Compound, organic electroluminescent element, and electronic device

Abstract

To provide an organic electroluminescent element having improved lifetime.SOLUTION: An organic electroluminescence device, comprises an anode, a cathode, and an emitting region disposed between the anode and the cathode, wherein the emitting region includes a first emitting layer and a second emitting layer, and the first emitting layer contains a first compound represented by a formula (1A) below.SELECTED DRAWING: Figure 1

Description

[Technical Field]

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

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

[0003] [Patent Document 1] International Publication No. 2021 / 132535 [Patent Document 2] Special Publication No. 2013-509363 Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a compound capable of improving the life of an organic electroluminescence element, an organic electroluminescence element containing the compound, and an electronic device equipped with the organic electroluminescence element. Another object of the present invention is to provide an organic electroluminescent element with an improved lifespan, and an electronic device incorporating the organic electroluminescent element. [Means for solving the problem]

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

[0006] (In the general formula (1A), R4 to R8 and R 10 ~R 12 one of which is a group represented by general formula (1B) above, R1 to R3, R9, and R4 to R8 and R other than the group represented by the general formula (1B) 10 ~R 12 are each independently, 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 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 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 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 902 , R 903 , R 904 , R 905 , R 801 , and R 802 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 R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, In the general formula (1B), n1 is an integer of 0 or 1 or more, When n1 is an integer equal to or greater than 1, L1 is an unsubstituted arylene group having 6 to 50 ring carbon atoms; an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, when unsubstituted, the arylene group having 6 to 50 ring carbon atoms is not a fused ring, but is When two or more L1s are present, the two or more L1s are the same or different from each other, Ar1 is an aryl group having four or more substituted or unsubstituted rings condensed together, or a heterocyclic group having four or more fused substituted or unsubstituted rings, * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), However, R1 to R 12 and when at least one of L1 and Ar1 in the general formula (1B) has at least one deuterium atom and only L1 has a deuterium atom, the deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in the general formula (1A) among the rings constituting L1.

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

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

[0009] [ka]

[0010] (In the general formula (100A), R 101 ~R 112 one of which is a group represented by general formula (100B) R other than the group represented by general formula (100B) 101 ~R 112 are each independently, 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 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 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 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 902 , R 903 , R 904 , R 905 , R 801 , and R 802 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 R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, In the general formula (100B), n101 is an integer of 0 or 1 or more, L when n101 is an integer greater than or equal to 1 101 teeth, an unsubstituted arylene group having 6 to 50 ring carbon atoms; an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, when unsubstituted, the arylene group having 6 to 50 ring carbon atoms is not a fused ring, but is L 101 If there are two or more, there are two or more L 101 are identical to or different from each other, Ar 101 teeth, an aryl group in which three or more substituted or unsubstituted rings are condensed, or a heterocyclic group in which three or more substituted or unsubstituted rings are condensed, * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), However, R in the general formula (100A) 101 ~R 112 and L in the general formula (100B). 101 and Ar 101 At least one of the groups has at least one deuterium atom, and L 101 If only L has a deuterium atom, 101 Among the rings constituting the formula (100A), a deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in the formula (100A).

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

[0012] According to one embodiment of the present invention, it is possible to provide a compound capable of improving the lifetime of an organic electroluminescence element, an organic electroluminescence element including the compound, and an electronic device equipped with the organic electroluminescence element. According to one embodiment of the present invention, an organic electroluminescence element with an improved lifetime and an electronic device equipped with the organic electroluminescence element can be provided. [Brief explanation of the drawings]

[0013] [Figure 1] 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to an embodiment of the present invention. [Figure 2] FIG. 2 is a diagram showing a schematic configuration of another example of an organic electroluminescence element according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

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

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

[0016] In this specification, the number of ring carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Furthermore, for example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9'-spirobifluorenyl group has 25 ring carbon atoms. Furthermore, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted with an alkyl group is 10.

[0017] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, or a ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms terminating the bonds of atoms constituting the ring) and atoms contained in the substituent when the ring is substituted with a substituent are not included in the number of ring atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to 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. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring, so the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0018] In this specification, the "number of carbon atoms XX to YY" in the expression "substituted or unsubstituted ZZ group having carbon atoms XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

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

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

[0021] "Substituents described herein" The substituents described in this specification will be explained below.

[0022] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. Unless otherwise specified in this specification, the "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. Unless otherwise specified 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. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0023] "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent, and examples of the substituted aryl group in the specific example group G1A below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.

[0024] Unsubstituted aryl groups (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl groups, 9,9'-spirobifluorenyl group, benzofluorenyl groups, dibenzofluorenyl groups, fluoranthenyl group, benzofluoranthenyl group, perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0025] [ka]

[0026] [ka]

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

[0028] "Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which a hydrogen atom of the "unsubstituted heterocyclic group" in the specific example group G2A below is replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are also included. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent.

[0029] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0030] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

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

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

[0033] 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, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0034] Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0035] [ka]

[0036] [ka]

[0037] In the general formulae (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0038] Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1): a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

[0039] 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].

[0040] 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].

[0041] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4):

[0042] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A a hydrogen atom bonded to a nitrogen atom when at least one of A and Y Aor more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

[0043] "Substituted or unsubstituted alkyl groups" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described herein include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when simply referring to an "alkyl group," both an "unsubstituted alkyl group" and a "substituted alkyl group" are included. The term "substituted alkyl group" refers to an "unsubstituted alkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Note that the examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent.

[0044] 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.

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

[0046] "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described herein include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (Here, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to an "unsubstituted alkenyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). The examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of the alkenyl group itself has been further replaced with a substituent, and groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of a substituent has been further replaced with a substituent.

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

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

[0049] "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.

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

[0051] "Substituted or unsubstituted cycloalkyl groups" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described herein include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to an "unsubstituted cycloalkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in the "substituted cycloalkyl group" of specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself have been replaced with a substituent, and a group in the "substituted cycloalkyl group" of specific example group G6B in which a hydrogen atom of a substituent has been further replaced with a substituent.

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

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

[0054] -Si(R 901 )(R 902 )(R 903 ) a group represented by -Si(R) 901 )(R 902 )(R 903 Specific examples (specific example group G7) of the group represented by -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here, G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0055] -O-(R 904 ) a group represented by -O-(R904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0056] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

[0057] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: where: G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0058] "Halogen atoms" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0059] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The term "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include the examples of the above-mentioned "alkyl group" (specific example group G3) in which one or more hydrogen atoms are replaced with a fluorine atom.

[0060] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. The term "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include the examples of the above-mentioned "alkyl groups" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

[0061] "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.

[0062] "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.

[0063] "Substituted or unsubstituted aryloxy group" A specific example of the "substituted or unsubstituted aryloxy group" described in this specification is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. 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.

[0064] "Substituted or unsubstituted arylthio group" A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in specific example group G1. 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.

[0065] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0066] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group," and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.

[0067] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or the like.

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

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

[0070] [ka]

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

[0072] [ka]

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

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

[0075] [ka]

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

[0077] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, and the like.

[0078] "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples 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.

[0079] "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0080] "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group." Specific examples 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.

[0081] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-42) to (TEMP-68).

[0082] [ka]

[0083] [ka]

[0084] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0085] [ka]

[0086] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulae (TEMP-53) to (TEMP-62), * represents a bonding position.

[0087] [ka]

[0088] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0089] Unless otherwise specified in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the groups represented by the following general formulae (TEMP-69) to (TEMP-102).

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

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

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

[0101] [ka]

[0102] For example, R921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," one pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.

[0103] The above "one or more pairs" means that two or more pairs of adjacent two or more groups may simultaneously form a ring. For example, R 921 and R 922 and are bonded to each other to form ring Q A At the same time, R 925 and R 926 and are bonded to each other to form ring Q B When the anthracene compound represented by the general formula (TEMP-103) is formed, the anthracene compound represented by the general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0104] [ka]

[0105] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105): A and Ring Q C is R 922 Share.

[0106] [ka]

[0107] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one pair of adjacent two" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" may form a saturated ring or an unsaturated ring. For example, in the case of the ring Q formed in the general formula (TEMP-104), A and Ring Q B are "monocyclic rings" or "fused rings", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0108] 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 "forming a ring" means that a ring is formed only with a plurality of atoms of the main skeleton, or with a plurality of atoms of the main skeleton and one or more optional elements. For example, R 921 and R 922 and are bonded 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 a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by

[0109] Here, unless otherwise specified in this 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 carbon or nitrogen), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" is preferably a benzene ring. Unless otherwise specified herein, the "unsaturated ring" is preferably a benzene ring. When "one or more pairs of adjacent two or more groups" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more groups combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0110] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0111] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and a group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms, where R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, 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 to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R 903 If there are two or more, there are two or more R903 are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0112] In one embodiment, the substituents in the "substituted or unsubstituted" are: 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.

[0113] In one embodiment, the substituents in the "substituted or unsubstituted" are: 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.

[0114] Specific examples of each group of the above optional substituents are the specific examples of the substituents described above in the section "Substituents described in this specification."

[0115] Unless otherwise specified in this specification, any adjacent substituents may be bonded to each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. Unless otherwise specified in this specification, any optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

[0116] In this specification, a numerical range expressed using "AA to BB" means a range that includes the number AA written before "AA to BB" as the lower limit and the number BB written after "AA to BB" as the upper limit.

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

[0118] [ka]

[0119] (In the general formula (100A), R 101 ~R 112 one of which is a group represented by general formula (100B) R other than the group represented by general formula (100B) 101 ~R 112 are each independently, 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 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 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 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 902 , R 903 , R 904 , R 905 , R 801 , and R 802 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 R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R802 If there are multiple R 802 are the same or different from each other, In the general formula (100B), n101 is an integer of 0 or 1 or more, L when n101 is an integer greater than or equal to 1 101 teeth, an unsubstituted arylene group having 6 to 50 ring carbon atoms; an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, when unsubstituted, the arylene group having 6 to 50 ring carbon atoms is not a fused ring, but is L 101 If there are two or more, there are two or more L 101 are identical to or different from each other, Ar 101 teeth, an aryl group in which three or more substituted or unsubstituted rings are condensed, or a heterocyclic group in which three or more substituted or unsubstituted rings are condensed, * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), However, R in the general formula (100A) 101 ~R 112 and L in the general formula (100B). 101 and Ar 101 At least one of the groups has at least one deuterium atom, and L 101 If only L has a deuterium atom, 101 Among the rings constituting the formula (100A), a deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in the formula (100A).

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

[0121] In the compound according to this embodiment, L 101When L is an arylene group, the arylene group is an unsubstituted arylene group having 6 to 50 ring carbon atoms that is not a fused ring, or an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are fused. 101 In the above formula, for example, a divalent group derived from biphenyl and a divalent group derived from terphenyl correspond to an "unsubstituted arylene group having 6 to 50 ring carbon atoms", and a divalent group derived from naphthalene corresponds to an "arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed". The same applies to L1 in general formula (1A) described below.

[0122] In addition, in the compound according to this embodiment, L 101 If only one has a deuterium atom, then "L 101 The "ring directly bonded to the benz[a]anthracene ring in the general formula (100A) among the rings constituting the formula (100A)" includes, for example, L 101 is a biphenyl group represented by the following general formula (101x), and *a is the bonding position to the benz[a]anthracene ring, it corresponds to ring A. In addition, in the compound according to this embodiment, L 101 If only one has a deuterium atom, then "L 101 The phrase "a deuterium atom is bonded to the ring directly bonded to the benz[a]anthracene ring in the general formula (100A) among the rings constituting the formula" means, for example, L 101 is a biphenyl group represented by the following general formula (101x), and *a is the bonding position to the benz[a]anthracene ring, this means that a deuterium atom is bonded to at least one of *A1 to *A3 in ring A. The same applies to L1 in general formula (1A) described below.

[0123] [ka]

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

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

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

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

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

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

[0130] [ka]

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

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

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

[0134] [ka]

[0135] (In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), n1 is 0, 1, 2, or 3; When n1 is 1, 2, or 3, L1 is an unsubstituted arylene group having 6 to 50 ring carbon atoms; an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, when unsubstituted, the arylene group having 6 to 50 ring carbon atoms is not a fused ring, but is When two or more L1s are present, the two or more L1s are the same or different from each other, In the general formula (1B-1), R 51 ~R 54 , R 57 , and R 61 ~R 64 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring51 ~R 54 , R 57 , and R 61 ~R 64 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, * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), In the general formula (1B-2), R 51 ~R 53 , R 56 , R 57 , and R 71 ~R 74 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 51 ~R 53 , R56 , R 57 , and R 71 ~R 74 are each independently R in the general formula (1B-1). 51 ~R 54 , R 57 , and R 61 ~R 64 is synonymous with * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), In the general formula (1B-3), R 51 ~R 55 , and R 81 ~R 84 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 51 ~R 55 , and R 81 ~R 84 are each independently R in the general formula (1B-1). 51 ~R 54 , R 57 , and R 61 ~R 64 is synonymous with * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), In the general formula (1D), R 21 ~R 30 one of which indicates a bonding position to the benz[a]anthracene ring in the general formula (100A), and R in the general formula (1D) which is not the bonding position 21 ~R 30 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (1D) which is not at a bonding position with the benz[a]anthracene ring in the general formula (100A), does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring 21 ~R 30 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, In the groups represented by the general formulae (1B-1), (1B-2), (1B-3), and (1D), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , and R 907 are each independently, 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 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.)

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

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

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

[0139] In the compound according to this embodiment, at least R 101 ~R112 It is also preferred that either of the above is a deuterium atom.

[0140] In the compound according to this embodiment, R 105 , R 106 , R 107 , R 108 , R 111 , or R 112 is also preferably a group represented by the general formula (100B). In the compound according to this embodiment, R 106 , R 107 , R 111 , or R 112 is also preferably a group represented by the general formula (100B). In the compound according to this embodiment, R 111 is also preferably a group represented by the general formula (100B). R is the site where the HOMO and LUMO have higher electron density or the singlet energy S1 is smaller. 105 , R 106 , R 107 , R 108 , R 111 , or R 112 When is a group represented by the general formula (100B), the excitation resistance of the compound according to this embodiment is likely to be improved, and the effect of extending the life of the organic EL device is likely to be obtained.

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

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

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

[0144] [ka]

[0145] (In the general formula (1A), R4 to R8 and R 10 ~R 12 one of which is a group represented by general formula (1B) above, R1 to R3, R9, and R4 to R8 and R other than the group represented by the general formula (1B) 10 ~R 12 are each independently, 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 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 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 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 902 , R 903 , R 904 , R 905 , R801 , and R 802 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 R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, In the general formula (1B), n1 is an integer of 0 or 1 or more, When n1 is an integer equal to or greater than 1, L1 is an unsubstituted arylene group having 6 to 50 ring carbon atoms; an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, when unsubstituted, the arylene group having 6 to 50 ring carbon atoms is not a fused ring, but is When two or more L1s are present, the two or more L1s are the same or different from each other, Ar1 is an aryl group having four or more substituted or unsubstituted rings condensed together, or a heterocyclic group having four or more fused substituted or unsubstituted rings, * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), However, R1 to R 12 and when at least one of L1 and Ar1 in the general formula (1B) has at least one deuterium atom and only L1 has a deuterium atom, the deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in the general formula (1A) among the rings constituting L1.

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

[0147] In the compound according to this embodiment, when n1 is an integer of 1 or more, L1 is also preferably a substituted or unsubstituted arylene group having 6 to 13 ring carbon atoms.

[0148] In the compound according to this embodiment, the substituent on L1 is preferably an aryl group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 16 ring atoms, more preferably an aryl group having 6 to 13 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 12 ring atoms, and more preferably a phenyl group or a naphthyl group.

[0149] In the compounds according to this embodiment, it is also preferred that L1 is unsubstituted.

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

[0151] [ka]

[0152] In the compound according to this embodiment, n1 is also preferably 0. That is, it is also preferable that Ar1 and the benz[a]anthracene ring in the general formula (1A) are directly bonded to each other.

[0153] In the compound according to this embodiment, Ar1 is also preferably a group represented by the following general formula (1B-1), (1B-2), (1B-3), or (1D).

[0154] [ka]

[0155] (In the groups represented by the general formulae (1B-1), (1B-2), and (1B-3), n1 is 0, 1, 2, or 3; When n1 is 1, 2, or 3, L1 is an unsubstituted arylene group having 6 to 50 ring carbon atoms; an arylene group having 10 to 50 ring carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, when unsubstituted, the arylene group having 6 to 50 ring carbon atoms is not a fused ring, but is When two or more L1s are present, the two or more L1s are the same or different from each other, In the general formula (1B-1), R 51 ~R 54 , R 57 , and R 61 ~R 64 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 51 ~R 54 , R 57 , and R 61 ~R 64 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, * indicates the bonding position to the benz[a]anthracene ring in the general formula (1A), In the general formula (1B-2), R 51 ~R 53 , R 56 , R 57 , and R 71 ~R 74 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 51 ~R 53 , R 56 , R 57 , and R 71 ~R 74 are each independently R in the general formula (1B-1). 51 ~R 54 , R 57 , and R 61 ~R 64 is synonymous with * indicates the bonding position to the benz[a]anthracene ring in the general formula (1A), In the general formula (1B-3), R 51 ~R 55 , and R 81 ~R 84 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 51 ~R 55 , and R 81 ~R 84 are each independently R in the general formula (1B-1). 51 ~R 54 , R 57 , and R 61 ~R 64 is synonymous with * indicates the bonding position to the benz[a]anthracene ring in the general formula (1A), In the general formula (1D), R 21 ~R 30 one of which indicates a bonding position to the benz[a]anthracene ring in the general formula (1A), and R in the general formula (1D) which is not the bonding position 21 ~R 30 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (1D) which is not at a bonding position with the benz[a]anthracene ring in the general formula (1A), does not form the substituted or unsubstituted monocyclic ring, and does not form the substituted or unsubstituted fused ring 21 ~R 30 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, In the groups represented by the general formulae (1B-1), (1B-2), (1B-3), and (1D), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , and R 907 are each independently, 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 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.)

[0156] In the compound according to this embodiment, Ar1 may be a substituted or unsubstituted benzanthracenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted benzonaphthofuranyl group.

[0157] In the compound according to this embodiment, Ar1 does not necessarily include benzofluorene, benzoxanthene, and dibenzoxanthene.

[0158] In the compound according to this embodiment, R to R 12 and Ar1 preferably have at least one deuterium atom.

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

[0160] In the compound according to this embodiment, R5, R6, R7, R8, R 11 , or R 12 is also preferably a group represented by the general formula (1B). In the compound according to this embodiment, R6, R7, R 11 , or R 12 is also preferably a group represented by the general formula (1B). In the compound according to this embodiment, R 11 is also preferably a group represented by the general formula (1B). R5, R6, R7, R8, and R9 are the positions with higher electron density in the HOMO and LUMO or the positions where the singlet energy S1 is smaller. 11 , or R 12 When is a group represented by the general formula (1B), the excitation resistance of the compound according to this embodiment is likely to be improved, and the effect of extending the life of the organic EL device is likely to be obtained.

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

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

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

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

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

[0244] [ka]

[0245] [ka]

[0246] The compound according to this embodiment includes a benz[a]anthracene ring, a linker (L or L 101 ), and Ar1 or Ar 101 Since a deuterium atom is bonded to at least one of the above, the compound according to this embodiment is highly effective in stabilizing carrier resistance or excited states, and therefore, the compound according to this embodiment is expected to extend the life of organic EL devices. In particular, the benz[a]anthracene ring and Ar1 or Ar2, which have low singlet energy S1 and triplet energy T1 at the center of the excited state, 101 By bonding deuterium atoms to the electrons, it is expected that the electrons will have a longer lifespan.

[0247] Second Embodiment (organic electroluminescence element) The organic EL element according to this embodiment will be described. The organic EL device according to this embodiment contains the compound according to the first embodiment. The organic EL device according to this embodiment includes an anode, a cathode, and an organic layer disposed between the anode and the 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 organic compounds stacked together. The organic layer may further include an inorganic compound.

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

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

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

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

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

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

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

[0255] The method for measuring the maximum peak wavelength of a compound in this specification is as follows. -6 mol / L or more 10 -5 A toluene solution of 1000 mol / L or less is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measurement device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is maximum is defined as the maximum emission peak wavelength. In this specification, the maximum peak wavelength may also be referred to as the maximum fluorescence emission peak wavelength (FL-peak).

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

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

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

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

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

[0261] (luminescent compounds) In the organic EL device 1A, the light-emitting layer 5 preferably further contains a light-emitting compound (preferably a fluorescent compound).

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

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

[0264] [ka]

[0265] (In the general formula (3), R 301 ~R 310 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 301 ~R 310 At least one of the groups is a monovalent group represented by the following general formula (31): R which does not form the monocyclic ring, does not form the fused ring, and is not a monovalent group represented by the following general formula (31): 301 ~R 310 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.

[0266] [ka]

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

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

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

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

[0271] [ka]

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

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

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

[0275] [ka]

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

[0277] [ka]

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

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

[0280] [ka]

[0281] (In the general formula (36), X3 represents an oxygen atom or a sulfur atom; R 321 ~R 327 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 321 ~R 327 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, *L 302, L 303 , L 312 , L 313 , L 315 or L 316 )

[0282] X3 is preferably an oxygen atom.

[0283] R 321 ~R 327 At least one of the a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0284] In the general formula (31), Ar 301 is a group represented by the general formula (36), and Ar 302 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. In the general formulas (33) to (35), Ar 312 is a group represented by the general formula (36), and Ar 313 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. In the general formulas (33) to (35), Ar 315 is a group represented by the general formula (36), and Ar 316 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

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

[0286] [ka]

[0287] (In the general formula (37), R 311 ~R 318 are each independently R in the general formula (3) that is not a monovalent group represented by the general formula (31). 301 ~R 310 is synonymous with R 321 ~R 327 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 341 ~R 347 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 321 ~R 327 and R 341 ~R 347 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(R906 )(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 331 ~R 335 and R 351 ~R 355 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 groups, nitro groups, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

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

[0289] [ka]

[0290] [ka]

[0291] [ka]

[0292] [ka]

[0293] [ka]

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

[0295] [ka]

[0296] (In the general formula (4), Each Z is independently CRa or a nitrogen atom; Ring A1 and ring A2 each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, When there are a plurality of Ra, one or more pairs of adjacent two or more of the plurality of Ra are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, n21 and n22 each independently represent 0, 1, 2, 3, or 4; When a plurality of Rb's are present, one or more pairs of adjacent two or more Rb's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, When there are a plurality of Rc's, one or more pairs of adjacent two or more Rc's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ra, Rb, and Rc that do not form a single ring and do not form a fused ring each independently represent: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a 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.

[0297] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring A1 and ring A2 contains, as ring-forming atoms, two carbon atoms on the central fused two-ring structure of general formula (4). Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1.

[0298] The "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "heterocyclic group." The "heterocycle" of ring A1 and ring A2 contains the two carbon atoms on the central fused two-ring structure of general formula (4) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.

[0299] Rb is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A1, or any of the atoms forming the heterocycle as ring A1.

[0300] Rc is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as ring A2, or any of the atoms forming the heterocycle as ring A2.

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

[0302] [ka]

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

[0304] [ka]

[0305] (In the general formula (4b), L 402 and L 403 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, Ar 402 and Ar 403 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, Ar does not form the single ring and does not form the fused ring 402 and Ar 403 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

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

[0307] [ka]

[0308] (In the general formula (42), R 401 ~R 411 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 401 ~R 411 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.

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

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

[0311] [ka]

[0312] (In the general formula (4-1), two * are each independently bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle as the A1 ring in the general formula (4), or to a ring-forming atom of R in the general formula (42). 404 ~R 407 and combine with either The three * in the general formula (4-2) each independently bond to a ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocycle as the A1 ring in the general formula (4), or bond to R in the general formula (42). 404 ~R 407 and combine with either R 421 ~R 427 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 431 ~R 438 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 421 ~R 427and R 431 ~R 438 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.

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

[0314] [ka]

[0315] [ka]

[0316] [ka]

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

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

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

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

[0321] [ka]

[0322] [ka]

[0323] [ka]

[0324] [ka]

[0325] [ka]

[0326] (In the general formula (461), the general formula (462), the general formula (463), the general formula (464), the general formula (465), the general formula (466) and the general formula (467), R 421 ~R 427 are each independently R in the general formula (4-1). 421 ~R 427 is synonymous with R 431 ~R 438 are each independently R in the general formula (4-2). 431 ~R 438 is synonymous with R 440 ~R 448 and R 451 ~R 454 are each independently R in the general formula (42). 401 ~R 411 is synonymous with X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ) and R 801 , R 802 and R 803 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, Preferably, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, R 803 If there are multiple R 803 are either identical or different.)

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

[0328] (Compound represented by general formula (45)) The compound represented by general formula (45) will be explained.

[0329] [ka]

[0330] (In the general formula (45), R 461 and R 462 A set consisting of 462 and R 463 A set consisting of 464 and R 465 A set consisting of 465 and R 466 A set consisting of 466 and R 467 A set consisting of 468 and R 469 A set consisting of469 and R 470 and R 470 and R 471 two or more of the pairs selected from the group consisting of pairs of however, R 461 and R 462 and R 462 and R 463 A set consisting of and; R 464 and R 465 and R 465 and R 466 A set consisting of and; R 465 and R 466 and R 466 and R 467 A set consisting of and; R 468 and R 469 and R 469 and R 470 and R 469 and R 470 and R 470 and R 471 and do not simultaneously form a ring, R 461 ~R 471 The two or more rings formed by are the same or different, R does not form the monocyclic ring and does not form the fused ring 461 ~R 471 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.

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

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

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

[0334] [ka]

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

[0336] [ka]

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

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

[0339] (i) In the general formula (45), R n and R n+1 a substituent when the ring structure formed by the formula (I) has a substituent, (ii) In the general formula (45), R 461 ~R 471 , and (iii) R in equations (451) to (460) 4501 ~R 4514 , R 4515 ~R4525 are preferably each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or It is any one of groups selected from the group consisting of groups represented by the following general formulae (461) to (464).

[0340] [ka]

[0341] (In the general formulas (461) to (464), R d 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, X 46 is C(R 801 )(R 802 ), NR 803 , an oxygen atom or a sulfur atom, R 801 , R 802 and R 803 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, Preferably, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, R 803 If there are multiple R 803 are the same or different from each other, p1 is 5, p2 is 4, p3 is 3, p4 is 7, In the general formulae (461) to (464), * each independently indicates the bonding position to the ring structure. In the luminescent compound, R 901 ~R 907 is as defined above.

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

[0343] [ka]

[0344] [ka]

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

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

[0347] [ka]

[0348] [ka]

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

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

[0351] [ka]

[0352] [ka]

[0353] [ka]

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

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

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

[0357] [ka]

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

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

[0360] [ka]

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

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

[0363] [ka]

[0364] [ka]

[0365] [ka]

[0366] [ka]

[0367] [ka]

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371] [ka]

[0372] [ka]

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

[0374] [ka]

[0375] (In the general formula (5), R 501 ~R 507 and R 511 ~R 517 At least one pair of two or more adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 501 ~R 507 and R 511 ~R 517 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-(R905 ) 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. R 521 and R 522 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.

[0376] "R 501 ~R 507 and R 511 ~R 517 "A set of two or more adjacent pairs of R" is, for example, 501 and R 502 A set consisting of R 502 and R 503 A set consisting of R 503 and R504 A set consisting of R 505 and R 506 A set consisting of R 506 and R 507 A set consisting of R 501 and R 502 and R 503 It is a combination of a set consisting of:

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

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

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

[0380] [ka]

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

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

[0383] [ka]

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

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

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

[0387] In one embodiment, the substituent in the case of “substituted or unsubstituted” in the general formula (5), the general formula (52), and the general formula (53) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

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

[0389] [ka]

[0390] [ka]

[0391] [ka]

[0392] [ka]

[0393] [ka]

[0394]

change

[0395]

change

[0396]

change

[0397]

change

[0398]

change

[0399]

change

[0400]

change

[0401]

change

[0402]

change

[0403]

change

[0404]

change

[0405] [ka]

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

[0407] [ka]

[0408] (In the general formula (6), 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, R 601 and R 602 each independently bond to the ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601 and R 602 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0409] The rings a, b, and c are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, or substituted or unsubstituted heterocyclic rings having 5 to 50 ring atoms) fused to the central fused bicyclic structure of the general formula (6) composed of a boron atom and two nitrogen atoms.

[0410] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "aryl group." The "aromatic hydrocarbon ring" of ring a contains the three carbon atoms on the central fused two-ring structure of the general formula (6) as ring-forming atoms. The "aromatic hydrocarbon ring" of ring b and ring c contains the two carbon atoms on the central fused two-ring structure of general formula (6) as ring-forming atoms.

[0411] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom has been introduced into the "aryl group" described in specific example group G1. The "heterocycles" of ring a, ring b, and ring c have the same structure as the compounds in which a hydrogen atom has been introduced into the above-mentioned "heterocyclic group." The "heterocycle" of ring a contains three carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. The "heterocycle" of rings b and c contains two carbon atoms on the central fused bicyclic structure of general formula (6) as ring-forming atoms. Specific examples of "substituted or unsubstituted heterocycles having 5 to 50 ring atoms" include compounds in which a hydrogen atom has been introduced into the "heterocyclic group" described in specific example group G2.

[0412] R 601 and R 602 may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring contains the nitrogen atom on the central fused bicyclic structure of the general formula (6). In this case, the heterocyclic ring may contain a heteroatom other than the nitrogen atom. R 601 and R 602 is bonded to ring a, ring b, or ring c specifically means that an atom constituting ring a, ring b, or ring c is bonded to R 601 and R 602It means that the atoms that make up R are bonded together. 601 is bonded to the a ring, and R 601 and ring a may be fused to form a two-ring (or three- or more-ring) fused nitrogen-containing heterocycle. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. R 601 When is bonded to ring b, R 602 When R is bonded to ring a, 602 The same applies when is bonded to ring c.

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

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

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

[0416] [ka]

[0417] (In the general formula (62), R 601A is R 611 and R 621to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R 602A is R 613 and R 614 to form a substituted or unsubstituted heterocycle, or not to form a substituted or unsubstituted heterocycle, R that does not form the substituted or unsubstituted heterocycle 601A and R 602A 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 611 ~R 621 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, the monocyclic ring, or the fused ring. 611 ~R 621 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 )(R903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by 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.

[0418] R in the general formula (62) 601A and R 602A are R in the general formula (6), respectively. 601 and R 602 is a group corresponding to For example, R 601A and R 611 may be bonded to form a two-ring (or three- or more-ring) nitrogen-containing heterocyclic ring in which a ring containing the ring is fused with a benzene ring corresponding to ring a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing two- or more-ring fused heterocyclic groups in specific example group G2. 601A and R 621 If R 602A and R 613 When R is bonded, 602A and R 614 The same applies when the two are combined.

[0419] R 611 ~R 621 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or They may be bonded to each other to form a substituted or unsubstituted fused ring. For example, R 611 and R 612may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is fused to the six-membered ring to which they are bonded, and the fused ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0420] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0421] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0422] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, a hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0423] In one embodiment, R that does not contribute to ring formation 611 ~R 621 are each independently, a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 611 ~R 621 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

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

[0425] [ka]

[0426] (In the general formula (63), R 631 is R 646 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 633 is R 647 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 634 is R 651 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 641 is R 642 and either combine with each other to form a substituted or unsubstituted heterocycle, or do not form a substituted or unsubstituted heterocycle; R 631 ~R 651 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, the monocyclic ring, or the fused ring. 631 ~R 651 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.

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

[0428] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0429] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0430] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, a hydrogen atom, or It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0431] In one embodiment, R that does not contribute to ring formation 631 ~R 651 are each independently, a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 631 ~R 651 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

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

[0433] [ka]

[0434] (In the general formula (63A), R 661 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 662 ~R 665 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0435] In one embodiment, R 661 ~R 665 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

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

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

[0438] [ka]

[0439] (In the general formula (63B), R 671 and R 672 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 673 ~R 675 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ) a group represented by It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

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

[0441] [ka]

[0442] (In the general formula (63B'), R 672 ~R 675 are each independently R in the general formula (63B). 672 ~R 675 is equivalent to

[0443] In one embodiment, R 671 ~R 675 At least one of the a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -N(R 906 )(R 907 ) a group represented by It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0444] In one embodiment, R 672 teeth, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 671 and R 673 ~R 675 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 ) a group represented by It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

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

[0446] [ka]

[0447] (In the general formula (63C), R 681 and R 682 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. R 683 ~R 686 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

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

[0449] [ka]

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

[0451] In one embodiment, R 681 ~R 686 are each independently, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

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

[0453] The compound represented by the general formula (6) is first prepared by connecting the ring a, ring b, and ring c to a linking group (NR 601 and groups containing NR 602 The intermediate is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (reaction 2), and the final product is produced by linking the rings a, b, and c with a linking group (a group containing a boron atom) (reaction 2). In reaction 1, an amination reaction such as the Bachburt-Hartwig reaction can be applied. In reaction 2, a tandem hetero-Friedel-Crafts reaction can be applied.

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

[0455] [ka]

[0456] [ka]

[0457] [ka]

[0458] [ka]

[0459] [ka]

[0460] [ka]

[0461] [ka]

[0462]

change

[0463]

change

[0464]

change

[0465]

change

[0466]

change

[0467]

change

[0468]

change

[0469]

change

[0470]

change

[0471]

change

[0472] [ka]

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

[0474] [ka]

[0475] [ka]

[0476] (In the general formula (7), ring r is a ring represented by general formula (72) or general formula (73) fused at any position to an adjacent ring, ring q and ring s are each independently a ring represented by general formula (74) fused to an adjacent ring at any position, The p ring and the t ring each independently represent a structure represented by the general formula (75) or the general formula (76) fused at any position of the adjacent ring, X7 is an oxygen atom, a sulfur atom, or NR 702 is. R 701 If there are multiple R 701 teeth, joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 701 and R 702 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, Ar 701 and Ar 702 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, L 701 teeth, a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms; a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms; a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, m1 is 0, 1 or 2; m2 is 0, 1, 2, 3 or 4; m3 is independently 0, 1, 2 or 3; m4 is independently 0, 1, 2, 3, 4 or 5; R 701 If there are multiple R 701 are identical to or different from each other, When a plurality of X7s are present, the plurality of X7s are the same or different from one another, R 702 If there are multiple R 702 are identical to or different from each other, Ar 701 If there are multiple Ar 701 are identical to or different from each other, Ar 702 If there are multiple Ar 702 are identical to or different from each other, L 701 If there are multiple L 701 are either identical or different.)

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

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

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

[0480] [ka]

[0481] [ka]

[0482] [ka]

[0483] [ka]

[0484] [ka]

[0485] [ka]

[0486] (In the general formulae (71-1) to (71-6), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, and m3 are each R in the general formula (7). 701 , X7, Ar 701 , Ar 702 , L 701 , m1 and m3.)

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

[0488] [ka]

[0489] [ka]

[0490] [ka]

[0491] (In the general formulas (71-11) to (71-13), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, m3, and m4 are each R in the general formula (7). 701 , X7, Ar 701 , Ar 702 , L 701 , m1, m3 and m4.)

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

[0493] [ka]

[0494] [ka]

[0495] [ka]

[0496] [ka]

[0497] [ka]

[0498] (In the general formulas (71-21) to (71-25), R 701 , X7, Ar 701 , Ar 702 , L 701 , m1, and m4 are each R in the general formula (7). 701 , X7, Ar701 , Ar 702 , L 701 , m1 and m4.)

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

[0500] [ka]

[0501] [ka]

[0502] [ka]

[0503] (In the general formulas (71-31) to (71-33), R 701 , X7, Ar 701 , Ar 702 , L 701 , m2 to m4 are each R in the general formula (7). 701 , X7, Ar 701 , Ar 702 , L 701 , m2 to m4 are synonymous.)

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

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

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

[0507] [ka]

[0508] [ka]

[0509] [ka]

[0510] [ka]

[0511] [ka]

[0512] [ka]

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

[0514] [ka]

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

[0516] [ka]

[0517] (R not forming a divalent group represented by the general formula (82) 801 ~R 804 , and R 811 ~R 814 At least one of the above is a monovalent group represented by the following general formula (84): R that does not form a divalent group represented by the general formula (83) 805 ~R 808 , and R 821 ~R 824 At least one of the above is a monovalent group represented by the following general formula (84): X8 is an oxygen atom, a sulfur atom, or NR 809 and R which does not form a divalent group represented by the general formula (82) and the general formula (83) and is not a monovalent group represented by the general formula (84) 801 ~R 808 R is not a monovalent group represented by the general formula (84). 811 ~R 814 and R 821 ~R 824 , and R 809 are each independently, 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.

[0518] [ka]

[0519] (In the general formula (84), Ar 801 and Ar 802 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L 801 ~L 803 are each independently, single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms; a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, In the general formula (84), * indicates the bonding position with the ring structure represented by the general formula (8), the group represented by the general formula (82) or the general formula (83).

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

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

[0522] [ka]

[0523] [ka]

[0524] [ka]

[0525] (In the general formulae (81-1) to (81-6), X8 has the same meaning as X8 in general formula (8), R 801 ~R 824 at least two of the groups are monovalent groups represented by general formula (84), R which is not a monovalent group represented by the general formula (84) 801 ~R 824 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.

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

[0527] [ka]

[0528] [ka]

[0529] [ka]

[0530] [ka]

[0531] [ka]

[0532] [ka]

[0533] (In the general formulae (81-7) to (81-18), X8 has the same meaning as X8 in general formula (8), * is a single bond bonding to the monovalent group represented by the general formula (84), R 801 ~R 824 are each independently R which is not a monovalent group represented by the general formula (84) in the general formulas (81-1) to (81-6). 801 ~R 824 is equivalent to

[0534] R which does not form a divalent group represented by the general formula (82) and the general formula (83) and is not a monovalent group represented by the general formula (84) 801 ~R 808 and R which is not a monovalent group represented by the general formula (84). 811 ~R 814 and R 821 ~R 824 are preferably each independently 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, 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.

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

[0536] [ka]

[0537] (In the general formula (85), R 831 ~R840 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, * in the general formula (85) has the same meaning as * in the general formula (84).

[0538] [ka]

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

[0540] [ka]

[0541] (In the general formula (87), X 81 is an oxygen atom or a sulfur atom, R 841 ~R 848 One of the following is L 803 is a single bond that connects to R that is not a single bond 841 ~R 848 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.

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

[0543] [ka]

[0544] [ka]

[0545] [ka]

[0546] [ka]

[0547] [ka]

[0548] [ka]

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

[0550] [ka]

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

[0552] [ka]

[0553] (In the general formula (92), A 93 The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, X9 is NR 93 , C(R 94 )(R 95 ), Si(R 96 )(R 97 ), Ge(R 98 )(R 99 ), an oxygen atom, a sulfur atom, or a selenium atom; R 91 and R 92 teeth, joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the monocyclic ring and does not form the fused ring 91 and R 92 , and R 93 ~R 99 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.

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

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

[0556] [ka]

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

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

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

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

[0561] In one embodiment, ring A 93 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring. In one embodiment, X9 is an oxygen atom or a sulfur atom.

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

[0563] [ka]

[0564] [ka]

[0565] [ka]

[0566] [ka]

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

[0568] [ka]

[0569] [ka]

[0570] (In the general formula (10), ring Ax1 is a ring represented by general formula (10a) fused to an adjacent ring at any position, ring Ax2 is a ring represented by general formula (10b) fused to an adjacent ring at any position, In the general formula (10b), two * are bonded to any positions of the Ax3 ring, X A and X B are each independently C(R 1003 )(R 1004 ), Si(R 1005 )(R 1006 ), an oxygen atom or a sulfur atom; The Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms, Ar 1001 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 1001 ~R 1006 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, mx1 is 3 and mx2 is 2, Multiple R 1001 are identical to or different from each other, Multiple R 1002 are identical to or different from each other, ax is 0, 1 or 2; When ax is 0 or 1, the structures in the brackets shown as "3-ax" are the same or different from each other, If ax is 2, multiple Ar1001 are either identical or different.)

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

[0572] In one embodiment, ring Ax3 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

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

[0574] In one embodiment, ax is 1.

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

[0576] [ka]

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

[0578] [ka]

[0579] (In the general formula (63a), R 631 is R 646 may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. R 633 is R 647 may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. R 634 is R 651 may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. R 641 is R 642 may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring. R 631 ~R 651 One or more pairs of two or more adjacent joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted heterocyclic ring, the monocyclic ring, or the fused ring. 631 ~R 651 are each independently, hydrogen atoms, halogen atoms, cyano group, nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, provided that R does not form the substituted or unsubstituted heterocyclic ring, does not form the monocyclic ring, and does not form the fused ring. 631 ~R 651 At least one of the halogen atoms, cyano group, nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a 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.

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

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

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

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

[0584] [ka]

[0585] [ka]

[0586] [ka]

[0587] [ka]

[0588] [ka]

[0589] (In the general formulas (461) to (467), R 421 ~R 427 , R 431 ~R 436 , R 440 ~R 448 and R 451 ~R 454 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 437 , R 438 and R which does not form the monocyclic ring and does not form the fused ring. 421 ~R 427 , R 431 ~R 436 , R 440 ~R 448 and R 451 ~R 454 are each independently, 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, X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ) and R 801 , R 802 and R 803 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, Preferably, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are the same or different from each other, R 803 If there are multiple R 803 are either identical or different.)

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

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

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

[0593] [ka]

[0594] (In the general formula (41-3-1), R 423 , R 425 , R 426 , R 442 , R 444 and R 445 are each independently R in the general formula (41-3). 423 , R 425 , R 426 , R442 , R 444 and R 445 is equivalent to

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

[0596] [ka]

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

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

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

[0600] [ka]

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

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

[0603] [ka]

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

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

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

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

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

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

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

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

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

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

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

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

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

[0617] [ka]

[0618] (In the general formula (2), R 201 ~R 208 are each independently, 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 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 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 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, L 201 and L 202 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, Ar 201 and Ar 202 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0619] (In the second compound according to this embodiment, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 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 902If there are multiple R 902 are the same or different from each other, R 903 If there are multiple R 903 are the same or different from each other, R 904 If there are multiple R 904 are the same or different from each other, R 905 If there are multiple R 905 are the same or different from each other, R 906 If there are multiple R 906 are the same or different from each other, R 907 If there are multiple R 907 are the same or different from each other, R 801 If there are multiple R 801 are the same or different from each other, R 802 If there are multiple R 802 are either identical or different.)

[0620] In the organic EL element according to this embodiment, R 201 ~R 208 are each independently, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 801 a group represented by -COOR 802 a group represented by halogen atoms, a cyano group, or is a nitro group, L 201 and L 202 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, Ar 201 and Ar 202 are each independently, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

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

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

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

[0624] [ka]

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

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

[0635] [ka]

[0636] [ka]

[0637] [ka]

[0638] [ka]

[0639] [ka]

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[0641] [ka]

[0642] [ka]

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

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

[0646] [ka]

[0647] [ka]

[0648] [ka]

[0649] [ka]

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

[0656] In the second compound represented by the general formula (2), R 201 ~R 208 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, or -Si(R 901 )(R 902 )(R 903 ) is preferably a group represented by the formula (I).

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

[0658] In the organic EL element according to this embodiment, In the second compound represented by the general formula (2), R 201 ~R 208 are each independently, 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, or -Si(R 901 )(R 902 )(R 903 ) is preferably a group represented by the formula (I).

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

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

[0661] In the organic EL device according to this embodiment, for example, Ar 201 is a substituted or unsubstituted dibenzofuranyl group.

[0662] In the organic EL device according to this embodiment, for example, Ar 201 is an unsubstituted dibenzofuranyl group.

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

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

[0665] [ka]

[0666] In the organic EL device according to this embodiment, for example, Ar 201 represents a substituted or unsubstituted anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluoranthenyl group, a benzofluoranthenyl group, and At least one group selected from the group consisting of perylenyl groups.

[0667] In the organic EL device according to this embodiment, for example, Ar 201 is a substituted or unsubstituted fluorenyl group.

[0668] In the organic EL device according to this embodiment, for example, Ar 201 is a substituted or unsubstituted xanthenyl group.

[0669] In the organic EL device according to this embodiment, for example, Ar 201 is a benzoxanthenyl group.

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

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

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[0698] (First luminescent compound and second luminescent compound) In the organic EL element 1B, the first light-emitting layer 51 preferably further contains a first light-emitting compound (preferably a fluorescent compound). In the organic EL element 1B, the second light-emitting layer 52 preferably further contains a second light-emitting compound (preferably a fluorescent compound). When the first light-emitting layer 51 contains a first light-emitting compound and the second light-emitting layer 52 contains a second light-emitting compound, the first light-emitting compound and the second light-emitting compound may be the same as or different from each other. Examples of the first light-emitting compound and the second light-emitting compound include the same light-emitting compounds as those exemplified in the organic EL device 1A.

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

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

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

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

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

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

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

[0706] In the organic EL device 1B, it is preferable that the triplet energy T1(H1) of the first compound and the triplet energy T1(H2) of the second compound satisfy the relationship of the following mathematical formula (Mathematical Formula 1). T1(H1)>T1(H2) ... (Number 1)

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

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

[0709] In the organic EL device according to this embodiment, triplet excitons generated by recombination of holes and electrons in the first light-emitting layer are thought to be less likely to be quenched at the interface between the first light-emitting layer and the organic layer, even if excess carriers are present at the interface between the first light-emitting layer and the organic layer that is in direct contact with the first light-emitting layer. For example, when the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching by excess electrons is thought to occur. On the other hand, when the recombination region is locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching by excess holes is thought to occur. Organic EL device 1B includes at least two light-emitting layers (i.e., first light-emitting layer 51 and second light-emitting layer 52) that satisfy a predetermined relationship. First light-emitting layer 51 and second light-emitting layer 52 are provided such that triplet energy T1(H1) of the first compound in first light-emitting layer 51 and triplet energy T1(H2) of the second compound in second light-emitting layer 52 satisfy the relationship shown in the above mathematical formula (Mathematical Formula 1). This allows triplet excitons generated in first light-emitting layer 51 to migrate to second light-emitting layer 52 without being quenched by excess carriers, and prevents reverse migration from second light-emitting layer 52 to first light-emitting layer 51. As a result, the TTF mechanism is activated in second light-emitting layer 52, resulting in efficient generation of singlet excitons and improved luminous efficiency. In this way, the organic EL element 1B includes, as distinct regions, the first light-emitting layer 51 that mainly generates triplet excitons and the second light-emitting layer 52 that mainly exhibits the TTF mechanism by utilizing the triplet excitons transferred from the first light-emitting layer 51. The second compound in the second light-emitting layer 52 is a compound having a smaller triplet energy than the first compound in the first light-emitting layer, and this difference in triplet energy improves the luminous efficiency.

[0710] (Triplet energy T1) The triplet energy T1 can be measured by the following method. The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at 10 -5 mol / L or more 10 -4 A solution is prepared by dissolving the compound to a concentration of 0.1 mol / L or less, and this solution is placed in a quartz cell to be used as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), and a tangent line is drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis is determined. edge Based on [nm], the amount of energy calculated using the following conversion formula (F1) is taken as the triplet energy T1. Conversion formula (F1): T1[eV]=1239.85 / λ edge

[0711] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum 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 that is 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 defined as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using an F-4500 spectrofluorophotometer 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 cryogenic container, an excitation light source, and a light-receiving device.

[0712] In the organic EL element 1B, when the first light-emitting layer 51 contains a first compound and a first light-emitting compound, it is preferable that the singlet energy S1(H1) of the first compound and the singlet energy S1(D3) of the first light-emitting compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(H1)>S1(D3)…(Number 2)

[0713] (singlet energy S1) The following method can be mentioned as a method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method). 10 of the compounds to be measured -5 mol / L or more 10 -4A toluene solution of 1000 mol / L or less is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the singlet energy S1. 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.

[0714] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall 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 values ​​on the longest wavelength side.

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

[0716] In the organic EL element 1B, when the second light-emitting layer 52 contains a second compound and a second light-emitting compound, it is preferable that the singlet energy S1(H2) of the second compound and the singlet energy S1(D4) of the second light-emitting compound satisfy the relationship of the following mathematical formula (Mathematical Formula 3). S1(H2)>S1(D4)…(Number 3)

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

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

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

[0720] In this embodiment, the first light-emitting layer 51 may contain materials other than the first compound and the first light-emitting compound. The first light-emitting layer 51 may contain only one type of first compound, or may contain two or more types. The first light-emitting layer 51 may contain only one type of first light-emitting compound, or may contain two or more types.

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

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

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

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

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

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

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

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

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

[0730] When the intervening layer contains a plurality of intervening layer materials, the content of each intervening layer material is preferably 10% by mass or more of the total mass of the intervening layer. The intervening layer preferably contains the intervening layer material in an amount of 60% by mass or more of the total mass of the intervening layer, more preferably 70% by mass or more of the total mass of the intervening layer, even more preferably 80% by mass or more of the total mass of the intervening layer, even more preferably 90% by mass or more of the total mass of the intervening layer, and even more preferably 95% by mass or more of the total mass of the intervening layer. The intervening layer may contain only one type of intervening layer material, or may contain two or more types. When the intervening layer contains two or more types of intervening layer materials, the upper limit of the total content of the two or more intervening layer materials is 100% by mass. It should be noted that this embodiment does not exclude the case where the intervening layer contains a material other than the intervening layer material.

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

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

[0733] The structure of each layer common to the organic EL element 1A and the organic EL element 1B will be further described below. Hereinafter, the reference numerals may be omitted.

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

[0735] (anode) The anode 3 formed on the substrate is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or higher). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of metal materials (e.g., titanium nitride).

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

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

[0738] Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used. These include 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 metals (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these metals. Vacuum deposition and sputtering methods can be used to form the anode using alkali metals, alkaline earth metals, and alloys containing these metals. Furthermore, when using silver paste, coating methods and inkjet methods can be used.

[0739] (cathode) It is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less) for the cathode 4. Specific examples of such cathode materials include elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.

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

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

[0742] (hole injection layer) The hole injection layer 61 is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0743] In addition, 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 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). [N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, such as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), are also included.

[0744] Furthermore, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Acid-added polymeric compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

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

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

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

[0748] (electron transport layer) The electron transport layer 71 is a layer containing a substance with high electron transport properties. The electron transport layer 71 can be made of 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; or 3) polymer compounds. Specifically, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as 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-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 -6 cm 2 / (V·s) or more. Note that other substances may be used as the electron-transporting layer as long as they have a higher electron-transporting property than a hole-transporting property. The electron-transporting layer may be formed as a single layer or as a stack of two or more layers made of the above-mentioned substances.

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

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

[0751] Alternatively, the electron injection layer 72 may be made of a composite material obtained by mixing an organic compound and an electron donor (donor). Such composite materials have excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons. Specifically, for example, the 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, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxide, calcium oxide, and barium oxide. Furthermore, Lewis bases such as magnesium oxide can also be used. Furthermore, organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

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

[0753] (film thickness) The thickness of each organic layer in the organic EL device of this embodiment is not limited unless otherwise specified above. Generally, 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 in the organic EL device is usually preferably in the range of several nm to 1 μm.

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

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

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

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

[0758] Furthermore, 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 adjacent to the cathode side of the light-emitting layer, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) located closer to the cathode than 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. Furthermore, 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) located closer to the anode than 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 excitation energy from leaking from the light-emitting layer to surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the barrier layer (e.g., electron transport layer and hole transport layer). The light-emitting layer and the barrier layer are preferably in contact with each other.

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

[0760] 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. <Compound> The structure of the compound represented by general formula (100A) used in the production of the organic EL device according to the example is shown below.

[0761] [ka]

[0762] [ka]

[0763] [ka]

[0764] [ka]

[0765] [ka]

[0766] [ka]

[0767] [ka]

[0768] [ka]

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

[0770] [ka]

[0771] [ka]

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

[0773] [ka]

[0774] [ka]

[0775] [ka]

[0776] <Fabrication of Organic EL Devices (1)> An organic EL device was fabricated and evaluated as follows.

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

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

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

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

[0781] ·Life span (LT95) The resulting organic EL device was subjected to a current density of 50 mA / cm 2 A voltage was applied so that the voltage was such that the time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hours)) was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0782] [Table 1]

[0783] <Fabrication of Organic EL Devices (2)> An organic EL device was fabricated and evaluated as follows.

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

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

[0786] <Evaluation of Organic EL Devices (2)> The organic EL devices prepared in Examples 3, 4, 5, 6, 7, 8, 9, 10, 11, and 12 were evaluated as follows. The evaluation results are shown in Table 2.

[0787] ·Life span (LT95) The resulting organic EL device was subjected to a current density of 50 mA / cm 2 A voltage was applied so that the voltage was such that the time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hours)) was measured. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0788] [Table 2]

[0789] <Fabrication of Organic EL Devices (3)> An organic EL device was fabricated and evaluated as follows.

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

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

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

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

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

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

[0796] [Table 3]

[0797] <Fabrication of Organic EL Devices (4)> An organic EL device was fabricated and evaluated as follows.

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

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

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

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

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

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

[0804] [Table 4]

[0805] <Fabrication of Organic EL Devices (5)> An organic EL device was fabricated and evaluated as follows.

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

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

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

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

[0810] [Table 5]

[0811] <Fabrication of Organic EL Devices (6)> An organic EL device was fabricated and evaluated as follows.

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

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

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

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

[0816] [Table 6]

[0817] <Fabrication of Organic EL Devices (7)> An organic EL device was fabricated and evaluated as follows.

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

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

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

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

[0822] [Table 7]

[0823] <Compound evaluation> (Triplet energy T1) The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to prepare a solution, and this solution was placed in a quartz cell to serve as a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this measurement sample was measured at low temperature (77 [K]), and a tangent was drawn to the rising edge of the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge The amount of energy calculated from the following conversion formula (F1) based on [nm] was taken as the triplet energy T1. The results are shown in Tables 1 and 2. The triplet energy T1 may have an error of about 0.02 eV depending on the measurement conditions. Conversion formula (F1): T1[eV]=1239.85 / λ edge

[0824] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum 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 that is 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 defined 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 F-4500 spectrofluorometer.

[0825] (singlet energy S1) A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) was measured at room temperature (300 K). A tangent line was drawn to the trailing edge of the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis was substituted into the following conversion formula (F2) to calculate the singlet energy S1. The results are shown in Tables 1 and 2. Conversion formula (F2): S1[eV]=1239.85 / λedge The absorption spectrum measuring device used was a spectrophotometer manufactured by Hitachi (device name: U3310).

[0826] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward longer wavelengths, consider the tangent at each point on the curve. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the slope is minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is considered to be the tangent to the fall 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 values ​​on the longest wavelength side.

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

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

[0829] [ka]

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

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

[0832] [ka]

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

[0834] [ka]

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

[0836] [Synthesis Example 3: Synthesis of Compound BH1-3] Compounds BH1-3 were synthesized according to the following synthetic route.

[0837] [ka]

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

[0839] [ka]

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

[0841] [Synthesis Example 4: Synthesis of Compound BH1-4] Compounds BH1-4 were synthesized according to the following synthetic route.

[0842] [ka]

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

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

[0845] [ka]

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

[0847] [Synthesis Example 6: Synthesis of Compound BH1-6] Compounds BH1-6 were synthesized according to the following synthetic route.

[0848] [ka]

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

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

[0851] [ka]

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

[0853] [Synthesis Example 8: Synthesis of Compound BH1-8] Compounds BH1-8 were synthesized according to the following synthetic route.

[0854] [ka]

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

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

[0857] [ka]

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

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

[0860] [ka]

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

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

[0863] [ka]

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

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

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

[0867] [ka]

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

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

Claims

1. A compound represented by the following general formula (1A): 【Chemical 1】 (In the general formula (1A), R 5 , R 6 , R 7 , R 8 , R 11 , or R 12 is a group represented by the general formula (1B) above; R １ ~R4, R ９ , R 10 , and R 5 to R 6 other than the group represented by formula (1B) ８ , R 11 , and R １２ are each independently, 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 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 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ８０１ a group represented by -COOR ８０２ 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 ９０２ , R ９０３ , R ９０４ , R ９０５ , R ８０１ , and R ８０２ 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 R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, In the general formula (1B), n1 is 0 or 1, L when n1 is 1 １ represents an unsubstituted arylene group having 6 to 18 ring carbon atoms, provided that the unsubstituted arylene group having 6 to 18 ring carbon atoms represented by L 1 is not a fused ring, Ar １ represents an aryl group having four substituted or unsubstituted rings fused together, * indicates the bonding position to the benz[a]anthracene ring in general formula (1A), However, R in the general formula (1A) １ ~R １２ and L in the general formula (1B). １ and Ar １ At least one of the groups has at least one deuterium atom, and L １ When only L has a deuterium atom, １ Among the rings constituting the formula (1A), a deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in the formula (1A).

2. In the compound of claim 1, L １ is a divalent group derived from a phenyl group, a p-biphenyl group, an m-biphenyl group, or an o-biphenyl group by removing one hydrogen atom on the aryl ring; compound.

3. In the compound of claim 1, n1 is 1. compound.

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

5. In the compound of claim 1, At least R １ ~R １２ is a deuterium atom, compound.

6. In the compound of claim 1, R ６ , R ７ , R １１ , or R １２ is a group represented by general formula (1B), compound.

7. In the compound according to claim 6, R １１ is a group represented by general formula (1B), compound.

8. In the compound according to claim 7, R １ ~R １０ and R １２ are all deuterium atoms, compound.

9. In the compound of claim 1, The groups described as "substituted or unsubstituted" are all "unsubstituted" groups, The rings described as "substituted or unsubstituted" are all "unsubstituted" rings. compound.

10. Contains a compound according to any one of claims 1 to 9 Organic electroluminescent element.

11. The organic electroluminescence device according to claim 10, an anode; A cathode; an organic layer disposed between the anode and the cathode; At least one of the organic layers contains the compound. Organic electroluminescent element.

12. The organic electroluminescence device according to claim 11, the organic layer has a light-emitting region; the light-emitting region includes at least one light-emitting layer; the light-emitting layer contains the compound, Organic electroluminescent element.

13. an anode; A cathode; a light-emitting region disposed between the anode and the cathode; the light-emitting region includes a first light-emitting layer and a second light-emitting layer; The first light-emitting layer contains a first compound represented by the following general formula (100A): the second light-emitting layer contains a second compound, Organic electroluminescent element. 【Chemistry 2】 (In the general formula (100A), R 105 , R 106 , R 107 , R 108 , R 111 , or R 112 is a group represented by the general formula (100B) above; R 101 to R 104 , R 109 , R 110 , and R 105 to R 108 , R 111 , and R other than the group represented by formula (100B) １１２ are each independently, 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 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 a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ８０１ a group represented by -COOR ８０２ 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 ９０２ , R ９０３ , R ９０４ , R ９０５ , R ８０１ , and R ８０２ 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 R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ８０１ If there are multiple R ８０１ are the same or different from each other, R ８０２ If there are multiple R ８０２ are the same or different from each other, In the general formula (100B), n101 is 0 or 1, L when n101 is 1 １０１ represents an unsubstituted arylene group having 6 to 18 ring carbon atoms, provided that the unsubstituted arylene group having 6 to 18 ring carbon atoms represented by L 101 is not a fused ring, Ar １０１ represents an aryl group having four substituted or unsubstituted rings fused together, * indicates the bonding position to the benz[a]anthracene ring in general formula (100A), However, R in the general formula (100A) １０１ ~R １１２ and L in the general formula (100B). １０１ and Ar １０１ At least one of the groups has at least one deuterium atom, and L １０１ When only L has a deuterium atom, １０１ A deuterium atom is bonded to the ring that is directly bonded to the benz[a]anthracene ring in general formula (100A) among the rings that constitute the formula (100A).

14. The organic electroluminescence device according to claim 13, The triplet energy T of the first compound １ (H1) and the triplet energy T of the second compound １ (H2) satisfies the relationship of the following formula (Formula 1): Organic electroluminescent element. T １ (H1)>T １ (H2) …(Number 1)

15. The organic electroluminescence device according to claim 13, L １０１ is a divalent group derived from a phenyl group, a p-biphenyl group, an m-biphenyl group, or an o-biphenyl group by removing one hydrogen atom on the aryl ring; Organic electroluminescent element.

16. 14. The organic electroluminescence device according to claim 13, wherein n101 is 1. Organic electroluminescent element.

17. 14. The organic electroluminescence device according to claim 13, wherein n101 is 0. Organic electroluminescent element.

18. The organic electroluminescence device according to claim 13, At least R １０１ ~R １１２ is a deuterium atom, Organic electroluminescent element.

19. The organic electroluminescence device according to claim 13, R １０６ , R １０７ , R １１１ , or R １１２ is a group represented by general formula (100B). Organic electroluminescent element.

20. 20. The organic electroluminescence device according to claim 19, R １１１ is a group represented by general formula (100B). Organic electroluminescent element.

21. The organic electroluminescence device according to claim 20, R １０１ ~R １１０ and R １１２ are all deuterium atoms, Organic electroluminescent element.

22. The organic electroluminescence device according to claim 13, The groups described as "substituted or unsubstituted" are all "unsubstituted" groups, The rings described as "substituted or unsubstituted" are all "unsubstituted" rings. Organic electroluminescent element.

23. The organic electroluminescence device according to claim 13, the first light-emitting layer and the second light-emitting layer are in direct contact with each other; Organic electroluminescent element.

24. The organic electroluminescence device according to claim 13, the first light-emitting layer is disposed between the anode and the second light-emitting layer; Organic electroluminescent element.

25. The organic electroluminescence device according to claim 13, the first light-emitting layer contains a first light-emitting compound, and the second light-emitting layer contains a second light-emitting compound; the first luminescent compound and the second luminescent compound are each independently a compound that emits light having a maximum peak wavelength of 500 nm or less; Organic electroluminescent element.

26. The organic electroluminescence device according to claim 13, a hole transport layer between the anode and the light-emitting region; Organic electroluminescent element.

27. The organic electroluminescence device according to claim 13, an electron transport layer between the cathode and the light-emitting region; Organic electroluminescent element.

28. An electronic device equipped with the organic electroluminescence element according to any one of claims 13 to 27.

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