NR ４０ , C(R ４１ ) (R ４２ ), or Si(R ４３ ) (R ４４ ) and L ４０３ is B, P, or P=O; R ４０ ~R ４４ each independently represents: bonding to the ring a, ring b, or ring c to form a substituted or unsubstituted monocycle; bonding to the ring a, ring b, or ring c to form a substituted or unsubstituted fused ring; or not bonding to the ring a, ring b, or ring c, ４１ and R ４２ 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, R ４３ and R ４４ 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, do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ４０ ~R ４４ each independently represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -CR ４５ an iminyl group represented by N=N, 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, ４５ is a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, R ４０ When there are multiple R ４０ are the same or different from each other, R ４１ When there are multiple R ４１ are the same or different from each other, R ４２ When there are multiple R ４２ are the same or different from each other, R ４３ When there are multiple R ４３ are the same or different from each other, R ４４ When there are multiple R ４４ are the same or different from each other, R ４５ When there are multiple R ４５ are the same or different from each other.) 16. The organic electroluminescence device according to any one of claims 1 to 12, wherein the light-emitting layer contains the compound M2 as a host material.

17. The organic electroluminescence device according to claim 16, wherein the host material is a delayed fluorescent compound.

18. The organic electroluminescence device according to any one of claims 1 to 17, wherein the light-emitting layer does not contain a metal complex.

19. The organic electroluminescence device according to any one of claims 1 to 18, wherein the light-emitting layer does not contain a phosphorescent material.

20. The organic electroluminescence device according to any one of claims 1 to 19, further comprising a hole transport layer between the anode and the light emitting layer.

21. The organic electroluminescence device according to any one of claims 1 to 20, further comprising an electron transport layer between the cathode and the light-emitting layer.

22. An electronic device equipped with the organic electroluminescence element according to any one of claims 1 to 21.

23. A compound represented by the following general formula (100): (In the above general formula (100), Ar １００ is a group represented by the following general formula (1A), １００ When a plurality of Ar are present, a plurality of Ar １００ are the same or different, Y １ ~Y ３ are each independently a nitrogen atom or CH, with the proviso that Y １ ~Y ３ two or more of the rings B, C, D and E are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 60 ring atoms; ２ and Z ３ Each independently represents a single bond, C(R １ ) (R ２ ), N.R. ３ , an oxygen atom, or a sulfur atom; Z ２ and Z ３ are the same or different, Ar １ represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), m represents 1, 2, 3, 4, or 5, n represents 0, 1, 2, 3, or 4, m+n=5, and when n represents 2, 3, or 4, a plurality of Ar １ are the same or different, *1 and *2 each represent a bonding position to a benzene ring, and in the general formula (2), Z is C(R １Ａ ) (R ２Ａ ), N.R. ３Ａ , an oxygen atom, or a sulfur atom; R １１ ~R １８ one or more pairs of adjacent two or more of the groups are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, with the proviso that Ar １ is a group represented by the general formula (2), R １１ ~R １８ and R ３Ａ is a single bond to the benzene ring in the general formula (100), １ , R ２ , R ３ , R １Ａ , R ２Ａ and R which is not a single bond to the benzene ring, does not form the substituted or unsubstituted monocycle, and does not form the substituted or unsubstituted fused ring. ３Ａ , and R １１ ~R １８ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) group represented by -O-(R ９０４ ) group, -S-(R ９０５ ), a group represented by -N(R ９０６ ) (R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. ９０１ ~R ９０７ each independently represents 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 When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other, R ９０５ When there are multiple R ９０５ are the same or different from each other, R ９０６ When there are multiple R ９０６ are the same or different from each other, R ９０７ When there are multiple R ９０７ are the same or different from each other.) (In the above general formula (1A), Z １ is Z in the general formula (100). ２ X １ ~X ４ are each independently a nitrogen atom or CRx, １ ~X ４ at least one of the rings is a nitrogen atom, the ring A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 60 ring atoms, and Rx is R in the general formula (2). １１ ~R １８ and when a plurality of A rings are present, the plurality of A rings are the same as or different from each other. When a plurality of Rx's are present, the plurality of Rx's are the same as or different from each other. When a plurality of groups represented by the general formula (1A) are present, the plurality of groups represented by the general formula (1A) are the same as or different from each other. *1 indicates the bonding position with the benzene ring in the general formula (100).) (However, Y １ ~Y ３ are nitrogen atoms, and in the general formula (100), at least one Ar １００ is a group represented by any one of the following general formulas (100A), (100B), (100C) and (100D), the general formula (100) satisfies at least one of the following requirements (i), (ii) and (iii). １００ is a group represented by the following general formula (100A), m is 2, 3, 4 or 5, or n is 1, and one Ar １ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), or n is 2 and two Ar １ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), n is 3, and three Ar １ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2), or n is 4, and four Ar １ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (2). １００ is a group represented by the following general formula (100B), (100C) or (100D), at least one group represented by the following general formula (100B), (100C) or (100D) is bonded to the carbon atom at the position a in the general formula (100). １００ is a group represented by the following formula (100B), (100C) or (100D), ring B, ring C, ring D and ring E are each independently an unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or an unsubstituted heterocycle having 5 to 60 ring atoms. (In the above general formulae (100A), (100B), (100C) and (100D), R ３１１ ~R ３１４ 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. ３１１ ~R ３１４ each independently represents R in the general formula (2) １１ ~R １８ and A ring is the same as A ring in the general formula (1A). When a plurality of A rings are present, the plurality of A rings are the same as or different from each other. When a plurality of groups represented by the general formula (100A) are present, the plurality of groups represented by the general formula (100A) are the same as or different from each other. When a plurality of groups represented by the general formula (100B) are present, the plurality of groups represented by the general formula (100B) are the same as or different from each other. When a plurality of groups represented by the general formula (100C) are present, the plurality of groups represented by the general formula (100C) are the same as or different from each other. When a plurality of groups represented by the general formula (100D) are present, the plurality of groups represented by the general formula (100D) are the same as or different from each other. *1 indicates the bonding position with the benzene ring in the general formula (100).

24. Z ２ and Z ３ The compound of claim 23 , wherein:

25. The compound according to claim 23 or 24, wherein, when at least one of the requirements (i) and (ii) is satisfied, ring B, ring C, ring D and ring E are each independently a substituted or unsubstituted benzene ring, or a substituted or unsubstituted dibenzothiophene ring, and when the requirement (iii) is satisfied, ring B, ring C, ring D and ring E are each independently an unsubstituted benzene ring, or an unsubstituted dibenzothiophene ring.

26. X １ ~X ３ is a nitrogen atom, and X is not a nitrogen atom. １ ~X ４ The compound according to any one of claims 23 to 25, wherein: is CRx.

27. X ２ Or X ４ is a nitrogen atom, and X is not a nitrogen atom １ ~X ４ 27. The compound of any one of claims 23 to 26, wherein: is CRx.

28. Y ２ and Y ３ are nitrogen atoms, and Y １ is CH, or Y １ ~Y ３ 28. The compound according to any one of claims 23 to 27, wherein three of are nitrogen atoms.

29. Y １ ~Y ３ 29. The compound according to any one of claims 23 to 28, wherein three of are nitrogen atoms.

30. Ar １ is a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. The compound according to any one of claims 23 to 29, 31. Ar １００ is a group represented by the general formula (100B), (100C) or (100D), m is 1. The compound according to any one of claims 23 to 30, 32. R １ , R ２ , R ３ , R １Ａ , R ２Ａ , R ３Ａ , R １１ ~R １８ and R ３１１ ~R ３１４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

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