Compound, organic-electroluminescence-device material, organic electroluminescence device, and electronic apparatus

Abstract

To provide a compound that enables an organic electroluminescence device to emit light with high efficiency.SOLUTION: Specifically, for example, the following compounds TADF1, TADF2 and TADF3 are illustrated.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic EL elements that use light emitted from singlet excitons are 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 elements, various studies have been conducted on compounds used in organic EL elements (see, for example, Patent Documents 1 and 2). Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] US Patent Application Publication No. 2022 / 0177492 [Patent Document 2] US Patent Application Publication No. 2021 / 0066613 Summary of the Invention [Problem to be solved by the invention]

[0004] In order to improve the performance of electronic devices such as displays, there is a demand for further improvement in the performance of organic EL elements.

[0005] An object of the present invention is to provide a compound capable of making an organic electroluminescence device emit light with high efficiency. Another object of the present invention is to provide a material for an organic electroluminescence device containing the compound. Another object of the present invention is to provide an organic electroluminescence device that emits light with high efficiency, and to provide an electronic device equipped with the organic electroluminescence device. [Means for solving the problem]

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

[0007] [ka]

[0008] [ka]

[0009] (In the general formula (1), X 1 ~X 4 are each independently a nitrogen atom or CRx; However, X 1 ~X 4 At least one of the groups is a nitrogen atom, When a plurality of Rx's are present, the plurality of Rx's are the same or different from each other, Y 1 ~Y 3 are each independently a nitrogen atom or CH; However, Y 1 ~Y 3 At least two of the groups are nitrogen atoms; Ring A, ring B and ring C each independently represent 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 and Z2 are each independently a single bond, C(R 1 )(R 2 ), N.R. 3 , an oxygen atom, or a sulfur atom; Ar 1 teeth, Hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A group represented by the general formula (2), Ar 2 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A group represented by the general formula (3), m is 1, 2, 3, 4 or 5; n is 0, 1, 2, 3 or 4; m+n=5, When m is 2, 3, 4 or 5, Multiple X's 1 are identical or different from each other, Multiple X's 2 are identical or different from each other, Multiple X's 3 are identical or different from each other, Multiple X's 4 are identical or different from each other, The A rings are the same or different from each other, Multiple Zs 1 are identical or different from each other, When n is 2, 3 or 4, Multiple Ar 1 are identical or different from each other, *1 and *2 indicate the bonding positions to the benzene ring, 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 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, Ar 1 is a group represented by the general formula (2), R 11 ~R 18 and R 3A one of them is a single bond to the benzene ring in the general formula (1), In the general formula (3), W is C(R 21A )(R 22A ), an oxygen atom, or a sulfur atom; R 21 ~R 28 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, Ar 2 is a group represented by the general formula (3), R 21 ~R 28 In the general formula (1), one of the following is Y 1 and Y 3 is a single bond to a carbon atom between Rx, R 1 , R 2 , R 3 , R 1A , R 2A , R 21A , R 22A and the Y 1 and Y 3 R is not a single bond to a carbon atom between 3A , R 11 ~R 18 and R 21 ~R 28 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. (In the compound represented by the general formula (1), R 901 ~R 907 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901 are the same or different from each other, R 902 If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are either identical or different.)

[0010] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, which contains a compound according to one aspect of the present invention.

[0011] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising a cathode, an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising a compound according to one aspect of the present invention as compound M2.

[0012] 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. Effect of the Invention

[0013] According to one aspect of the present invention, it is possible to provide a compound that can cause an organic electroluminescence element to emit light with high efficiency. According to one aspect of the present invention, it is possible to provide a material for an organic electroluminescence element that contains the compound. According to one aspect 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. [Brief description of the drawings]

[0014] [Figure 1] 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. [Diagram 2]FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Diagram 3] FIG. 13 is a diagram showing an example of an attenuation curve of a transient PL. [Figure 4] FIG. 2 is a diagram showing the energy levels of a sensitizing material and a fluorescent material in an emission layer of an example of an organic electroluminescence element according to a first embodiment of the present invention, and the relationship of energy transfer. [Diagram 5] FIG. 4 is a diagram showing the energy levels and energy transfer relationship of a second host material, a sensitizing material, and a fluorescent material in an example of an emitting layer of an organic electroluminescence device according to a second embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] [Definition] In this specification, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

[0016] In the present specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0017] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, the number of ring carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms of a 9,9'-spirobifluorenyl group is 25. In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0018] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, and a ring assembly). The number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. For example, hydrogen atoms bonded to carbon atoms of a quinazoline ring or atoms constituting a substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

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

[0020] In the present specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having the number of atoms XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0021] In this specification, the term "unsubstituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and the term "substituted ZZ group" refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In the present specification, "unsubstituted" in the case of "a substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. In the present specification, "substituted" in the case of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the case of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0022] "Substituents Described Herein" The substituents described in this specification will be described below.

[0023] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms, unless otherwise specified in this specification. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0024] "Substituted or unsubstituted aryl groups" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, when the term "aryl group" is simply used, it includes both an "unsubstituted aryl group" and a "substituted aryl group". The term "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include the "unsubstituted aryl group" in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom bonded to a carbon atom of the aryl group itself is further replaced with a substituent, and the "substituted aryl group" in the specific example group G1B below in which a hydrogen atom of a substituent is further replaced with a substituent.

[0025] Unsubstituted aryl groups (specific example group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, Benzanthryl group, A phenanthryl group, Benzophenanthryl group, A phenalenyl group, Pyrenyl group, Chrysenyl group, benzochrysenyl group, A triphenylenyl group, Benzotriphenylenyl group, tetracenyl group, Pentacenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, fluoranthenyl group, Benzofluoranthenyl group, Perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0026] [ka]

[0027] [ka]

[0028] Substituted aryl groups (specific example group G1B): o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0029] "Substituted or unsubstituted heterocyclic groups" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when the term "heterocyclic group" is simply used, it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". The term "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes the groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent, and the groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" in the specific example group G2B are further replaced with a substituent.

[0030] The specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0031] Specific example group G2B includes, for example, the following nitrogen atom-containing substituted heterocyclic groups (specific example group G2B1), oxygen atom-containing substituted heterocyclic groups (specific example group G2B2), sulfur atom-containing substituted heterocyclic groups (specific example group G2B3), and monovalent heterocyclic groups derived from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33), in which one or more hydrogen atoms are replaced with substituents (specific example group G2B4).

[0032] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, imidazolyl group, A pyrazolyl group, A triazolyl group, Tetrazolyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Pyridyl group, pyridazinyl group, pyrimidinyl group, A pyrazinyl group, Triazinyl group, Indolyl groups, isoindolyl group, Indolizinyl group, A quinolizinyl group, A quinolyl group, isoquinolyl group, Cinnolyl group, phthalazinyl group, A quinazolinyl group, A quinoxalinyl group, Benzimidazolyl group, Indazolyl group, A phenanthrolinyl group, A phenanthridinyl group, acridinyl group, A phenazinyl group, A carbazolyl group, Benzocarbazolyl group, morpholino group, phenoxazinyl group, A phenothiazinyl group, Azacarbazolyl and diazacarbazolyl groups.

[0033] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): Furyl group, oxazolyl group, an isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, Dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, phenoxazinyl group, morpholino group, Dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, Azanaphthobenzofuranyl groups, and Diazanaphthobenzofuranyl group.

[0034] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): A thienyl group, A thiazolyl group, isothiazolyl group, A thiadiazolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, Benzisothiazolyl group, A phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0035] 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):

[0036] [ka]

[0037] [ka]

[0038] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0039] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): A (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, Ethyl benzimidazolyl group, phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0040] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0041] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): Phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0042] 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):

[0043] The above-mentioned "one or more hydrogen atoms of a 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 the above is NH, and X A and Y A or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

[0044] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when the term "alkyl group" is simply mentioned, it includes both the "unsubstituted alkyl group" and the "substituted alkyl group". The term "substituted alkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent.

[0045] Unsubstituted alkyl groups (specific example group G3A): Methyl group, Ethyl group, n-propyl group, isopropyl group, n-Butyl group, isobutyl group, s-Butyl group, and t-Butyl group.

[0046] Substituted alkyl groups (specific example group G3B): Heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0047] "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group". The term "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and examples of substituted alkenyl groups (specific example group G4B). The examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent.

[0048] Unsubstituted alkenyl groups (specific example group G4A): Vinyl group, Allyl groups, 1-butenyl group, 2-butenyl group, and 3-Butenyl group.

[0049] Substituted alkenyl groups (specific example group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-Dimethylallyl group.

[0050] "Substituted or unsubstituted alkynyl groups" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group".) Hereinafter, when simply referring to an "alkynyl group", it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group". The term "substituted alkynyl group" refers to an "unsubstituted alkynyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include the following "unsubstituted alkynyl groups" (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.

[0051] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group.

[0052] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group". The term "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" in the specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself are replaced with a substituent, and a group in the "substituted cycloalkyl group" in the specific example group G6B in which a hydrogen atom of a substituent is further replaced with a substituent.

[0053] Unsubstituted cycloalkyl groups (specific example group G6A): A cyclopropyl group, A cyclobutyl group, Cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-Norbornyl group.

[0054] Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl group.

[0055] -Si(R 901 )(R 902 )(R 903 ) a group represented by As described herein, -Si(R 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0056] -O-(R 904 ) a group represented by As described herein, -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0057] -S-(R 905 ) a group represented by As described herein, -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0058] -N(R 906 )(R 907 ) a group represented by As described herein, -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: Where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6. -The multiple G1's in N(G1)(G1) are the same or different from each other. -The multiple G2's in N(G2)(G2) are the same or different from each other. -The multiple G3's in N(G3)(G3) are the same or different from each other. The multiple G6s in -N(G6)(G6) are the same or different from each other.

[0059] "Halogen atoms" Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0060] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a fluorine atom.

[0061] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms in the substituent in the "substituted haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

[0062] "Substituted or unsubstituted alkoxy groups" A specific example of the "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0063] "Substituted or unsubstituted alkylthio groups" A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0064] "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0065] "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0066] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are the same or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0067] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, the "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one aspect of a "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in the present specification. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0068] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, and the like.

[0069] The substituted or unsubstituted heterocyclic group described in the present specification, unless otherwise specified in the present specification, is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

[0070] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in the specification.

[0071] [ka]

[0072] In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise specified in the specification.

[0073] [ka]

[0074] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0075] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0076] [ka]

[0077] In the above general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0078] The substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like, unless otherwise specified herein.

[0079] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0080] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0081] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

[0082] The substituted or unsubstituted arylene group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0083] [ka]

[0084] [ka]

[0085] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the above general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0086] [ka]

[0087] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the above general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0088] [ka]

[0089] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the above general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0090] The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the groups represented by the following general formulae (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

[0100] The above is an explanation of "the substituents described in this specification".

[0101] - "When bonded to form a ring" In this specification, the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", and the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other". In this specification, the cases where "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more of a set of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "a case where they are bonded to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the mother skeleton is an anthracene ring, will be explained as an example.

[0102] [ka]

[0103] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 With R 922 and R 923 With R 923 and R 924 With R 924 and R 930 With R 930 and R 925 With R 925 and R 926 With R 926 and R 927 With R 927 and R 928 With R 928 and R 929 and R 929 and R 921 It is paired with .

[0104] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to ring Q A At the same time, R 925 and R 926 and are bonded to ring Q B When the above general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0105] [ka]

[0106] The case where a "set of two or more adjacent units" forms a ring includes not only the case where a set of two adjacent units is bonded as in the previous example, but also the case where a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to ring Q A and R 922 and R923 and are bonded to ring Q C The three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), the ring Q A and Ring Q C is R 922 Share.

[0107] [ka]

[0108] The "monocyclic ring" or "condensed ring" formed may be a saturated or unsaturated ring as the structure of only the ring formed. Even when "one of the pairs of adjacent two" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or the "condensed ring" may form a saturated or unsaturated ring. For example, the ring Q formed in the general formula (TEMP-104) may be a saturated or unsaturated ring. A and Ring Q B are "monocyclic" or "condensed rings". In addition, the ring Q formed in the general formula (TEMP-105) A , and ring Q C is a "fused ring". The ring Q in the above general formula (TEMP-105) A and Kan Q C That is, Ring Q A and Kan Q C The ring Q in the general formula (TMEP-104) is condensed to form a condensed ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0109] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G1 are terminated with a hydrogen atom. Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "form a ring" means that a ring is formed only with a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more optional elements. For example, R 921 and R 922 and are bonded together to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When the carbon atom of the anthracene skeleton to which R is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 and R 922 The ring formed by this is a benzene ring.

[0110] Here, unless otherwise specified in the present specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of a carbon element or a nitrogen element), 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 an arbitrary element other than a carbon element is included, the ring formed is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting a single ring or a condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified in this specification, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring. When "one or more of a set of two or more adjacent rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more of a set of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

[0111] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned section "Substituents described in this specification". When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification". The above is an explanation of the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring" ("combined to form a ring").

[0112] Substituents in the phrase "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and a group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms, Here, R 901 ~R 907 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It 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 901 If there are two or more, there are two or more R 901 are identical or different from each other, R 902 If there are two or more, there are two or more R 902 are identical or different from each other, R 903 If there are two or more, there are two or more R903 are identical or different from each other, R 904 If there are two or more, there are two or more R 904 are identical or different from each other, R 905 If there are two or more, there are two or more R 905 are identical or different from each other, R 906 If there are two or more, there are two or more R 906 are identical or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0113] In one embodiment, the substituent in the above "substituted or unsubstituted" is: an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms, and The group is selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

[0114] In one embodiment, the substituent in the above "substituted or unsubstituted" is: an alkyl group having 1 to 18 carbon atoms; An aryl group having 6 to 18 ring carbon atoms, and The group is selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

[0115] 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."

[0116] Unless otherwise specified in this specification, any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in the present specification, the optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0117] In this specification, a numerical range expressed using "AA to BB" means a range including the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

[0118] In this specification, a mathematical expression expressed as "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, a mathematical expression expressed as "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.

[0119] First Embodiment <Compound> The compound according to this embodiment is a compound represented by the following general formula (1).

[0120] [ka]

[0121] [ka]

[0122] (In the general formula (1), X 1 ~X 4 are each independently a nitrogen atom or CRx; However, X 1 ~X 4 At least one of the groups is a nitrogen atom, When a plurality of Rx's are present, the plurality of Rx's are the same or different from each other, Y 1 ~Y 3 are each independently a nitrogen atom or CH; However, Y1 ~Y 3 At least two of the groups are nitrogen atoms; Ring A, ring B and ring C each independently represent 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 and Z 2 are each independently a single bond, C(R 1 )(R 2 ), N.R. 3 , an oxygen atom, or a sulfur atom; Ar 1 teeth, Hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A group represented by the general formula (2), Ar 2 teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A group represented by the general formula (3), m is 1, 2, 3, 4 or 5; n is 0, 1, 2, 3 or 4; m+n=5, When m is 2, 3, 4 or 5, Multiple X's 1 are identical or different from each other, Multiple X's 2 are identical or different from each other, Multiple X's 3 are identical or different from each other, Multiple X's 4 are identical or different from each other, The A rings are the same or different from each other, Multiple Zs 1 are identical or different from each other, When n is 2, 3 or 4, Multiple Ar 1 are identical or different from each other, *1 and *2 indicate the bonding positions to the benzene ring, 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 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, Ar 1 is a group represented by the general formula (2), R 11 ~R 18 and R 3A one of them is a single bond to the benzene ring in the general formula (1), In the general formula (3), W is C(R 21A )(R 22A ), an oxygen atom, or a sulfur atom; R 21 ~R 28 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, Ar 2 is a group represented by the general formula (3), R 21 ~R 28 In the general formula (1), one of the following is Y 1 and Y 3 is a single bond to a carbon atom between Rx, R 1 , R 2 , R 3 , R 1A , R 2A , R 21A , R 22A and the Y 1and Y 3 R is not a single bond to a carbon atom between 3A , R 11 ~R 18 and R 21 ~R 28 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. (In the compound represented by the general formula (1), R 901 ~R 907 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 If there are multiple R 901are 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 either identical or different.)

[0123] The compound of this embodiment (the compound represented by the general formula (1)) has a structure in which at least (i) an azine ring having a donor group such as a carbazolyl group, and (ii) a donor group containing a nitrogen-containing 6-membered ring structure such as an azacarbazolyl group are bonded to a benzene ring. The compound of this embodiment has the above (i) and (ii), and thereby has the following effects. In the compound of this embodiment, the azacarbazolyl group as a donor group containing a nitrogen-containing six-membered ring structure has a weaker electron donating property but a higher minimum excited triplet energy than a carbazolyl group not containing a nitrogen-containing six-membered ring structure. Therefore, by using the compound of this embodiment, it is possible to achieve a maximum fluorescence emission peak wavelength λ while maintaining the TADF property. FL (PL peak) can be shifted to a shorter wavelength. In addition, by using the compound of this embodiment, the maximum fluorescent emission peak wavelength λ FL The wavelength of light emitted from the organic EL element is shortened, improving the blue chromaticity of the element. As a result, the BI (Blue Index), which is an index of luminous efficiency that also takes chromaticity into account, can be improved. In this specification, the value of "L / J / CIEy" is referred to as the blue index (BI). The chromaticity CIEy and the current efficiency L / J (unit: cd / A) are calculated by the method described in the Examples.

[0124] For example, the following compound TADF1 has a structure in which an azine ring having a 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 Ref-1 is a compound in which the azacarbazolyl group in the compound TADF1 is replaced with a carbazolyl group. As shown below, compound TADF1 has a longer maximum fluorescence emission peak wavelength λ than compound Ref-1. FL It can be seen that the wavelength of the maximum fluorescent peak λ FL is measured by the method described in the Examples.

[0125] TIFF2025021083000026.tif65166

[0126] In the compound of this embodiment, Z 1 and Z 2 is preferably a single bond.

[0127] In the compound of this embodiment, it is preferable that ring A, ring B and ring C are each independently a substituted or unsubstituted benzene ring, or a substituted or unsubstituted dibenzothiophene ring. In the compound of this embodiment, it is preferable that both of the B ring and the C ring are substituted or unsubstituted benzene rings, or one of the B ring and the C ring is a substituted or unsubstituted benzene ring and the other is a substituted or unsubstituted dibenzothiophene ring.

[0128] In the compound of this embodiment, X 1 ~X 3 One of the X's is a nitrogen atom, and the other is not a nitrogen atom. 1 ~X 4 is preferably CRx.

[0129] In the compound of this embodiment, X 2 Or X 4 is a nitrogen atom and X is not a nitrogen atom 1 ~X 4 is preferably CRx. In one embodiment of the compound, X 1 is a nitrogen atom, and X 2 ~X 4 In one embodiment of the compound, X 2 is a nitrogen atom, and X 1 , X 3 and X 4 In one embodiment of the compound, X 3 is a nitrogen atom, and X 1 , X 2 and X 4 In one embodiment of the compound, X 4 is a nitrogen atom, and X 1 , X 2 and X 3 is CRx.

[0130] In the compound of this embodiment, Y 2 and Y 3 are nitrogen atoms, and Y 1 is CH or Y 1 ~Y 3 It is preferable that three of the above are nitrogen atoms.

[0131] In the compound of this embodiment, Y 1 ~Y 3 It is preferable that three of the above are nitrogen atoms.

[0132] In the compound of this embodiment, Ar 1 is preferably a hydrogen atom, or 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.

[0133] In the compound of this embodiment, Ar 2is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0134] In the compound of this embodiment, in the compound represented by the general formula (1), the partial structures represented by the following general formula (1A) are preferably each independently a group represented by any one of the following general formulae (11A) to (14A). When the compound represented by the general formula (1) contains 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 or different from each other.

[0135] [ka]

[0136] (In the above 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 1 is synonymous with 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) may be the same or different, and *1 has the same meaning as *1 in the general formula (1).

[0137] [ka]

[0138] (In the general formulae (11A) to (14A), R 311 ~R 318 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 311 ~R 318 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R in the general formulae (11A) to (14A) 901 ~R 907 are R in the general formula (1), 901 ~R 907 is synonymous with *1 has the same meaning as *1 in the general formula (1A).

[0139] In the general formulae (11A) to (14A), R 311 ~R 318 It is preferable that any pair of adjacent two or more of the above is not bonded to each other.

[0140] In the compound of the present embodiment, in the compound represented by the general formula (1), it is also preferable that the partial structures represented by the general formula (1A) are each independently a group represented by any one of the following general formulae (15A) to (18A).

[0141] [ka]

[0142] (In the general formulae (15A) to (18A), The A1 ring is a ring structure represented by the following general formula (19A): The A2 ring is a ring structure represented by the following general formula (20A): Ring A1 and ring A2 are fused to the adjacent ring at any position; R 311 ~R 314 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 411 ~R 414 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formulae (15A) to (18A), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed 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 is synonymous with *1 has the same meaning as *1 in the general formula (1A).

[0143] [ka]

[0144] (In the general formula (19A), Multiple R 415 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. 415 R in the general formulae (11A) to (14A) does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 311 ~R 318 is synonymous with Multiple R 415 are the same or different, 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 equivalent to

[0145] In the general formulae (15A) to (18A), R 311 ~R 314 and R 411 ~R 414 It is preferable that any pair of adjacent two or more of the above is not bonded to each other. In the general formula (19A), a plurality of R 415 It is preferred that none of the pairs of In the general formula (19A), 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. In the general formula (20A), Z 12 is preferably a sulfur atom.

[0146] In the compound of this embodiment, in the compound represented by the general formula (1), the partial structure represented by the following general formula (1B) is preferably a group represented by any one of the following general formulae (11B) to (13B).

[0147] [ka]

[0148] (In the general formula (1B), ring B, ring C and Z 2 respectively represent ring B, ring C and Z in the general formula (1). 2 *3 is the same as the Y 2 and Y 3 )

[0149] [ka]

[0150] (In the general formulae (11B) to (13B), R 511 ~R 514 and R 520 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 611 ~R 614 and R 620 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Multiple R 520 are the same or different, Multiple R 620 are the same or different, Ar 3 teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 511 ~R 514 , R 520 , R 611 ~R 614 and R 620 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R in the general formulae (11B) to (13B) 901 ~R 907 are R in the general formula (1), 901 ~R 907 is synonymous with *3 has the same meaning as *3 in the general formula (1B).

[0151] In the compounds of this embodiment, m is preferably 1.

[0152] 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 adjacent two or more of the above is not bonded to each other.

[0153] In this embodiment, in the compound represented by general formula (1), the partial structure represented by general formula (1B) is also preferably a group represented by the following general formula (14B) or (15B).

[0154] [ka]

[0155] (In the general formula (14B), Z 13 is C(R 1C )(R 2C ), an oxygen atom, or a sulfur atom; R 1C and R 2Ceach 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, R 511 ~R 514 , R 520 , R 611 ~R 614 and R 620 are R in the general formula (13B), 511 ~R 514 , R 520 , R 611 ~R 614 and R 620 is synonymous with *5 has the same meaning as *3 in the general formula (1B). (In the general formula (15B), B1 ring, B2 ring, R 311B ~R 314B and R 411B ~R 414B respectively represent the A1 ring, the A2 ring, and R 311 ~R 314 and R 411 ~R 414 and *5 has the same meaning as *3 in the general formula (1B).

[0156] In the general formula (14B), R 511 ~R 514 , R 520 , R 611 ~R 614 and R 620 It is preferable that any pair of adjacent two or more of the above is not bonded to each other. In the general formula (15B), R 311B ~R 314B and R 411B ~R 414B It is preferable that any pair of adjacent two or more of the above is not bonded to each other. In the general formula (15B), Z in the general formula (20A) representing the B2 ring 12 is preferably a sulfur atom.

[0157] 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.

[0158] In this embodiment, the compound represented by the general formula (1) is preferably a compound represented by any one of the following general formulae (110) to (117).

[0159] [ka]

[0160] [ka]

[0161] [ka]

[0162] [ka]

[0163] (In the general formulae (110) to (113), R 311 ~R 318 R in the general formulae (11A) to (14A) 311 ~R 318 is synonymous with Y 1 ~Y 3 , Ar 1 , Ar 2 , m and n are each the Y 1 ~Y 3 , Ar 1 , Ar 2 , m and n are synonymous therewith; *1 and *2 are the same as *1 and *2 in the general formula (1), respectively. R 511 ~R514 and R 520 are R in the general formula (11B), 511 ~R 514 and R 520 is equivalent to

[0164] [ka]

[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168] (In the general formulae (114) to (117), the ring A1, the ring A2, R 311 ~R 314 and R 411 ~R 414 respectively represent the A1 ring, the A2 ring, and R in the general formulae (15A) to (18A). 311 ~R 314 and R 411 ~R 414 is synonymous with Y 1 ~Y 3 , Ar 1 , Ar 2 , m and n are each the Y 1 ~Y 3 , Ar 1 , Ar 2 , m and n are synonymous therewith; *1 and *2 are 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), 511 ~R 514 and R 520 is equivalent to

[0169] In the general formulae (110) to (117), R 511 ~R 514 and R 520 Among the groups of two or more adjacent groups, it is preferable that none of the groups of two or more adjacent groups are bonded to each other.

[0170] In the compound of this embodiment, Rx, R 1 , R 2 , R 3 , R 1A , R 2A , R 3A , R 21A , R 22A , R 11 ~R 18 and R 21 ~R 28 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. In the compound of this embodiment, R 311 ~R 318 , R 411 ~R 414 , R 415 , R 511 ~R 514 , R 520 , R 611 ~R 614 , R 620 , R 311B ~R 314B , R 411B ~R 414B 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.

[0171] In one embodiment, the compound represented by the general formula (1) contains at least one deuterium atom. In one embodiment, the compound represented by the general formula (1) does not contain a deuterium atom.

[0172] In the compound 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.

[0173] In the compound of this embodiment, the substituent in the case of being "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 this embodiment, the substituent in the case of being "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 this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0174] The compound of this embodiment is preferably a material used in the light-emitting layer. The compound of this embodiment is preferably a host material. The compound of this embodiment is preferably a sensitizing material. The compound of this embodiment is preferably a thermally activated delayed fluorescent compound. The compound of the present embodiment is preferably a sensitizing material and a thermally activated delayed fluorescent compound.

[0175] (Thermal activation delayed fluorescence) In this specification, thermally activated delayed fluorescence may be referred to as delayed fluorescence. Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is 13 It is explained that if the transition probability can be reduced, the reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, Figure 10.38 in the literature 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 level and the triplet level is used. Compounds that exhibit thermally activated delayed fluorescence (TADF properties) (hereinafter also referred to as TADF compounds) are known to have donor and acceptor sites bonded to each other in the molecule.

[0176] In general, delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0177] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a method of exciting a sample with a pulsed laser and measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission from TADF compounds is classified into emission components from singlet excitons generated during the first PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from the singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long life span. Thus, there is a large time difference between the emission from singlet excitons generated by the initial PL excitation and the emission from singlet excitons generated via triplet excitons. Therefore, it is possible to obtain the emission intensity derived from delayed fluorescence.

[0178] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Fig. 2. An example of a method for measuring transient PL and an analysis of the behavior of delayed fluorescence using Fig. 2 will be described.

[0179] 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.

[0180] The sample accommodated in the sample chamber 102 is obtained by forming a thin film, in which a doping material is doped at a concentration of 12 mass % relative to a matrix material, on a quartz substrate.

[0181] A pulsed laser is irradiated from a pulsed laser unit 101 to a thin film sample accommodated in a sample chamber 102 to excite the doping material. Emission light is extracted in a direction at 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by a spectrometer 103 to form 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. By cutting out this two-dimensional image at a predetermined time axis, an emission spectrum can be obtained in which the vertical axis is emission intensity and the horizontal axis is wavelength. Furthermore, by cutting out the two-dimensional image at the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis is the logarithm of emission intensity and the horizontal axis is time.

[0182] For example, the following compound HX1 was used as the matrix material, and the following compound DX1 was used as the doping material to prepare thin film sample A as described above, and transient PL measurement was performed.

[0183] [ka]

[0184] 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.

[0185] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0186] [ka]

[0187] As described above, the transient PL measurement can provide an emission decay curve with the emission intensity on the vertical axis and the time on the horizontal axis. 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 that decays slowly to the intensity of the fluorescence that decays quickly is somewhat large.

[0188] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength that the delayed fluorescent material absorbs. Delay luminescence This is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0189] The amount and ratio of prompt luminescence and delayed luminescence 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 amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2.

[0190] In addition, a sample prepared by the following method is used to measure the delayed fluorescence of the delayed fluorescent compound according to this embodiment. For example, the delayed fluorescent compound according to this embodiment is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption. In addition, in order to prevent quenching due to oxygen, the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above 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. The total fluorescence quantum yield is calculated using the fluorescence area intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0191] In this embodiment, the amount of prompt luminescence (instantaneous luminescence) of the compound to be measured is X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. The amounts and ratio of prompt luminescence and delayed luminescence of compounds other than the delayed fluorescent compound in this specification are measured in the same manner as the amounts and ratio of prompt luminescence and delayed luminescence of the delayed fluorescent compound according to this embodiment.

[0192] (ΔST) In this embodiment, the lowest excited singlet energy S1 and the energy gap T at 77 [K]77K Difference between (S1-T 77K ) is defined as ΔST.

[0193] The lowest excited singlet energy S1 (M2) of the compound of this embodiment (preferably a delayed fluorescent compound) and the energy gap T at 77 [K] of the compound of this embodiment 77K The difference ΔST(M2) from (M2) is preferably less than 0.5 eV, more preferably less than 0.3 eV, even more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the following formula (Math. 10), (Math. 1), (Math. 1A), (Math. 1B), or (Math. 1C). ΔST(M2)=S1(M2)-T 77K (M2)<0.5eV…(Number 10) ΔST(M2)=S1(M2)-T 77K (M2)<0.3eV…(Math 1) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV…(Several 1A) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV…(Math 1B) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV …(Math 1C)

[0194] (Relationship between triplet energy and energy gap at 77[K]) Here, a relationship between the triplet energy and the energy gap at 77 [K] will be described. In this embodiment, the energy gap at 77 [K] is different from the triplet energy that is usually defined. The triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77[K]). ) is measured, a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from a predetermined conversion formula based on the wavelength value at the intersection of the tangent line and the horizontal axis. Here, among the compounds according to this embodiment, the thermally activated delayed fluorescent compound is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), and the excited singlet state and the excited triplet state are mixed. 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 distinguish which state the light emission is from, but it is basically considered that the triplet energy value is dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish the difference 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 prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent and the horizontal axis is determined. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K Let us assume that. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0195] 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 of 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 the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using a spectrofluorometer body, model F-4500, manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[0196] (Lowest excited singlet energy S1) The method for measuring the lowest excited singlet energy S1 using a solution (sometimes referred to as a solution method) includes the following method. Prepare a 10 μmol / L toluene solution of the compound to be measured and place it in a quartz cell, then measure the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample at room temperature (300 K). Draw a tangent to the falling edge on the long wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0197] The tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction towards 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 at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the falling edge on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0198] (Method for producing the compound of this embodiment) The compound of this embodiment (the compound represented by the general formula (1)) can be produced according to the synthesis method described in the Examples described later, or by following the synthesis method and using known alternative reactions and raw materials suited to the target product.

[0199] (Specific examples of the compound of this embodiment) Specific examples of the compound of this embodiment include the following compounds, however, the present invention is not limited to these specific examples.

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[0228] Second Embodiment <Materials for organic electroluminescence devices> The material for organic electroluminescence devices according to this embodiment contains the compound according to the first embodiment (the compound represented by the general formula (1)). One aspect of the material for organic electroluminescence devices includes a material for organic electroluminescence devices that includes only the compound according to the first embodiment, and another aspect of the material for organic electroluminescence devices includes a material for organic electroluminescence devices that includes the compound according to the first embodiment and another compound different from the compound in the first embodiment. In the material for an organic electroluminescence device of this embodiment, the compound according to the first embodiment is preferably a host material. In this specification, when the compound according to the first embodiment is a host material, the host material is referred to as a first host material. The material for an organic electroluminescence device according to one embodiment may include a first host material (a compound according to the first embodiment) and another compound such as a dopant material. The material for an organic electroluminescence device according to one embodiment may include a first host material (a compound according to the first embodiment), a second host material different from the first host material, and a dopant material. In the material for organic electroluminescence devices according to one embodiment, the first host material is preferably a sensitizing material. In the material for organic electroluminescence devices according to one embodiment, the first host material is more preferably a sensitizing material and a delayed fluorescent compound.

[0229] Third Embodiment <Organic electroluminescence element> An organic EL element according to a third embodiment will be described. The organic EL device according to the third embodiment includes an organic layer between an anode and a cathode. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer includes a plurality of layers made of an organic compound stacked together. The organic layer may further include an inorganic compound. At least one layer of the organic layer includes the compound according to the first embodiment (the compound represented by general formula (1)) as compound M2.

[0230] (organic layer) In the organic EL device of the present embodiment, the organic layer may be, for example, composed of one light-emitting layer, or may include a layer that can be used in an organic EL device. The layer that can be used in an organic EL device is not particularly limited, and may be, for example, 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 organic layer has at least one emitting layer, and the emitting layer contains the compound M2. In one aspect of the organic EL device of this embodiment, the light-emitting layer contains the compound M2 as a first host material. In this case, the first host material is preferably a delayed fluorescent compound. 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.

[0231] In the organic EL device of this embodiment, a hole transport layer may be disposed between the anode and the light emitting layer.

[0232] In the organic EL device of this embodiment, an electron transport layer may be disposed between the cathode and the light emitting layer.

[0233] FIG. 1 shows a schematic configuration of one example of the 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 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 in this order from the anode 3 side. The present invention is not limited to the configuration of the organic EL element shown in FIG.

[0234] (Light 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 light-emitting layer, the first host material and the fluorescent material are contained in the single light-emitting layer, and when the organic EL device has multiple light-emitting layers, the first host material and the fluorescent material are contained in any one of the multiple light-emitting layers.

[0235] [First host material (compound M2)] In one embodiment, the first host material (compound M2) is a sensitizing material. In one embodiment, the light-emitting layer contains compound M2 as a sensitizing material. In one embodiment, the sensitizing material is a delayed fluorescent compound. In one embodiment, the light-emitting layer contains a sensitizing material as compound M2 and a fluorescent light-emitting material. 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.

[0236] [Fluorescent materials] 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 preferred that the fluorescent material is not a metal complex. In this specification, the compound used as the fluorescent material may be referred to as compound M3.

[0237] 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.

[0238] In this embodiment, the fluorescent material (compound M3) is preferably a compound represented by the following general formula (41).

[0239] [ka]

[0240] (In the general formula (41), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heterocycle having 5 to 50 ring atoms, 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, R 40 ~R 44 are each independently by combining with the ring a, ring b or ring c to form a substituted or unsubstituted monocycle, or combines with the ring a, ring b, or ring c to form a substituted or unsubstituted fused ring; not bonded to the ring a, ring b, or ring c; R 41 and R 42 teeth, joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 43 and R 44 teeth, joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 40 ~R 44 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, -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, R 45 teeth, 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 40are identical or different from each other, R 41 If there are multiple R 41 are identical or different from each other, R 42 If there are multiple R 42 are identical or different from each other, R 43 If there are multiple R 43 are identical or different from each other, R 44 If there are multiple R 44 are identical or different from each other, R 45 If there are multiple R 45 are either identical or different.)

[0241] In this embodiment, the compound represented by the general formula (41) is preferably a compound represented by the following general formula (410).

[0242] [ka]

[0243] (In the general formula (410), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or A substituted or unsubstituted heterocycle having 5 to 50 ring atoms, R 401 and R 402 are each independently by combining with the ring a, ring b or ring c to form a substituted or unsubstituted monocycle, or combines with the ring a, ring b, or ring c to form a substituted or unsubstituted fused ring; not bonded to the ring a, ring b, or ring c; R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 401 and R402 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, -CR 45 an iminyl group represented by =N; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0244] 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 formulae (41-1) to (41-6).

[0245] [ka]

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[0247] [ka]

[0248] (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 With R 421 ~R 423 A set of two or more adjacent 423 and R 402 With R 402 and R 424 With R424 ~R 427 A set of two or more adjacent 427 and R 412 and R 412 and R 411 and one or more pairs selected from the group consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 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, -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, R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 411 , R 412 , and R 421 ~R 427 each independently represents a hydrogen atom or a substituent R X and The substituent R X are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 ~R 907 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 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, R 902 If there are multiple R 902 are the same or different, R 903 If there are multiple R 903 are the same or different, R 904 If there are multiple R 904 , which may be the same or different, R 905 If there are multiple R 905 are the same or different, R 906 If there are multiple R 906 are the same or different, R 907 If there are multiple R 907 are either identical or different.) (In the general formula (41-2), Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 and R 401 and R 421 With R 421 ~R 423 A set of two or more adjacent 423 and R 402 With R 402 and R 424 With R 424 ~R 427 A set of two or more adjacent 413 and R 414 and R 414 and R 401 and one or more pairs selected from the group consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 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, -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, R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 413 , R 414 , and R421 ~R 427 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is equivalent to (In the general formula (41-3), Xa and Xb each independently represent O, S, Se, C(R 403 )(R 404 ), or NR 405 and R 401 and R 421 With R 421 ~R 423 A set of two or more adjacent 423 and R 402 With R 415 and R 416 With R 416 and R 412 and R 412 and R 411 and one or more pairs selected from the group consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 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, -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, R 403 ~R405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 411 , R 412 , R 415 , R 416 , and R 421 ~R 423 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is synonymous with R 403 If there are multiple R 403 are identical or different from each other, R 404 If there are multiple R 404 are identical or different from each other, R 405 If there are multiple R 405 are either identical 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 With R 421 ~R 423 A set of two or more adjacent R 423 and R 402 With R 402 and R 418 With R 418 and R 417 and R 412 and R 411 and one or more pairs selected from the group consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring.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, -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, R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 411 , R 412 , R 417 , R 418 , and R 421 ~R 423 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is synonymous with R 403 If there are multiple R 403 are identical or different from each other, R 404 If there are multiple R 404 are identical or different from each other, R 405 If there are multiple R 405 are either identical 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 With R 421 ~R423 A set of two or more adjacent 423 and R 402 With R 402 and R 418 With R 418 and R 417 With R 413 and R 414 and R 414 and R 401 and one or more pairs selected from the group consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 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, -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, R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 413 , R 414 , R 417 , R 418 , and R 421 ~R 423 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is synonymous with R 403If there are multiple R 403 are identical or different from each other, R 404 If there are multiple R 404 are identical or different from each other, R 405 If there are multiple R 405 are either identical or different.) (In the general formula (41-6), R 401 and R 421 With R 421 ~R 423 A set of two or more adjacent 423 and R 402 With R 402 and R 424 With R 424 ~R 427 A set of two or more adjacent 427 and R 428 With R 428 ~R 431 A pair of two or more adjacent 431 and R 401 and one or more pairs selected from the group consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 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, -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, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 421 ~R 431 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is equivalent to

[0249] In the compounds represented by the general formulas (41-1) to (41-5), R 412 and R 411 With R 413 and R 414 With R 415 and R 416 and R 417 and R 418 and 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.

[0250] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (41-7).

[0251] [ka]

[0252] (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 With R 421 ~R 423 A set of two or more adjacent 423 and R 402 With R 402 and R 424 With R424 ~R 427 A pair of two or more adjacent 437 ~R 440 At least one pair selected from the group consisting of adjacent pairs of two or more of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 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, R 403 ~R 405 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 421 ~R 427 and R 437 ~R 440 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is equivalent to

[0253] In this embodiment, R 401 and R 402are 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 further preferably a group represented by the following general formula (42).

[0254] [ka]

[0255] (In the general formula (42), R 432 ~R 436 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 432 ~R 436 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is synonymous with Multiple R 432 If multiple R 432 are the same or different, Multiple R 433 If multiple R 433 are the same or different, Multiple R 434 If multiple R 434 are the same or different, Multiple R 435 If multiple R 435 are the same or different, Multiple R 436 If multiple R 436 are the same or different, * indicates the bond position.)

[0256] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-1).

[0257] [ka] (In the general formula (42-1), R 421 ~R 431 are R in the general formula (41-6), 421 ~R 431 is synonymous with R 451 ~R 455 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 456 ~R 460 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 451 ~R 455 and R 456 ~R 460 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is equivalent to

[0258] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-2).

[0259] [ka]

[0260] (In the general formula (42-2), R 422 , R 426 , R 429 , R 453 , and R 458 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is equivalent to

[0261] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-3).

[0262] [ka]

[0263] (In the general formula (42-3), R 421 ~R 427 , R 437 ~R 440 and Xa are each R in the general formula (41-7). 421 ~R 427 , R 437 ~R 440 and Xa, R 451 ~R 455 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 456 ~R 460 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 451 ~R 455 and R 456 ~R 460 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is equivalent to

[0264] In this embodiment, the compound represented by the general formula (41) is also preferably a compound represented by the following general formula (42-4).

[0265] [ka]

[0266] (In the general formula (42-4), Xa has the same meaning as Xa in the general formula (41-6), and R 422 , R 426 , R 429 , R 439 , R 453 , and R 458 each independently represents a hydrogen atom or a substituent R X and the substituent R X is the substituent R in the general formula (41-1). X is equivalent to

[0267] In this embodiment, R in compound M 422 , R 426 , 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 further preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0268] In this embodiment, it is preferable that Xa and Xb in compound M3 are each independently O or S.

[0269] (Method for producing the compound represented by formula (41)) The compound represented by the general formula (41) can be produced by a known method. The compound represented by the general formula (41) can also be produced by following a known method and using known alternative reactions and raw materials suited to the target product.

[0270] (Specific examples of compounds represented by formula (41)) Specific examples of the compound represented by the general formula (41) include the compounds shown below. In the specific examples, Me represents a methyl group, tBu represents a tertiary butyl group, and Ph represents a phenyl group.

[0271] [ka]

[0272] [ka]

[0273] [ka]

[0274] [ka]

[0275] 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, R 901a ~R 907a each independently represents a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901a If there are two or more, there are two or more R 901a are the same or different, and R 902a If there are two or more, there are two or more R 902a are the same or different, and R 903a If there are two or more, there are two or more R 903a are the same or different, and R 904a If there are two or more, there are two or more R 904a are the same or different, and R 905a If there are two or more, there are two or more R 905a are the same or different, and R 906a If there are two or more, there are two or more R 906a are the same or different, and R 907a If there are two or more, there are two or more R 907a are the same as or different from each other.

[0276] 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.

[0277] 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.

[0278] (Maximum peak wavelength) In this embodiment, the maximum peak wavelength of the compound M3 as the fluorescent material is preferably 480 nm or less, and more preferably 475 nm or less. In this embodiment, the maximum peak wavelength of the compound M3 as the fluorescent material is preferably 430 nm or more, and more preferably 440 nm or more. In this specification, the maximum peak wavelength of fluorescent light is defined as the maximum peak wavelength λ FL It is sometimes referred to as. In the organic EL device of the present 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 within the range of 430 nm or more and 480 nm or less.

[0279] (Emission spectrum half width) In this embodiment, the emission spectrum half width FWHM of the compound M3 as the fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less. In this embodiment, the emission spectrum half width FWHM of the compound M3 as the fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. FWHM is an abbreviation for full width at half maximum.

[0280] In this specification, the maximum fluorescence emission peak wavelength λ FL The compound to be measured is 10 -6 Moles / liter or more, 10 -5The maximum peak wavelength λ of the fluorescence spectrum at which the emission intensity is maximum in the measured fluorescence spectrum for a toluene solution dissolved at a concentration of 1 mole / liter or less 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.

[0281] (Stokes shift) In this embodiment, the Stokes shift of the compound M3 as the fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less. In this embodiment, the Stokes shift of the compound M3 as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. Compound M3 has a Stokes shift of 20 nm or less, so that the excitation energy can be reduced. Compound M3 has a Stokes shift of 10 nm or more, which makes it possible to suppress self-absorption and reduce efficiency loss. The Stokes shift can be measured by the following method. -5 The compound to be measured is dissolved in toluene at a concentration of 1.0 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 (300K) to measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength). A spectrophotometer can be used to measure the absorption spectrum, for example, a Hitachi High-Tech Science U-3900 / 3900H spectrophotometer. The compound to be measured is dissolved in 4.9 x 10 -6The measurement sample is prepared by dissolving the sample in toluene at a concentration of mol / L. The measurement sample is placed in a quartz cell and irradiated with excitation light at room temperature (300K) to measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength). A spectrophotometer can be used to measure the fluorescence spectrum, for example, Hitachi High-Tech Science's F-7000 spectrofluorophotometer. From these absorption and fluorescence spectra, the difference between the maximum absorption wavelength and the maximum fluorescence wavelength is calculated to determine the Stokes shift (SS). The unit of Stokes shift SS is nm.

[0282] (Relationship between sensitizing material and fluorescent material in the light-emitting layer) In one embodiment, the sensitizing 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 sensitizing material, the emitting layer does not contain a phosphorescent metal complex.

[0283] FIG. 4 is a diagram showing an example of the relationship between the energy levels of a sensitizing material and a fluorescent material when the light-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 the Förster type 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) by 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.

[0284] In one embodiment, when the compound M2 is a sensitizing material, it is preferable that the minimum excited singlet energy S1(GT2) of the sensitizing material and the minimum excited singlet energy S1(D) of the fluorescent material satisfy the relationship of the following mathematical formula (Mathematical Formula 4). S1(GT2)>S1(D) ... (Number 3)

[0285] In one embodiment, when the compound M2 is a sensitizer, the energy gap T 77K (GT2) and the energy gap T of the fluorescent material at 77[K] 77K It is also preferable that (A) and (D) satisfy the relationship of the following mathematical formula (Mathematical Formula 6A). T 77K (GT2)>T 77K (D) ...(Math 6A)

[0286] When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in the light-emitting layer.

[0287] The maximum peak wavelength of the light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0288] (Compound content in light-emitting layer) The contents of the first host material (compound M2) and the fluorescent material (compound M3) contained in the light-emitting layer are preferably within the following ranges, for example. The content of compound M2 is preferably from 10% by mass to 80% by mass, more preferably from 10% by mass to 60% by mass, and further preferably from 20% by mass to 60% by mass. The content of compound M2 may be from 90% by mass to 99.9% by mass, from 95% by mass to 99.9% by mass, or from 99% by mass to 99.9% by mass. The content of compound M3 is preferably from 0.01% by mass to 10% by mass, more preferably from 0.01% by mass to 5% by mass, and further preferably from 0.01% by mass to 1% by mass. In this embodiment, the light-emitting layer may contain materials other than the compound M2 and the compound M3. The light-emitting layer may contain only one type of compound M2 or may contain two or more types of compound M3.

[0289] The structure of the organic EL element will be further described.

[0290] (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. An inorganic deposition film can also be used.

[0291] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, and the like. 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), and the like.

[0292] These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which zinc oxide is added to indium oxide at 1 mass % or more and 10 mass % or less. In addition, indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method by using a target in which tungsten oxide is added to indium oxide at 0.5 mass % or more and 5 mass % or less and zinc oxide is added to indium oxide at 0.1 mass % or more and 1 mass % or less. In addition, it may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method, or the like.

[0293] 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 easily injects holes regardless of the work function of the anode, so that materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as other elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0294] Materials with small work functions, such as elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these, can also be used. When alkali metals, alkaline earth metals, and alloys containing these are used to form the anode, vacuum deposition and sputtering methods can be used. Furthermore, when silver paste or the like is used, coating and inkjet methods can be used.

[0295] 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 optical transparency or semi-transparency metal material can be appropriately selected from the materials listed in the above section on the anode.

[0296] When the organic EL element 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 light reflectivity. In this specification, light reflectivity means a property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light emitting layer. The metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode. The anode may be composed of only a reflective layer, but may also have a multi-layer 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 is disposed between the reflective layer and the hole transport zone. The conductive layer can be appropriately selected from the materials listed in the above section on the anode.

[0297] (cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

[0298] 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.

[0299] By providing an electron injection layer, the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0300] When the organic EL element is a bottom emission type, the cathode is a reflective electrode. The reflective electrode is preferably made of a metal material having light reflectivity. The metal material having light reflectivity can be appropriately selected from the materials listed in the cathode section.

[0301] When the organic EL element is a top-emission type, the cathode is preferably formed of a metal material having optical transparency or semi-transparency that transmits light from the light-emitting layer. The optical transparency or semi-transparency metal material can be appropriately selected from the materials listed in the cathode section.

[0302] The organic EL element according to this embodiment may be a bottom-emission type organic EL element, or a top-emission type organic EL element. When the organic EL element is of 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 reflection. When the organic EL element is of a top emission type, it is preferable that the anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmittance.

[0303] (capping layer) When the organic EL device is of a top-emitting type, the organic EL device usually includes a capping layer on top of 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 contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives. Furthermore, a laminate in which layers containing these substances are laminated can also be used as the capping layer.

[0304] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. In addition, examples of materials 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, Other examples of aromatic amine compounds 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). In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can be used. For example, polymer compounds such as 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), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used. In addition, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be used.

[0305] (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 A material having a hole mobility of 0.1 V or more. The hole transport layer may be made of carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used. However, other substances may be used as long as they have a higher hole transporting property than an electron transporting property. Note that the layer containing the substance having a high hole transporting property may be a single layer or a layer in which two or more layers made of the above-mentioned substances are stacked.

[0306] (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, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used as low molecular weight organic compounds. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(pt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances mentioned here are mainly 10 -6 cm 2The electron transport layer is a material having an electron mobility of 1 / Vs or more. Note that, as long as the material has a higher electron transporting property than a hole transporting property, any material other than the above may be used as the electron transport layer. The electron transport layer may be a single layer or a layer in which two or more layers made of the above materials are stacked. The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0307] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), or compounds thereof can be used. In addition, a substance having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide. Furthermore, a Lewis base such as magnesium oxide can also be used. Furthermore, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0308] (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, e.g., a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method, e.g., a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0309] (Film thickness) The thickness of each organic layer of the organic EL element according to the present embodiment is not limited unless otherwise specified above. In general, if the thickness is too thin, defects such as pinholes are likely to occur, and if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the thickness of each organic layer of the organic EL element is usually preferably in the range of several nm to 1 μm.

[0310] Fourth Embodiment The configuration of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be given the same reference numerals or names, and the description will be omitted or simplified. In the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0311] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer further contains a second host material, but is otherwise similar to the organic EL device according to the third embodiment. In this specification, the compound used as the second host material may be referred to as compound M1. In one embodiment, the light-emitting layer contains a second host material (compound M1), a first host material (compound M2), and a fluorescent light-emitting material (compound M3).

[0312] (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 device has one light-emitting layer, the second host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer, and when the organic EL device 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.

[0313] 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.

[0314] [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 (101) to (118).

[0315] [ka]

[0316] [ka]

[0317] (In the general formula (101), A 11 ~A 16 are each independently a nitrogen atom, CR 11 or a carbon atom bonded to another atom or other structure in the molecule of compound M1, However, A 11 ~A 16 At least one of the carbon atoms is bonded to another atom or another structure in the molecule of the compound M1, R 11 If there are multiple R 11 are the same or different, and multiple R 11 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (102), A1 to A4 each independently represent a nitrogen atom, CR 12 or a carbon atom bonded to another atom or other structure in the molecule of compound M1, R 12 are each independently a hydrogen atom or a substituent, or an adjacent R 12 one or more of the pairs of the rings are bonded to each other to form a ring, R 12 If there are multiple R 12 are the same or different, and multiple R 12 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, X 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 18 and a carbon atom bonded to another atom or other structure in the molecule of the compound M1, or R 19 and a silicon atom bonded to another atom or other structure in the molecule of the compound M1, However, the carbon atoms in A1 to A4, X 10 Nitrogen atom in X 10 Carbon atoms and X in 10 At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the compound M1, R 14 and R 15 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 16 and R 17 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (103), R 115 and R 116 A set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formulae (101) to (104), R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 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 117 are each independently 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(R917 )(R 918 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the general formulae (103) to (118), * represents a bonding site to another atom or another structure in the molecule of the compound M1, When the compound M1 has a plurality of partial structures represented by each of the general formulae (101) to (104), The partial structures represented by the general formula (101) are the same or different from each other, A plurality of partial structures represented by the general formula (102) are the same or different from each other, A plurality of partial structures represented by the general formula (103) are the same or different from each other, The partial structures represented by the general formula (104) are the same or different from each other.

[0318] (In the compound M1, R 901 ~R 918 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or 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, R903 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 914 If there are multiple R 914 are the same or different from each other, R 915 If there are multiple R 915 are the same or different from each other, R 916 If there are multiple R 916 are the same or different from each other, R917 If there are multiple R 917 are the same or different from each other, R 918 If there are multiple R 918 are either identical or different.)

[0319] In the general formula (102), X 10 is "a nitrogen atom bonded to another atom or another structure in the molecule of compound M1", the general formula (102) is represented by the following general formula (102-1). In the general formula (102), X 10 "R 18 and a carbon atom bonded to another atom or another structure in the molecule of compound M1”, the general formula (102) is represented by the following general formula (102-2). In the general formula (102), X 10 "R 19 and a silicon atom bonded to another atom or another structure in the molecule of compound M1”, the general formula (102) is represented by the following general formula (102-3). In the general formulae (102-1) to (102-3), A1 to A4 are each independently defined as A1 to A4 in the general formula (102), 18 and R 19 each independently represents R in the general formula (102) 12 and * denotes a bonding site to another atom or other structure in the molecule of compound M1.

[0320] [ka]

[0321] In one embodiment, the second host material has at least one partial structure represented by the general formula (101). In one embodiment, the partial structure represented by the general formula (101) is at least one selected from the group consisting of partial structures represented by the following general formulae (A11) to (A19).

[0322] [ka]

[0323] [ka]

[0324] (In the general formulae (A11) to (A16), A 12 ~A 16 each independently represents a nitrogen atom or CR 11 and R 11 is R in the general formula (101). 11 and * represents a bonding site to another atom or another structure in the molecule of the compound M1. In the general formulae (A17) and (A18), A 11 ~A 22 each independently represents a nitrogen atom or CR 11 or a carbon atom bonded to another atom or structure in the molecule of compound M1, R 11 each independently represents R in the general formula (101). 11 is synonymous with A 11 ~A 22 At least one of the carbon atoms is bonded to another atom or another structure in the molecule of the compound M1, In the general formula (A19), A 11 ~A 18 each independently represents a nitrogen atom or CR 11 or a carbon atom bonded to another atom or structure in the molecule of compound M1, R 11 each independently represents R in the general formula (101). 11 is synonymous with X 11 and X 12 each independently represents X in the general formula (102). 10 and A 11 ~A 18 Carbon atom in X 11and X 12 Nitrogen atom in X 11 and X 12 Carbon atoms in and X 11 and X 12 At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the compound M1, In the general formulae (A11) to (A19), * represents a bonding site to another atom or another structure in the molecule of the compound M1.

[0325] In one embodiment, the second host material has at least one partial structure represented by the general formula (102). In one embodiment, the partial structure represented by the general formula (102) is at least one selected from the group consisting of partial structures represented by the following general formulae (B11) to (B24).

[0326] [ka]

[0327] In the general formulae (B11) to (B16), Ax1 to Ax4 each independently represent a nitrogen atom or CR 12 and R 12 each independently represents R in the general formula (102) 12 is synonymous with X 10 is X in the general formula (102). 10 and * represents a bonding site to another atom or another structure in the molecule of the compound M1. In the general formula (B17), Ax1, Ax2 and Ay1 to Ay4 each independently represent a nitrogen atom or CR 12 or a carbon atom bonded to another atom or structure in the molecule of compound M1, R 12 each independently represents R in the general formula (102) 12 is synonymous with X 10 is X in the general formula (102). 10wherein Ax1, Ax2, and Ay1 to Ay4 are carbon atoms, and X 10 Nitrogen atom in X 10 Carbon atoms and X in 10 At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the compound M1, In the general formula (B18), Ay1 to Ay8 each independently represent a nitrogen atom or CR 12 or a carbon atom bonded to another atom or structure in the molecule of compound M1, R 12 each independently represents R in the general formula (102) 12 is synonymous with X 10 is X in the general formula (102). 10 The carbon atoms in Ay1 to Ay8, X 10 Nitrogen atom in X 10 Carbon atoms and X in 10 At least one of the silicon atoms in is bonded to another atom or another structure in the molecule of the compound M1, In the general formulae (B11) to (B18), * represents a bonding site to another atom or another structure in the molecule of the compound M1.

[0328] [ka]

[0329] (In the general formulae (B19) to (B24), Ay1 to Ay8 and Ay9 to Ay 12 each independently represents a nitrogen atom or CR 12 or a carbon atom bonded to another atom or structure in the molecule of compound M1, R 12 each independently represents R in the general formula (102) 12 X9 and X 10 each independently represents X in the general formula (102). 10 is synonymous with Ay1-Ay8 and Ay9-Ay 12Carbon atoms in X9 and X 10 Nitrogen atoms, X9 and X 10 Carbon atoms in, and X9 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.

[0330] In the compound M1 of this embodiment, R 11、 R 12 and R 115 ~R 117 are preferably 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. In the compound M1 of this embodiment, R 11、 R 12 and R 115 ~R 117are each independently preferably 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. In the compound M1 of this embodiment, R 11、 R 12 and R 115 ~R 117 is more preferably a hydrogen atom.

[0331] In the first compound of this embodiment, X 10 R in 13 ~R 19 , and R in X9 13 ~R 19 (X 10 R in 13 ~R 19 (same meaning as above) are preferably each independently a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms. In the compound M1 of this embodiment, X 10 R in 13 ~R 19 , and R in X9 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. In the compound M1 of this embodiment, X10 R in 13 ~R 19 , and R in X9 13 ~R 19 It is more preferable that each of the is independently an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0332] Examples of the partial structure represented by any one of the general formulae (101) to (118) include partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125). It is also preferable that compound M1 contains at least one of partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125) in one molecule.

[0333] [ka]

[0334] In the general formulae (A101) to (A107), R 101 ~R 106 each independently represents R in the general formula (101). 11 is synonymous with R 101 ~R 106 At least one of these is a single bond that bonds to another atom or other structure in the molecule of the compound M1. In the general formulae (A101) to (A107), adjacent 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 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.

[0335] [ka]

[0336] In the general formulae (A108) to (A109), R 110 each independently represents R in the general formula (101). 11 is synonymous with R 110 At least one of R 110 are the same or different, and multiple R 110 one or more of a set of two or more adjacent groups among

[0337] [ka]

[0338] In the general formulae (A110) to (A114), R 110 and R 112 ~R 114 each independently represents R in the general formula (101). 11 is synonymous with X 110 each independently represents X in the general formula (102). 10 where R 110 and R 112 ~R 114 At least one of X is a single bond 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 are the same or different from each other. In the general formulae (A110) to (A114), a plurality of R 110 A set of two or more adjacent 112and R 113 Set of X 110 R in 14 and R 15 The set of (X 10 R in 15 and R 15 (same as the set of X 110 R in 16 and R 17 The set of (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, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0339] [ka]

[0340] In the general formulae (A115) to (A119), R 110 and R 112 ~R 114 each independently represents R in the general formula (101). 11 where R 110 and R 112 ~R 114 At least one of R 110 are the same or different from each other. In the general formulae (A115) to (A119), a plurality of R 110 A pair of two or more adjacent 112 and R 113 one or more of the pairs are 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.

[0341] [ka]

[0342] In the general formulae (A120) to (A121), R 110 each independently represents R in the general formula (101). 11 where R 110 At least one of R 110 are the same or different from each other. In the general formulae (A120) to (A121), a plurality of R 110 one or more of a set of two or more adjacent groups among

[0343] [ka]

[0344] In the general formulae (B101) to (B109), R 114 and R 121 ~R 131 each independently represents R in the general formula (102) 12 where R 114 and R 121 ~R 131 At least one of these is a single bond that bonds to another atom or other structure in the molecule of the compound M1. In the general formulae (B101) to (B102), R 122 and R 123 Group R 123 and R 114 and R 114 and R 121 one or more of the pairs 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. In the general formulae (B105) and (B106), R 124 and R 125 Group R 125 and R 126 Group R 126 and R127 Group R 127 and R 128 and R 128 and R 129 one or more of the pairs 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. In the general formula (B107), R 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 124 one or more of the pairs 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. In the general formulae (B108) to (B109), R 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 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.

[0345] [ka]

[0346] In the general formulae (B110) to (B117), R 110 and R 132 ~R 135 each independently represents R in the general formula (102) 12 where R 110 and R132 ~R 135 At least one of R 110 are the same or different from each other. In the general formulae (B110) to (B117), a plurality of R 110 A pair of two or more adjacent 132 and R 133 one or more of the pairs 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.

[0347] [ka]

[0348] In the general formulae (B118) to (B123), R 110 each independently represents R in the general formula (102) 12 Xa and Xb each independently represent X in the general formula (102). 10 where R 110 At least one of Xa and Xb is a single bond bonded to another atom or structure in the molecule of the compound M1, or at least one of the nitrogen atom, carbon atom, and silicon atom in Xa and Xb is bonded to another atom or structure in the molecule of the compound M1, and a plurality of R 110 are the same or different from each other. In the general formulae (B118) to (B123), a plurality of R 110 A pair of adjacent two or more of Xa, R 14 and R 15 and R in Xb 14 and R 15 The set of (X 10 R in 14 and R 15 (same meaning as the set of Xa and R in Xa) 16 and R 17 and R in Xb 16 and R17 The set of (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, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0349] [ka]

[0350] In the general formulae (B124) and (B125), R 110 each independently represents R in the general formula (102) 12 Xa, Xb and Xc each independently represent X in the general formula (102). 10 where R 110 At least one of Xa, Xb, and Xc is a single bond bonded to another atom or structure in the molecule of the compound M1, or at least one of the nitrogen atom, carbon atom, and silicon atom in Xa, Xb, and Xc is bonded to another atom or structure in the molecule of the compound M1, and a plurality of R 110 are the same or different from each other. In the general formulae (B124) to (B125), a plurality of R 110 R in Xa, Xb, and Xc 14 and R 15 The set of (X 10 R in 14 and R 15 (same meaning as the set of Xa, Xb and Xc) and R 16 and R 17 The set of (X 10 InokeR 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, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other.

[0351] In the above 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 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, 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; More preferably, it is an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0352] In the general formulae (A101) to (A121) and (B101) to (B125), Xa, Xb, Xc and X 110 R in 13 ~R 19 (X 10 R in 13 ~R 19 (same meaning as above) are each preferably 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, 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; More preferably, it is an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0353] In this embodiment, it is preferable that compound M1 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.

[0354] In this embodiment, it is more preferable that compound M1 (III) has at least one cyano group, or (IV) 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 fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.

[0355] 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.

[0356] In this embodiment, the compound M1 preferably has at least one monovalent or higher residue derived from a substituted or unsubstituted carbazole.

[0357] In this embodiment, the compound M1 preferably has at least one partial structure represented by the following general formula (15).

[0358] [ka]

[0359] (In the general formula (15), R 150 ~R 158 at least one of the above is a single bond that bonds to another atom or another structure in the molecule of the compound M1; R that is not a single bond 150 ~R 158 are each independently Hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by -C(=O)R 908 A group represented by -COOR 909 A group represented by -P(=O)(R 910 )(R 911 ) a group represented by -Ge(R 912 )(R 913 )(R 914 ) a group represented by -B(R 915 )(R 916 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0360] 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.

[0361] (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 the following general formula (162).

[0362] [ka]

[0363] (In the general formula (161), Ar 161 teeth, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or A substituted or unsubstituted heterocycle 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 It bonds to the elements that make up If m1 is 2 or more, multiple R 161 are the same or different, However, Ar 161 is not an electron-accepting aromatic hydrocarbon ring or heterocycle, but an Ar 161 When the group has a substituent, the substituent is not an electron accepting group, In the general formula (162), Ar 162 teeth, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or A substituted or unsubstituted heterocycle having 5 to 30 ring atoms, n1 is 1, 2, 3, 4, 5 or 6; R 162 is an electron accepting group, and R 162 are respectively Ar 162 It bonds to the elements that make up If n1 is 2 or more, multiple R 162 are the same or different, However, Ar 162 is not an electron donating aromatic hydrocarbon ring or heterocycle, but an Ar 162 When has a substituent, the substituent is not an electron-donating group.

[0364] In the general formulae (161) and (162), Ar 161 and Ar 162 are each preferably independently a monovalent or higher residue derived from any of the compounds represented by the following general formulae (A61), (A62) and (A63).

[0365] [ka]

[0366] (In the general formulae (A61) to (A63), X Dis an oxygen atom or a sulfur atom, R D is a hydrogen atom or a substituent.

[0367] In the general formula (A3), R D When is a substituent, examples of the substituent include R 11 The same groups as those shown below can be mentioned.

[0368] In this embodiment, R in the general formula (161) 161 are preferably each independently a monovalent or higher 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).

[0369] [ka]

[0370] (In the above general formula (DN7), * represents Ar 161 It represents the bonding site with the elements that make up the element.)

[0371] In this embodiment, R in the general formula (162) 162 are preferably each independently a monovalent or higher 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).

[0372] [ka]

[0373] [ka]

[0374] (In the general formula (AC1), n A is 1, 2 or 3, In the general formulae (AC22) to (AC23), X1 to X8 each independently represent CR 163 or a carbon atom bonded to another atom or another structure in the molecule of the compound M1, provided that at least one of the carbon atoms in X1 to X8 is Ar 162 It combines with the elements that make up In the general formula (AC24), X1 to X8 each independently represent a nitrogen atom or CR 163 or Ar 162 A carbon atom bonded to the elements that make up In the general formulae (AC22) to (AC24), R 163 If there are multiple R 163 are the same or different, and multiple R 163 At least one pair of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 163 each independently represents R in the general formula (102) 12 is synonymous with 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 element.)

[0375] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (13).

[0376] [ka]

[0377] (In the general formula (13), X 13 is an oxygen atom, a sulfur atom, or a group represented by N-Rb, Z1~Z 12 are each independently a nitrogen atom or a group represented by C-Rc, Ar 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 are each independently 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 Hydrogen atoms, 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 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 Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When a plurality of Rc's are present, the plurality of Rc's are the same or different.

[0378] In the compound represented by the general formula (13), -L 14 -Ar 14 and -L 15 -Ar 15 When Z1 and Z 12 , Z2 and Z 11 , Z3 and Z 10 It is also preferable that Z4 and Z9, Z5 and Z8, and Z6 and Z7 are not all the same groups. In this case, in the general formula (13), X 13 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, which is different from the structure fused to the left side of a 5-membered ring containing the following:

[0379] In the compound represented by the general formula (13), -L 14 -Ar 14 and -L 15 -Ar 15 In this case, too, the compound represented by the general formula (13) has an asymmetric structure, as described above.

[0380] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (12).

[0381] [ka]

[0382] (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 are each independently 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 teeth, 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; 13 are the same or different from each other, X1 to X8 and Y1 to Y8 each independently represent N or CRa; However, one of X5 to X8 and one of Y1 to Y4 are L 13 is a carbon atom bonded via or directly to Ra is independently Hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; -Si(R 901 )(R 902 )(R 903 ) a group represented by Halogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When a plurality of Ra are present, the plurality of Ra are the same or different, The compound represented by the general formula (12) satisfies one or both of the following (i) and (ii): (i) Ar 11 and Ar 12 At least one of the groups is an aryl group having 6 to 50 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 50 ring atoms substituted with a cyano group. (ii) At least one of X1 to X4 and Y5 to Y8 is CRa, and at least one of Ra in X1 to X4 and Y5 to Y8 is an aryl group having 6 to 50 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 50 ring atoms substituted with a cyano group.

[0383] 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.

[0384] 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, one of X5 to X8 and one of Y1 to Y4 are directly bonded via a single bond.

[0385] In the compound represented by the general formula (12), any pair selected from the group consisting of a pair of X6 and Y3, a pair of X6 and Y2, and a pair of X7 and Y3 is L 13 It is preferable that the carbon atom is bonded via a carbon atom bonded directly to the ring.

[0386] The pair of X6 and Y3 is L 13 When the carbon atom is bonded via or directly bonded, the compound represented by general formula (12) is represented by the following general formula (121).

[0387] [ka]

[0388] (In the above general formula (121), Ar 11 , Ar 12 , L 11 , L 12 , L 13 , m, X1 to X5, X7 to X8, Y1 to Y2, and Y4 to Y8 each represent the general formula (12). Ar in 11 , Ar 12 , L 11 , L 12 , L 13 , m, X1 to X5, X7 to X8, Y1 to Y2, and Y4 to Y8 are the same as those in the formula (121), and the compound represented by the formula (121) satisfies at least one of the conditions (i) and (ii).

[0389] In the compound represented by the general formula (12), -Ar 11 -L 11 and a group represented by -Ar 12 -L 12 It is preferable that the groups represented by the following formula (I) are different from each other.

[0390] L 13 The monocyclic hydrocarbon group having 6 or less ring carbon atoms as 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. L 13 The monocyclic heterocyclic group having 6 or less ring atoms as 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.

[0391] 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 the light-emitting efficiency is expected to be improved. Furthermore, by forming an exciplex with two or more compounds M1 (second host material), the excitation energy is reduced, and a lower voltage drive is possible than when one type of second host material is contained in the light-emitting layer.

[0392] (Production method of 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.

[0393] (Specific example 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.

[0394] [ka]

[0395] [ka]

[0396] [ka]

[0397] [ka]

[0398] [ka]

[0399] [ka]

[0400] [ka]

[0401] (Relationship between the second host material, the sensitizing material and the fluorescent material in the light-emitting layer) In one embodiment, the sensitizing material 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 sensitizing material, and the fluorescent material when the light-emitting layer contains a second host material (compound M1), a delayed fluorescent compound (compound M2) as a sensitizing 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 the Forster type 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 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) by 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.

[0402] In one embodiment, the energy gap T at 77[K] of the second host material 77K (H2) and the energy gap T of the sensitizer at 77[K] 77K It is preferable that (G2) satisfies the relationship of the following mathematical formula (Mathematical Formula 1). T 77K (H2)>T 77K (G2) …(Number 1)

[0403] In one embodiment, it is also preferable that the lowest excited singlet energy S1(H2) of the second host material and the lowest excited singlet energy S1(GT2) of the sensitizing material satisfy the relationship of the following mathematical formula (Mathematical Formula 4A). S1(H2)>S1(GT2) ...(Math 4A)

[0404] In one embodiment, it is also preferable that the lowest excited singlet energy S1 of the second host material, the sensitizing material, and the fluorescent material satisfy the relationship of the following mathematical formula (Mathematical Formula 4B). S1(H2)>S1(GT2)>S1(D)…(Number 4B)

[0405] 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 satisfies the relationship of the following formula (Mathematical formula 6B). T 77K (H2)>T 77K (GT2)>T 77K (D) …(Number 6B)

[0406] (Compound content in light-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 light-emitting layer are preferably within the following ranges, for example. The content of compound M1 in the light-emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more. The content of compound M1 in the light-emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.

[0407] The content of compound M2 is preferably 5% by mass or more, and more preferably 10% by mass or more. The content of compound M2 is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0408] 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 the compound M1, the compound M2, and the compound M3 in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the light-emitting layer containing materials other than the compound M1, the compound M2, and the compound M3. In this embodiment, the light-emitting layer may contain only one type of compound M1, or may contain two or more types. In this embodiment, the light-emitting layer may contain only one type of compound M2, or may contain two or more types. In this embodiment, the light-emitting layer may contain only one type of compound M3, or may contain 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.

[0409] (Thickness of the light-emitting layer) The thickness of the light-emitting layer in the organic EL element of this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the thickness is 5 nm or more, the formation of the light-emitting layer and the adjustment of the chromaticity tend to be easy, and when the thickness is 50 nm or less, an increase in the driving voltage is easily suppressed.

[0410] The organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0411] Fifth Embodiment (electronic equipment) The electronic device according to the fifth embodiment is equipped with the organic EL element according to any of the above-mentioned embodiments. The electronic device according to the fifth embodiment may be equipped with the organic EL element according to any of the sixth embodiment described later. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lamps. The light-emitting device can be used in a display device, and can be used, for example, as a backlight for a display device.

[0412] The display device as the electronic device according to the fifth embodiment is preferably an organic EL display device having organic EL elements as red, green and blue pixels, and the red pixel in this organic EL display device is preferably the organic EL element according to the third or fourth embodiment.

[0413] Sixth Embodiment The organic EL device according to the sixth 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 (a compound represented by the general formula (1)) as a first host material, and a phosphorescent metal complex as a dopant material. The 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 (a compound represented by the 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.

[0414] (Phosphorescent Metal Complexes) In one embodiment, the phosphorescent metal complex preferably comprises a heavy metal atom.

[0415] 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 (Au), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).

[0416] In one embodiment, the phosphorescent metal complex is preferably a compound represented by the following general formula (21). M(L1) n1 (L2) n2 …(twenty one)

[0417] [ka]

[0418] (In the above general formulae (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; L1 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; L2 is at least one ligand selected from the group consisting of monodentate ligands, bidentate ligands, and tridentate ligands; n2 is 0, 1, 2, 3 or 4; ring CY1, ring CY2, ring CY3 and ring CY4 are each 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; Y1 to Y4 each independently represent Single bond, 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, *aO-*b, *aS-*b, *aC(=O)-*b, *aS(=O)-*b, *aC(R5)(R6)-*b, *aC(R5)=C(R6)-*b, *aC(R5)=*b, *a-Si(R5)(R6)-*b, *aB(R5)-*b, *aN(R5)-*b, and *aP(R5)-*b; a1, a2, and a3 each independently represent 1, 2, or 3; a4 is 0, 1, 2 or 3, and when a4 is 0, the CY2 ring and the CY4 ring are not linked to each other; T1, T2, T3 and T4 are each independently chemical bond, *aO-*b, *aS-*b, *aB(R7)-*b, *aN(R7)-*b, *aP(R7)-*b, *aC(R7)(R8)-*b, *a-Si(R7)(R8)-*b, *a-Ge(R7)(R8)-*b, *aC(=O)-*b and *aC(=S)-*b; *a and *b each independently represent a bonding position to an adjacent atom, *1, *2, *3 and *4 are bonding positions with M. R1 to R8 each independently represent Hydrogen atoms, Halogen atoms, Cyano group, Nitro group, Amidino group, hydrazino group, 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 heteropolycyclic group; -Si(R 251 )(R 252 )(R 253 ) a group represented by -O-(R 254 ) a group represented by -S-(R 255 ) a group represented by -N(R 256 )(R 257 ) a group represented by -C(=O)R 258 A group represented by -C(=O)(OR 259 ) a group represented by -S(=O)2(OR 260 ) a group represented by -OP(=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 )(R269 ) 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 ) a group represented by -P(=S)(R 274 )(R 275 ) is selected from the groups represented by One or more pairs of adjacent two or more of R1 to R8 are joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, One or more pairs of adjacent two or more of R1 to R8 and Y1 to Y4 are joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, b1, b2, b3, and b4 each independently represent 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; R 251 ~R 275 are each independently Hydrogen atoms, Halogen atoms, -O-(R 276 ) a group represented by -N(R 277 )(R 278 ) a group represented by Cyano group, Nitro group, Amidino group, hydrazino group, 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; 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 heteropolycyclic group; selected from the group consisting of biphenylyl and terphenylyl groups; R 276 ~R 278 are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0419] In the present specification, a carbocyclic group having 5 to 30 ring carbon atoms means a monocyclic group or polycyclic group having 5 to 30 carbon atoms containing only carbon as a ring-forming atom. 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 connected to the carbocyclic group having 5 to 30 ring carbon atoms, various modifications are possible, such as the carbocyclic group having 5 to 30 ring carbon atoms being a trivalent group or a tetravalent group.

[0420] In this specification, a heterocyclic group having 1 to 30 ring carbon atoms means 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).

[0421] In this specification, a heterocycloalkyl group having 3 to 50 ring atoms means a monovalent monocyclic group having 3 to 50 ring atoms 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, a tetrahydrothiophenyl group, etc. 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.

[0422] In this specification, a cycloalkenyl group having 3 to 50 ring carbon atoms means a monovalent monocyclic group having 3 to 50 ring carbon atoms, which has at least one double bond in the ring but does not have aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, etc. In this specification, a cycloalkenylene group having 3 to 50 ring carbon atoms means a divalent group having the same structure as a cycloalkenyl group having 3 to 50 ring carbon atoms.

[0423] In the present specification, a heterocycloalkenyl group having 3 to 50 ring atoms is a monovalent monocyclic group having 3 to 50 ring atoms containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom, and having at least one double bond in the ring. Specific examples of heterocycloalkenyl groups having 3 to 50 ring atoms include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, and 2,3-dihydrothiophenyl groups. In the present specification, a heterocycloalkenylene group having 3 to 50 ring atoms means a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring atoms.

[0424] According to one embodiment, in the compound represented by the 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.

[0425] In this specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed with each other, the ring atoms are only carbon, and the entire molecule has non-aromaticity. In this specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0426] In this specification, a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed with each other and which contains, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S, and in which the entire molecule has non-aromatic properties. In this specification, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.

[0427] In this specification, the term "biphenylyl group" refers to a "phenyl group substituted with a phenyl group." The "biphenylyl group" belongs to the "substituted phenyl group" whose substituent is an "aryl group having 6 to 50 ring carbon atoms."

[0428] In the present 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".

[0429] In the compound represented by the general formula (21), the chemical bonds T1, T2, T3 and T4 are preferably single bonds.

[0430] 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 (Au), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm), and more preferably platinum (Pt) or iridium (Ir).

[0431] According to one embodiment, in the compound represented by the general formula (21), the rings CY1 to CY4 are each independently benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenophene, indole, benzoborole, benzophosphole, indene, benzosilole, benzogermole, benzothiophene, benzoselenophene, benzofuran, carbazole, dibenzoborole, 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, azabenzofuran, Azabenzoselenophene, azabenzofuran, azacarbazole, azadibenzoborole, azadibenzophosphole, azafluorene, azadibenzosilole, azadibenzogermol, azadibenzothiophene, azadibenzoselenophene, azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinolin In one embodiment, the aryl amine may be selected from the group consisting of phenylene, 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.

[0432] According to one embodiment, at least one of the CY1 ring and the CY2 ring in the general formula (211), at least one of the CY1 ring to the CY3 ring in the general formula (212), and at least one of the CY1 ring to the CY4 ring in the general formula (213) may be a carbene.

[0433] According to one embodiment, Y1 to Y4 in general formulas (211) to (213) may each independently be at least one selected from the group consisting of a single bond, a double bond, *aO-*b, *aS-*b, *aC(R5)(R6)-*b, and *aN(R5)-*b.

[0434] According to one embodiment, at least one of R1 and R2 in general formula (211), at least one of R1 to R3 in general formula (212), and at least one of R1 to R4 in general formula (213) may be an electron donating group.

[0435] For example, the electron-donating group may be a substituent selected from the group consisting of an iso-propyl group, a tert-butyl group, and the following general formulae (10-1) to (10-61).

[0436] [ka]

[0437] [ka]

[0438] In the above general formulae (10-1) to (10-61), * indicates the bonding position to the adjacent atom.

[0439] In this specification, a deuterium atom is represented as D in a chemical formula, and a protium atom is represented as H or is omitted. In this specification, a methyl group is 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.

[0440] According to one embodiment, at least one of R1 and R2 in the general formula (211) is a substituent other than hydrogen, and / or Y1 is *aN(R5)-*b, and R5 may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0441] According to one embodiment, at least one of R1 to R3 in the general formula (212) is a substituent other than hydrogen, and / or at least one of Y1 and Y2 is *aN(R5)-*b, and R5 may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0442] According to one embodiment, at least one of R1 to R4 in the general formula (213) is a substituent other than hydrogen, and / or at least one of Y1 to Y4 is *aN(R5)-*b, and R5 may be a substituted aryl group having 6 to 50 ring carbon atoms.

[0443] In the organic EL element according to the sixth embodiment, the light-emitting layer contains the compound M2 (the compound represented by the general formula (1) above), and therefore, according to the sixth embodiment, high efficiency of the organic EL element can be achieved. The organic EL element according to the sixth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0444] [Modification 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.

[0445] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be laminated. When the organic EL element has multiple light-emitting layers, at least one of the light-emitting layers may satisfy 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 a ground state. Furthermore, when the organic EL element has a plurality of 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 type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0446] In addition, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking 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 blocking layer is disposed in contact with the light-emitting layer on the cathode side, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) on the cathode side of the blocking layer. When the organic EL device includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer. In addition, when a blocking layer is disposed in contact with the light-emitting layer on the anode side, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) on the anode side of the blocking layer. When the organic EL device includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer. A barrier layer may be provided adjacent to the light-emitting layer to prevent the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.). The light emitting layer and the barrier layer are preferably in contact with each other.

[0447] In addition, the specific structure and shape in carrying out the present invention may be other structures and shapes within the scope of the invention in which the object of the present invention can be achieved. EXAMPLES

[0448] 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.

[0449] <Compound> The structures of the compounds represented by general formula (1) used in the production of the organic EL devices according to Examples 1 to 6 are shown below.

[0450] [ka]

[0451] [ka]

[0452] The structure of the comparative compound used in the production of the organic EL device according to Comparative Example 1 is shown below.

[0453] [ka]

[0454] The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 6 and Comparative Example 1 are shown below.

[0455] [ka]

[0456] [ka]

[0457] <Fabrication of Organic EL Device (1)> An organic EL device was prepared as follows and evaluated.

[0458] Example 1 On a glass substrate, a 100 nm thick silver alloy layer, APC (Ag-Pd-Cu) layer, and a 10 nm thick indium oxide-zinc oxide (IZO) layer were formed in that order by sputtering. This resulted in a conductive material layer consisting of an APC layer and an IZO layer. The APC layer is a light reflective layer, and the IZO layer is a transparent conductive layer. IZO is a registered trademark. Next, the conductive material layer consisting of the light-reflecting layer and the transparent conductive layer was patterned by etching using a resist pattern as a mask using normal lithography technology to form an anode. The substrate on which the lower electrode (anode) was formed was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. Next, on the lower electrode (anode), the compound HT-1 and the compound HA were co-deposited by vacuum deposition to form a hole injection layer having a thickness of 10 nm. The proportion of the compound HT-1 in the hole injection layer was 97% by mass, and the proportion of the compound HA was 3% by mass. Next, the compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 115 nm. Next, the compound EBL-1 was evaporated onto the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. The second hole transport layer may also be called an electron blocking layer. Next, on the second hole transport layer, 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 to form an emission layer having a thickness of 31 nm. The ratio of compound Matrix-1 in this emission layer was 73.8 mass%, the ratio of compound TADF1 was 25 mass%, and the ratio of compound BD-1 was 1.2 mass%. Next, the compound HBL-1 was evaporated onto the light-emitting layer to form a first electron transport layer having a thickness of 5 nm. The first electron transport layer may also be called a hole blocking layer. On the first electron transport layer, the compound ET-1 and the compound Liq were co-deposited to form a second electron transport layer having a thickness of 31 nm. The ratio of the compound ET-1 in the second electron transport layer was set to 50 mass %, and the ratio of the compound Liq was set to 50 mass %. Note that Liq is an abbreviation for (8-quinolinolato)lithium. Ytterbium (Yb) was evaporated onto the second electron transport layer to form an electron injection layer having a thickness of 1 nm. On the electron injection layer, Mg and Ag were evaporated in a mixture ratio (mass %) of 10:90 to form a 13 nm-thick upper electrode (cathode) made of a semi-transparent MgAg alloy. A film of compound Cap-1 was formed 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 type organic EL element according to Example 1 was produced. The device configuration of Example 1 is shown in schematic form 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) In the above element configurations, the numbers in parentheses indicate film thicknesses (unit: nm). Regarding the element configuration of Example 1, the percentages (97%:3%) in parentheses indicate the ratio (mass%) of the compound HT-1 and the compound HA in the hole injection layer, the percentages (73.8:25%:1.2%) indicate the ratio (mass%) of the compound M1 (compound Matrix-1), the compound M2 (compound TADF1), and the compound M3 (compound BD-1) in the light-emitting layer, the percentages (50%:50%) indicate the ratio (mass%) of the compound ET-1 and Liq in the second electron transport layer, and the percentages (10%:90%) indicate the mixing ratio (mass%) of Mg and Ag in the upper electrode (cathode). The same notations are used below.

[0459] (Examples 2 to 6) The organic EL devices of Examples 2 to 6 were produced 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 compounds shown in Table 1.

[0460] Comparative Example 1 The organic EL device of Comparative Example 1 was produced 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.

[0461] <Evaluation of organic EL elements> The organic EL devices thus fabricated were evaluated as follows. The evaluation results are shown in Table 1.

[0462] (L / J / CIEy) The organic EL device fabricated had a current density of 10 mA / cm 2 The spectral radiance spectrum when a voltage was applied so that the spectral radiance spectrum was measured using a spectroradiometer CS-1000 (manufactured by Konica Minolta, Inc.) The chromaticity CIEx, CIEy, and current efficiency L / J (unit: cd / A) were calculated from the obtained spectral radiance spectrum. The "L / J / CIEy" value was calculated by dividing the current efficiency L / J by the CIEy. The "L / J / CIEy" value is sometimes called the Blue Index (BI). In this evaluation, the Blue Index (BI) value was used as an index of luminous efficiency.

[0463] The "BI (relative value)" (unit: %) shown in Table 1 was calculated based on the BI value of each example (Examples 1 to 6 and Comparative Example 1) and the following formula (Number X1). BI (relative value) = (BI of each example / BI of Comparative Example 1) x 100 ... (number X1)

[0464] [Table 1]

[0465] In Examples 1 to 6, the compounds TADF1 to 6 used as sensitizing materials have a structure in which an azine ring having a 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 compound Ref-1 used as a sensitizing material in Comparative Example 1 is a compound in which the azacarbazolyl groups in the compounds TADF1 to 4 are each replaced with a carbazolyl group. The organic EL elements of Examples 1 to 6 emitted light with higher efficiency than the organic EL element of Comparative Example 1.

[0466] <Compound evaluation> The compounds were evaluated as follows.

[0467] (Lowest excited singlet energy S1) A 10μmol / 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 (300K). 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 the tangent line and the horizontal axis was substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge The absorption spectrum measuring device used was a spectrophotometer manufactured by Hitachi (device name: U3310).

[0468] The tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction towards 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 at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the falling edge on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0469] (Energy gap T at 77[K] 77K ) The compound to be measured was 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 was placed in a quartz cell to prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), a tangent was drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent and the horizontal axis was determined. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K It was decided. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0470] 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 of 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 the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. The phosphorescence was measured using a Hitachi High-Technologies Corporation F-4500 spectrofluorophotometer.

[0471] (ΔST) The lowest excited singlet energy S1 and energy gap T measured 77K Based on the value of ΔST=S1-T 77K was calculated. It was confirmed that ΔST was less than 0.3 eV for the compounds TADF1 to TADF6 and the comparative compound Ref-1.

[0472] (Delayed fluorescence of compounds) The delayed fluorescence was confirmed by measuring the 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, and then sealed in a cell with a lid under an argon atmosphere to prepare an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength absorbed by the compound TADF1, there are prompt luminescence (instantaneous luminescence) that is observed immediately from the excited state, and delayed luminescence (delayed luminescence) that is not observed immediately after the excitation and is observed later. In this embodiment, delayed fluorescent luminescence means that the amount of delayed luminescence (delayed luminescence) is 5% or more of the amount of prompt luminescence (instantaneous luminescence). Specifically, when the amount of prompt luminescence (instantaneous luminescence) is X P and the amount of delay light emission is X D When X D / X P This means that the value is 0.05 or more. The amount and ratio of prompt luminescence and delayed luminescence 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 amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2. Compounds TADF2 to TADF6 and comparative compound Ref-1 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 relative to the amount of prompt luminescence (prompt luminescence) for the compounds TADF1 to TADF6 and the comparative compound Ref-1. D / X P The value was 0.05 or higher.

[0473] (Fluorescence emission maximum peak wavelength λ FL and emission spectrum half width FWHM) The compound to be measured was dissolved in toluene and diluted with 5.0×10 -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 "Spectrofluorophotometer FP-8300" (manufactured by JASCO Corporation). FL (unit: nm) and emission spectrum half width FWHM (unit: nm) were measured. Maximum peak wavelength λ of compound BD-1 FL The wavelength was 455 nm, and the emission spectrum half width FWHM was 23 nm.

[0474] <Synthesis Example> 1. Synthesis of compound TADF1 (1) Synthesis of compound (1-2)

[0475] [ka]

[0476] Under an argon atmosphere, compound (1-1) (5.00 g, 15.5 mmol), bis(pinacolato)diboron (4.32 g, 17.0 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.227 g, 0.310 mmol), potassium acetate (2.28 g, 23.3 mmol), and 1,4-dioxane (50 mL) were added and heated and stirred at 90°C for 18 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (3.44 g, 60% yield). 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.

[0477] (2) Synthesis of compound TADF1

[0478] [ka]

[0479] Under an argon atmosphere, compound (1-2) (2.41 g, 6.51 mmol), compound (1-3) (2.11 g, 5.92 mmol), tetrakistriphenylphosphine palladium (0.205 g, 0.178 mmol), 2 M aqueous sodium carbonate solution (10 mL), and 1,4-dioxane (60 mL) were added and heated and stirred at 90°C for 15 hours. After the reaction was completed, the reaction product 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 (2.71 g, yield 81%). The obtained solid was the target compound TADF1, and as a result of mass spectrometry, it was found that m / e=564 for a molecular weight of 564.

[0480] 2. Synthesis of Compound TADF2 (1) Synthesis of compound (2-2)

[0481] [ka]

[0482] Under an argon atmosphere, compound (2-1) (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 and stirred at 90°C for 20 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (2.99 g, 58% yield). The obtained solid was the target compound (2-2), and as a result of mass spectrometry analysis, it was found that m / e=370 for a molecular weight of 370.

[0483] (2) Synthesis of compound TADF2

[0484] [ka]

[0485] Under an argon atmosphere, compound (2-2) (2.69 g, 7.27 mmol), compound (1-3) (2.36 g, 6.60 mmol), tetrakistriphenylphosphine palladium (0.229 g, 0.198 mmol), 2 M aqueous sodium carbonate solution (11 mL), and 1,4-dioxane (66 mL) were added and heated and stirred at 90°C for 17 hours. After the reaction was completed, the reaction product 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 (2.65 g, 71% yield). The obtained solid was the target compound TADF2, and as a result of mass spectrometry, it was found that m / e=564 for a molecular weight of 564.

[0486] 3. Synthesis of Compound TADF3 (1) Synthesis of compound (3-2)

[0487] [ka]

[0488] Under an argon atmosphere, compound (3-1) (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 and stirred at 90°C for 18 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (3.46 g, yield 65%). The obtained solid was the target compound (3-2), and as a result of mass spectrometry analysis, it was found that m / e=370 for a molecular weight of 370.

[0489] (2) Synthesis of compound TADF3

[0490] [ka]

[0491] Under an argon atmosphere, compound (3-2) (3.33 g, 8.99 mmol), compound (1-3) (2.92 g, 8.18 mmol), tetrakistriphenylphosphine palladium (0.283 g, 0.245 mmol), 2 M aqueous sodium carbonate solution (13 mL), and 1,4-dioxane (80 mL) were added and heated and stirred at 90°C for 18 hours. After the reaction was completed, the reaction product 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 (3.32 g, 72% yield). The obtained solid was the target compound TADF3, and as a result of mass spectrometry, it was found that m / e = 564 for a molecular weight of 564.

[0492] 4. Synthesis of Compound TADF4 (1) Synthesis of compound (4-2)

[0493] [ka]

[0494] Under an argon atmosphere, compound (4-1) (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 and stirred at 90°C for 20 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (3.93 g, yield 66%). The obtained solid was the target compound (4-2), and as a result of mass spectrometry analysis, it was found that m / e=370 for a molecular weight of 370.

[0495] (2) Synthesis of compound TADF4

[0496] TIFF2025021083000135.tif56165

[0497] Under an argon atmosphere, compound (4-2) (2.97 g, 8.02 mmol), compound (1-3) (2.60 g, 7.29 mmol), tetrakistriphenylphosphine palladium (0.253 g, 0.219 mmol), 2 M aqueous sodium carbonate solution (12 mL), and 1,4-dioxane (73 mL) were added and heated and stirred at 90°C for 18 hours. After the reaction was completed, the reaction product 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 (3.25 g, 79% yield). The obtained solid was the target compound TADF4, and as a result of mass spectrometry, it was found that m / e=564 for a molecular weight of 564.

[0498] 5. Synthesis of Compound TADF5 (1) Synthesis of compound (5-2)

[0499] [ka]

[0500] Under an argon atmosphere, 1-bromo-2,3-difluorobenzene (5.35 g, 27.7 mmol), compound (5-1) (10.3 g, 61.0 mmol), cesium carbonate (22.6 g, 69.3 mmol), and N,N-dimethylformamide (200 mL) were added and heated and stirred at 150° C. for 10 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (8.55 g, yield 63%). The obtained solid was the target compound (5-2), and as a result of mass spectrometry analysis, it was found that m / e=489 for a molecular weight of 489.

[0501] (2) Synthesis of compound (5-3)

[0502] [ka]

[0503] Under an argon atmosphere, compound (5-2) (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 and stirred at 90°C for 24 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (3.08 g, yield 61%). The obtained solid was the target compound (5-3), and as a result of mass spectrometry analysis, it was found that m / e=536 for a molecular weight of 536.

[0504] (3) Synthesis of compound TADF5

[0505] [ka]

[0506] Under an argon atmosphere, compound (5-3) (2.61 g, 4.87 mmol), compound (1-3) (1.58 g, 4.42 mmol), tetrakistriphenylphosphine palladium (0.153 g, 0.133 mmol), 2 M aqueous sodium carbonate solution (7 mL), and 1,4-dioxane (44 mL) were added and heated and stirred at 90°C for 18 hours. After the reaction was completed, the reaction product 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 (1.91 g, 59% yield). The obtained solid was the target compound TADF5, and as a result of mass spectrometry, it was found that m / e=730 for a molecular weight of 730.

[0507] 6. Synthesis of Compound TADF6 (1) Synthesis of compound (6-2)

[0508] [ka]

[0509] Under an argon atmosphere, 1-bromo-2,3-difluorobenzene (4.97 g, 25.8 mmol), compound (6-1) (9.53 g, 56.7 mmol), cesium carbonate (21.0 g, 64.4 mmol), and N,N-dimethylformamide (200 mL) were added and heated and stirred at 150° C. for 12 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (7.31 g, 58% yield). The obtained solid was the target compound (6-2), and as a result of mass spectrometry analysis, it was found that m / e=489 for a molecular weight of 489.

[0510] (2) Synthesis of compound (6-3)

[0511] [ka]

[0512] Under an argon atmosphere, compound (6-2) (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 and stirred at 90°C for 21 hours. After the reaction was completed, water and ethyl acetate were added to the reaction product, the organic layer was extracted, and the crude product obtained by distilling off the solvent was purified by column chromatography to obtain a white solid (2.46 g, 57% yield). The obtained solid was the target compound (6-3), and as a result of mass spectrometry analysis, it was found that m / e=819 for a molecular weight of 819.

[0513] (3) Synthesis of compound TADF6

[0514] [ka]

[0515] Under an argon atmosphere, compound (6-3) (2.12 g, 3.95 mmol), compound (1-3) (1.28 g, 3.59 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 and stirred at 90°C for 19 hours. After the reaction was completed, the reaction product 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 (1.73 g, yield 66%). The obtained solid was the target compound TADF6, and as a result of mass spectrometry, it was found that m / e=730 for a molecular weight of 730. [Explanation of symbols]

[0516] Reference Signs List 1: organic electroluminescence element, 10: organic layer, 2: substrate, 3: anode, 4: cathode, 5: light-emitting layer, 6: hole injection layer, 7: hole transport layer, 8: electron transport layer, 9: electron injection layer.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 【Chemistry 2】 (In the general formula (1), X １ ~X ４ are each independently a nitrogen atom or CRx; However, X １ ~X ４ At least one of the groups is a nitrogen atom, When a plurality of Rx's are present, the plurality of Rx's are the same or different from each other, Y １ ~Y ３ are each independently a nitrogen atom or CH; However, Y １ ~Y ３ two or more of are nitrogen atoms, Ring A, ring B and ring C each independently represent 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, Z １ and Z ２ Each independently represents a single bond, C(R １ ) (R ２ ), N.R. ３ , an oxygen atom, or a sulfur atom; Ar １ teeth, Hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A group represented by the general formula (2), Ar ２ teeth, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A group represented by the general formula (3), m is 1, 2, 3, 4 or 5; n is 0, 1, 2, 3 or 4; m+n=5, When m is 2, 3, 4 or 5, Multiple X's １ are identical or different from each other, Multiple X's ２ are identical or different from each other, Multiple X's ３ are identical or different from each other, Multiple X's ４ are identical or different from each other, The A rings are the same or different from each other, Multiple Zs １ are identical or different from each other, When n is 2, 3 or 4, A plurality of Ar １ are identical or different from each other, *1 and *2 indicate the bonding positions to the benzene ring, 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 Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, Ar １ is a group represented by the general formula (2), R １１ ~R １８ and R ３Ａ one of them is a single bond to the benzene ring in the general formula (1), In the general formula (3), W is C(R ２１Ａ ) (R ２２Ａ ), an oxygen atom, or a sulfur atom; R ２１ ~R ２８ Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, Ar ２ is a group represented by the general formula (3), R ２１ ~R ２８ In the general formula (1), one of １ and Y ３ is a single bond to a carbon atom between Rx, R １ , R ２ , R ３ , R １Ａ , R ２Ａ , R ２１Ａ , R ２２Ａ and the Y １ and Y ３ R is not a single bond to a carbon atom between ３Ａ , R １１ ~R １８ and R ２１ ~R ２８ are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) a group represented by -O-(R ９０４ ) a group represented by -S-(R ９０５ ) a group represented by -N(R ９０６ ) (R ９０７ ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. (In the compound represented by the general formula (1), R ９０１ ~R ９０７ are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９０１ When there are multiple R ９０１ are the same or different from each other, R ９０２ When there are multiple R ９０２ are the same or different from each other, R ９０３ When there are multiple R ９０３ are the same or different from each other, R ９０４ When there are multiple R ９０４ are the same or different from each other, R ９０５ When there are multiple R ９０５ are the same or different from each other, R ９０６ When there are multiple R ９０６ are the same or different from each other, R ９０７ When there are multiple R ９０７ are the same or different from each other.)

2. Z １ and Z ２ is a single bond, The compound of claim 1.

3. Ring A, ring B and ring C each independently represent a substituted or unsubstituted benzene ring, or A substituted or unsubstituted dibenzothiophene ring. A compound according to claim 1 or claim 2.

4. X １ ~X ３ is a nitrogen atom, and X is not a nitrogen atom. １ ~X ４ is CRx; A compound according to any one of claims 1 to 3.

5. X ２ Or X ４ is a nitrogen atom, and X is not a nitrogen atom １ ~X ４ is CRx; A compound according to any one of claims 1 to 4.

6. Y ２ and Y ３ are nitrogen atoms, and Y １ is CH, or Y １ ~Y ３ Three of these are nitrogen atoms. A compound according to any one of claims 1 to 5.

7. Y １ ~Y ３ Three of these are nitrogen atoms. A compound according to any one of claims 1 to 6.

8. Ar １ teeth, A hydrogen atom, or 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; A compound according to any one of claims 1 to 7.

9. Ar ２ teeth, a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group; A compound according to any one of claims 1 to 8.

10. In the compound represented by the general formula (1), the partial structure represented by the following general formula (1A) is each independently a group represented by any one of the following general formulas (11A) to (14A): A compound according to any one of claims 1 to 9. 【Chemistry 3】 (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 is synonymous with 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). 【Chemistry 4】 (In the general formulas (11A) to (14A), R ３１１ ~R ３１８ Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ３１１ ~R ３１８ are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) a group represented by -O-(R ９０４ ) a group represented by -S-(R ９０５ ) a group represented by -N(R ９０６ ) (R ９０７ ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R in the general formulae (11A) to (14A) ９０１ ~R ９０７ are R in the general formula (1), ９０１ ~R ９０７ is synonymous with *1 has the same meaning as *1 in the general formula (1A).

11. In the compound represented by the general formula (1), the partial structure represented by the following general formula (1B) is a group represented by any one of the following general formulas (11B) to (13B): A compound according to any one of claims 1 to 10. 【Chemistry 5】 (In the general formula (1B), ring B, ring C and Z ２ respectively represent ring B, ring C and Z in the general formula (1). ２ and *3 represents the Y ２ and Y ３ This indicates the bond position to the carbon atom between 【Chemistry 6】 (In the general formulae (11B) to (13B), R ５１１ ~R ５１４ and R ５２０ Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R ６１１ ~R ６１４ and R ６２０ Among the groups of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Multiple R ５２０ are the same or different, Multiple R ６２０ are the same or different, Ar ３ teeth, 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 does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ５１１ ~R ５１４ , R ５２０ , R ６１１ ~R ６１４ and R ６２０ are each independently Hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９０１ ) (R ９０２ ) (R ９０３ ) a group represented by -O-(R ９０４ ) a group represented by -S-(R ９０５ ) a group represented by -N(R ９０６ ) (R ９０７ ) a group represented by Halogen atoms, Cyano group, Nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R in the general formulae (11B) to (13B) ９０１ ~R ９０７ are R in the general formula (1), ９０１ ~R ９０７ is synonymous with *3 has the same meaning as *3 in the general formula (1B).

12. m is 1; A compound according to any one of claims 1 to 11.

13. Rx, R １ , R ２ , R ３ , R １Ａ , R ２Ａ , R ３Ａ , R ２１Ａ , R ２２Ａ , R １１ ~R １８ and R ２１ ~R ２８ are each independently 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. A compound according to any one of claims 1 to 12.

14. A material for an organic electroluminescence device, comprising the compound according to claim 1 .

15. A cathode; An anode; an organic layer disposed between the cathode and the anode; The organic layer comprises a compound according to any one of claims 1 to 13 as compound M2, Organic electroluminescent element.

16. The organic layer has at least one light-emitting layer, The light-emitting layer comprises the compound M2; The organic electroluminescence device according to claim 15 .

17. The lowest excited singlet energy S of the compound M2 １ (M2) and the energy gap T at 77[K] ７７Ｋ The difference ΔST(M2) between (M2) satisfies the relationship of the following formula (Formula 1): The organic electroluminescence device according to claim 15 or 16. ΔST(M2) = S １ (M2) - T( ７７Ｋ (M2) < 0.3 eV … (Equation 1)

18. The light-emitting layer contains the compound M2 as a sensitizing material. The organic electroluminescence device according to any one of claims 15 to 17.

19. The sensitizing material is a delayed fluorescent compound. The organic electroluminescence device according to claim 18.

20. The light-emitting layer further contains a fluorescent material, The fluorescent material is a compound represented by the following general formula (41): The organic electroluminescence device according to any one of claims 16 to 19. 【Chemistry 7】 (In the general formula (41), Ring a, ring b and ring c each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring 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 are each independently by combining with the ring a, ring b or ring c to form a substituted or unsubstituted monocycle, or not bonded to the ring a, ring b, or ring c; R ４１ and R ４２ teeth, joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R ４３ and R ４４ teeth, joined together to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. ４０ ~R ４４ 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, -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, R ４５ teeth, 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 identical or different from each other, R ４１ When there are multiple R ４１ are identical or different from each other, R ４２ When there are multiple R ４２ are identical or different from each other, R ４３ When there are multiple R ４３ are identical or different from each other, R ４４ When there are multiple R ４４ are identical or different from each other, R ４５ When there are multiple R ４５ are the same or different from each other.)

21. The light-emitting layer contains the compound M2 as a host material. The organic electroluminescence device according to claim 16 or 17.

22. The host material is a delayed fluorescent compound. The organic electroluminescence device according to claim 21 .

23. The light-emitting layer does not contain a metal complex. The organic electroluminescence device according to any one of claims 16 to 22.

24. The light-emitting layer does not contain a phosphorescent material. The organic electroluminescence device according to any one of claims 16 to 23.

25. a hole transport layer between the anode and the light emitting layer; The organic electroluminescence device according to any one of claims 16 to 24.

26. an electron transport layer between the cathode and the light emitting layer; The organic electroluminescence device according to any one of claims 16 to 25.

27. An electronic device comprising the organic electroluminescence element according to any one of claims 15 to 26.

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