Compound, organic electroluminescence element, and electronic device

Abstract

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

Description

Technical Field

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

Background Art

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

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0004] One object of the present invention is to provide a compound capable of improving the lifespan of an organic electroluminescence device, an organic electroluminescence device containing the compound, and an electronic device equipped with the organic electroluminescence device. Another object of the present invention is to provide an organic electroluminescence device with an improved lifespan and an electronic device equipped with the organic electroluminescence device.

Means for Solving the Problems

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

Chemical formula

[0006] (In the general formula (1A), R4 to R8 and R 10 ~R 12 One of them is a group represented by the general formula (1B), R1 to R3, R9, and R4 to R8 and R 10 ~R 12 other than the group represented by the general formula (1B) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 group represented by, -COOR 802 group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 , R 902 , R 903 , R 904 , R 905 , R 801 , and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When a plurality of R 901 exist, the plurality of R are the same as or different from each other, 902 When a plurality of R 902 exist, the plurality of R are the same as or different from each other, 903 When a plurality of R 903 exist, the plurality of R are the same as or different from each other, 904 When a plurality of R 904 exist, the plurality of R are the same as or different from each other, 905 When a plurality of R 905 exist, the plurality of R are the same as or different from each other, 801 When a plurality of R 801 exist, the plurality of R are the same as or different from each other, 802 When a plurality of R 802 exist, the plurality of R In the general formula (1B), n1 is 0 or an integer of 1 or more, When n1 is an integer of 1 or more, L1 is An arylene group having 6 to 50 ring-forming carbon atoms without substitution, An arylene group having 10 to 50 ring-forming carbon atoms, in which two or more rings, which may be substituted or unsubstituted, are fused, or A divalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, provided that the arylene group having 6 to 50 ring-forming carbon atoms in the case of no substitution is not a condensed ring, when two or more L1 are present, the two or more L1 are the same as or different from each other, Ar1 is An aryl group in which four or more rings, which may be substituted or unsubstituted, are fused, or A heterocyclic group in which four or more rings, which may be substituted or unsubstituted, are fused, * indicates the bonding position with the benz[a]anthracene ring in the general formula (1A), provided that at least one of R1 to R 12 , and at least one of L1 and Ar1 in the general formula (1B) has at least one deuterium atom. When only L1 has a deuterium atom, the deuterium atom is bonded to the ring 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 a 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 having an anode, a cathode, and a light-emitting region disposed between the anode and the cathode, wherein 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), and the second light-emitting layer contains a second compound. 。

[0009]

Chemical formula

[0010] (In the general formula (100A), R 101 ~R 112 One of them is a group represented by the general formula (100B), Rs other than the group represented by the general formula (100B) 101 ~R 112 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 )-represented group, -COOR 802 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 、R 902 、R 903 、R 904 、R 905 、R 801 、and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring-forming carbon atoms which may be substituted or unsubstituted, an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted, or a heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted, R 901 when a plurality of R's exist, the plurality of R's 901 are the same as or different from each other, R 902 when a plurality of R's exist, the plurality of R's 902 are the same as or different from each other, R 903 when a plurality of R's exist, the plurality of R's 903 are the same as or different from each other, R 904 when a plurality of R's exist, the plurality of R's 904 are the same as or different from each other, R 905 when a plurality of R's exist, the plurality of R's 905 are the same as or different from each other, R 801 when a plurality of R's exist, the plurality of R's 801 are the same as or different from each other, R 802 when a plurality of R's exist, the plurality of R's 802 are the same as or different from each other, In the general formula (100B), n101 is 0 or an integer of 1 or more, when n101 is an integer of 1 or more, L 101 is an unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, an arylene group having 10 to 50 ring-forming carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a divalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted, provided that the arylene group having 6 to 50 ring-forming carbon atoms in the unsubstituted case is not a condensed ring, L 101 when two or more L's exist, the two or more L's 101 are the same as or different from each other, Ar101 is an aryl group in which 3 or more rings of substituted or unsubstituted rings are fused, or a heterocyclic group in which 3 or more rings of substituted or unsubstituted rings are fused, * indicates the bonding position with the benz[a]anthracene ring in the general formula (100A), provided that R 101 ~R 112 , and L 101 and Ar 101 in the general formula (100B), at least one of them has at least one deuterium atom. When only L 101 has a deuterium atom, 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 L 101 .)

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

[0012] According to one aspect of the present invention, a compound capable of improving the lifetime of an organic electroluminescence element, an organic electroluminescence element containing the compound, and an electronic device equipped with the organic electroluminescence element can be provided. Further, according to one aspect 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 Description of the Drawings

[0013]

Figure 1

Figure 2

Mode for Carrying Out the Invention

[0014] [Definition] As used herein, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0015] As used herein, in a chemical structural formula, at a bondable position where symbols such as "R" or "D" representing a deuterium atom are not explicitly shown, it is assumed that a hydrogen atom, namely, a protium atom, a deuterium atom, or a tritium atom is bonded.

[0016] As used herein, the number of ring-forming carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a condensed-ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same shall apply to the "number of ring-forming carbon atoms" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the number of ring-forming carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring-forming carbon atoms of a 9,9'-spirobifluorenyl group is 25. Also, when, for example, an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms of a benzene ring substituted with an alkyl group is 6. Also, when, for example, an alkyl group is substituted as a substituent on a naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms of a naphthalene ring substituted with an alkyl group is 10.

[0017] As used herein, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic, condensed ring, and ring assembly) (e.g., monocyclic compound, condensed ring compound, bridged compound, carbocyclic compound, and heterocyclic compound). Atoms that do not constitute the ring (e.g., hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. Unless otherwise specified, the "number of ring-forming atoms" described below shall be the same. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Also, for example, the number of hydrogen atoms bonded to a carbon atom of a quinazoline ring or the number of atoms constituting a substituent is not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0018] As used herein, in the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms", "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents when the ZZ group is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0019] As used herein, in the expression "substituted or unsubstituted ZZ group having XX to YY atoms", "XX to YY atoms" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is greater 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 means the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in an "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. Also, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0021] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.

[0022] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of an "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18. Unless otherwise specified in this specification, the number of ring-forming atoms of an "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkyl group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. The number of ring-forming carbon atoms of the "unsubstituted cycloalkyl group" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification. The number of ring-forming carbon atoms of the "unsubstituted arylene group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification. The number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification. The number of carbon atoms of the "unsubstituted alkylene group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6, 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 groups (specific example group G1A) and substituted aryl groups (specific example group G1B), etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "substituted aryl group".) In this specification, when simply referring to the "aryl group", it includes both the "unsubstituted aryl group" and the "substituted aryl group". The "substituted aryl group" means a group in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced by substituents. Examples of the "substituted aryl group" include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" in the following specific example group G1A are replaced by substituents, and examples of the substituted aryl groups in the following specific example group G1B. It should be noted that the examples of the "unsubstituted aryl group" and the "substituted aryl group" listed here are only examples, and the "substituted aryl group" described in this specification includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent.

[0024] ·Aryl group without substitution (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, Benzoanthryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzochrysenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetracenyl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perylenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0025]

Chemical formula

[0026]

Chem.

[0027] ·Aryl group for substitution (specific example group G1B): o-Tolyl group, m-Tolyl group, p-Tolyl group, Para-Xylyl group, Meta-Xylyl group, Ortho-Xylyl group, Para-Isopropylphenyl group, Meta-Isopropylphenyl group, Ortho-Isopropylphenyl group, Para-t-Butylphenyl group, Meta-t-Butylphenyl group, Ortho-t-Butylphenyl group, 3,4,5-Trimethylphenyl group, 9,9-Dimethylfluorenyl group, 9,9-Diphenylfluorenyl group, 9,9-Bis(4-methylphenyl)fluorenyl group, 9,9-Bis(4-isopropylphenyl)fluorenyl group, 9,9-Bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from the ring structures represented by the general formulas (TEMP-1) to (TEMP-15) are replaced by substituents.

[0028] ·"Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described in this specification is a monocyclic group or a condensed ring group. The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group"). In this specification, when simply referring to the "heterocyclic group", it includes both the "unsubstituted heterocyclic group" and the "substituted heterocyclic group". The "substituted heterocyclic group" means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups in the following specific example group G2B, etc. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification also includes groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" of specific example group G2B are further replaced by substituents.

[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 the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

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

[0031] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, Isooxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl group, Isoindolyl group, Indolizinyl group, Quinolizinyl group, Quinolyl group, Isoquinolyl group, Cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenanthridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, and a diazacarbazolyl group.

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

[0033] · an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazaazadibenzothiophenyl group (diazaazadibenzothienyl group), Azananofluorophenyl group (azananofluorothienyl group), and Diazaazananofluorophenyl group (diazaazananofluorothienyl group).

[0034] ·A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0035]

Chemical formula

[0036]

Chemical formula

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

[0038] ·A substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-Phenyl)carbazolyl group, (9-Biphenylyl)carbazolyl group, (9-Phenyl)phenylcarbazolyl group, (9-Naphthyl)carbazolyl group, Diphenylcarbazol-9-yl group, Phenylcarbazol-9-yl group, Methylbenzimidazolyl group, Ethylbenzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group, and biphenylylquinazolinyl group.

[0039] ·Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and Monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene].

[0040] ·Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and Monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].

[0041] ·A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by the general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4):

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

[0043] · "Substituted or unsubstituted alkyl group" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (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 referred to as "alkyl group", both "unsubstituted alkyl group" and "substituted alkyl group" are included. "Substituted alkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced by substituents. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl groups" (specific example group G3A) are replaced by substituents, and examples of the substituted alkyl groups (specific example group G3B), etc. In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of specific example group G3B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "substituted alkyl group" of specific example group G3B is further replaced by a substituent.

[0044] · Unsubstituted alkyl group (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 group (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 in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B). (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when simply referring to an "alkenyl group", it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group". The "substituted alkenyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced by substituents. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl groups" (specific example group G4A) have substituents, and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of the "unsubstituted alkenyl group" and the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in this specification includes groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents.

[0047] · Unsubstituted alkenyl group (specific example group G4A): Vinyl group, Allyl group, 1-Butenyl group, 2-Butenyl group, and 3-Butenyl group.

[0048] ·Alkenyl groups for substitution (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), etc. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group"). Hereinafter, when simply referring to an "alkynyl group", it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group". The "substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are replaced by substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (specific example group G5A) are replaced by substituents, etc.

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

[0051] ·"Substituted or unsubstituted cycloalkyl group" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B), etc. (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 simply referring to the "cycloalkyl group", it includes both the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group". The "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl groups" (specific example group G6A) are replaced by substituents, and examples of the substituted cycloalkyl groups (specific example group G6B), etc. It should be noted that the examples of the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group" listed here are only examples, and the "substituted cycloalkyl group" described in this specification includes groups in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of specific example group G6B are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl group" of specific example group G6B are further replaced by substituents.

[0052] · Unsubstituted cycloalkyl groups (specific example group G6A): 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] · "A group represented by -Si(R 901 )(R 902 )(R 903 )" Examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Herein, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The plurality of G1 in -Si(G1)(G1)(G1) are the same as or different from each other. The plurality of G2 in -Si(G1)(G2)(G2) are the same as or different from each other. The plurality of G1 in -Si(G1)(G1)(G2) are the same as or different from each other. The plurality of G2 in -Si(G2)(G2)(G2) are the same as or different from each other. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The plurality of G6 in -Si(G6)(G6)(G6) are the same as or different from each other.

[0055] · "A group represented by -O-(R 904 )" Examples of the group represented by -O-(R904 ) Examples of the group represented by (specific example group G8) include -O(G1), -O(G2), -O(G3), and -O(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0056] · "Group represented by -S-(R 905 )" Examples of the group represented by -S-(R 905 ) described in this specification (specific example group G9) include -S(G1), -S(G2), -S(G3), and -S(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0057] · "Group represented by -N(R 906 )(R 907 )" Examples of the group represented by -N(R 906 )(R 907 ) described in this specification (specific example group G10) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2. G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6. The plurality of G1 in -N(G1)(G1) are the same as or different from each other. The plurality of G2 in -N(G2)(G2) are the same as or different from each other. The plurality of G3 in -N(G3)(G3) are the same as or different from each other. The plurality of G6 in -N(G6)(G6) are the same as or different from each other.

[0058] · "halogen atom" Specific examples (Specific Example Group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0059] · "substituted or unsubstituted fluoroalkyl group" As used herein, the term "substituted or unsubstituted fluoroalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced by substituents. It should be noted that the "substituted fluoroalkyl group" described herein includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted fluoroalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by fluorine atoms, and the like.

[0060] · "substituted or unsubstituted haloalkyl group" As used herein, the term "substituted or unsubstituted haloalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by halogen atoms. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted haloalkyl group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced by substituents. It should be noted that the "substituted haloalkyl group" described herein also includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted haloalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by halogen atoms. The haloalkyl group may be referred to as a halogenated alkyl group.

[0061] · "Substituted or unsubstituted alkoxy group" Specific examples of the "substituted or unsubstituted alkoxy group" described herein are groups represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkoxy group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18.

[0062] · "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" described herein are groups represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkylthio group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18.

[0063] · "Substituted or unsubstituted aryloxy group" Specific examples of the "substituted or unsubstituted aryloxy group" described in this specification are groups represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring-forming 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" Specific examples of the "substituted or unsubstituted arylthio group" described in this specification are groups represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring-forming 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" Specific examples of the "trialkylsilyl group" described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms of each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in this specification.

[0066] · "Substituted or unsubstituted aralkyl group" Specific examples of the "substituted or unsubstituted aralkyl group" described in this specification include a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, the "aralkyl group" is a group in which a hydrogen atom of the "alkyl group" is replaced by an "aryl group" as a substituent, and is one aspect of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted by an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group, etc.

[0067] The substituted or unsubstituted aryl group described in this specification is preferably a 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, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group, etc., unless otherwise specified in this specification.

[0068] The substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyl dibenzothiophenyl group, etc., unless otherwise described in this specification.

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

[0070]

Chem.

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

[0072]

Chem.

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

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

[0075]

Chemical formula

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

[0077] Unless otherwise specified herein, the substituted or unsubstituted alkyl group described in this specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, etc.

[0078] · "Substituted or unsubstituted arylene group" Unless otherwise specified herein, 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 "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1, etc.

[0079] · "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified herein, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the above "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 heterocyclic ring from the "substituted or unsubstituted heterocyclic group" described in specific example group G2, etc.

[0080] · "Substituted or unsubstituted alkylene group" The "substituted or unsubstituted alkylene group" described in this specification is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3 and the like.

[0081] The substituted or unsubstituted arylene group described in this specification is, unless otherwise specified in this specification, preferably a group of any one of the following general formulas (TEMP-42) to (TEMP-68).

[0082]

Chemical formula

[0083]

Chemical formula

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

[0085]

Chemical formula

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

[0087]

Chemical formula

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

[0089] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic group described herein is preferably a group of any of the following general formulas (TEMP-69) to (TEMP-102).

[0090]

Chemical formula

[0091]

Chemical formula

[0092]

Chemical formula

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

[0094]

Chemical formula

[0095]

Chemical formula

[0096] [Chemistry]

[0097] [Chemistry]

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

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

[0100] · "When combining to form a ring" In this specification, the case of "one or more sets of two or more adjacent ones combine with each other to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other" means the case of "one or more sets of two or more adjacent ones combine with each other to form a substituted or unsubstituted monocyclic ring", the case of "one or more sets of two or more adjacent ones combine with each other to form a substituted or unsubstituted condensed ring", and the case of "one or more sets of two or more adjacent ones do not combine with each other". Regarding the case in this specification where "one or more sets of two or more adjacent ones combine with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent ones combine with each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "the case of combining to form a ring"), the following will be described. Taking the case of an anthracene compound represented by the following general formula (TEMP-103) whose mother skeleton is an anthracene ring as an example.

[0101] [Chemistry]

[0102] For example, R921 ~R 930 In the case of "one or more sets consisting of two or more adjacent ones are combined with each other to form a ring", the set consisting of two adjacent ones that forms one set refers to R 921 and R 922 and the set of R 922 and R 923 and the set of R 923 and R 924 and the set of R 924 and R 930 and the set of R 930 and R 925 and the set of R 925 and R 926 and the set of R 926 and R 927 and the set of R 927 and R 928 and the set of R 928 and R 929 and the set of R, and R 929 and R 921 and the set of R.

[0103] The above "one or more sets" means that two or more sets consisting of two or more adjacent ones may simultaneously form a ring. For example, R 921 and R 922 are combined with each other to form ring Q A , and at the same time R 925 and R 926 are combined with each other to form ring Q B is formed. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0104]

Chemical formula

[0105] The case where a "set consisting of two or more adjacent ones" forms a ring includes not only the case where a set consisting of "two" adjacent ones is combined as in the above example, but also the case where a set consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form ring Q A , and R 922 and R923 are bonded to each other to form ring Q C to form, and a group consisting of three adjacent ones (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and condensed to the anthracene backbone. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C share R 922 .

[0106] [Chemical formula]

[0107] The "monocyclic ring" or "condensed ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "a set of two adjacent ones" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" can form a saturated ring or an unsaturated ring. For example, ring Q A and ring Q B formed in the general formula (TEMP-104) are each a "monocyclic ring" or "condensed ring", respectively. Also, ring Q A and ring Q C formed in the general formula (TEMP-105) are "condensed rings". Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring formed by the condensation of ring Q A and ring Q C . If ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is a monocyclic ring. If ring Q A in the general formula (TMEP-104) is a naphthalene ring, ring Q A is a condensed 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 "form a ring" means that a ring is formed only with a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more optional elements. For example, R 921 and R 922 and are bonded together to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 It means a ring formed by the carbon atom of the anthracene skeleton to which R is bonded and one or more arbitrary elements. 921 and R 922 Todekan Q A In the case where R 921 The carbon atom of the anthracene skeleton to which R is bonded 922 When the carbon atom of the anthracene skeleton to which R is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 and R 922 The ring formed by this is a benzene ring.

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

[0110] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. The above is the explanation for the case where "one or more sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" (the case of "bonding to form a ring").

[0111] · Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "any substituent" in the present specification) is, for example, An unsubstituted alkyl group having 1 to 50 carbon atoms, An unsubstituted alkenyl group having 2 to 50 carbon atoms, An unsubstituted alkynyl group having 2 to 50 carbon atoms, An unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), A halogen atom, a cyano group, a nitro group, An unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and A group selected from the group consisting of an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, etc., Here, R 901 ~R 907 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. When two or more R 901 are present, two or more R 901 are the same as or different from each other, When two or more R 902 are present, two or more R 902 are the same as or different from each other, When two or more R 903 are present, two or more R903 are identical to or different from each other, R 904 when two or more Rs are present, the two or more Rs 904 are identical to or different from each other, R 905 when two or more Rs are present, the two or more Rs 905 are identical to or different from each other, R 906 when two or more Rs are present, the two or more Rs 906 are identical to or different from each other, R 907 when two or more Rs are present, the two or more Rs 907 are identical to or different from each other.

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

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

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

[0115] Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably a benzene ring. Unless otherwise specified in this specification, any substituent may further have a substituent. The substituents that any substituent may further have are the same as the above-mentioned any substituent.

[0116] In this specification, the numerical range represented by "AA~BB" means a range including the numerical value AA described before "AA~BB" as the lower limit value and the numerical value BB described after "AA~BB" as the upper limit value.

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

[0118]

Chemical formula

[0119] (In the general formula (100A), R 101 ~R 112 One of them is a group represented by the general formula (100B), R other than the group represented by the general formula (100B) 101 ~R 112 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) 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 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 , R 902 , R 903 , R 904 , R 905 , R 801 and R 802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R 901 are the same as or different from each other, R 902 When there are a plurality of R 902 are the same as or different from each other, R 903 When there are a plurality of R 903 are the same as or different from each other, R 904 When there are a plurality of R 904 are the same as or different from each other, R 905 When there are a plurality of R 905 are the same as or different from each other, R 801 When there are a plurality of R 801 are the same as or different from each other, R802 When there are a plurality of R's 802 they are the same as or different from each other, In the general formula (100B), n101 is an integer of 0 or 1 or more, When n101 is an integer of 1 or more, L 101 is an unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, an arylene group having 10 to 50 ring-forming carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a divalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted, However, the arylene group having 6 to 50 ring-forming carbon atoms in the unsubstituted case is not a condensed ring, L 101 When there are two or more L's 101 they are the same as or different from each other, Ar 101 is 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 the general formula (100A), However, among R 101 ~R 112 in the general formula (100A), and L 101 and Ar 101 in the general formula (100B), at least any one of them has at least one deuterium atom. When only L 101 has a deuterium atom, 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 L 101 .)

[0120] In the present specification, the "condensed ring" represents a condensed aryl group (for example, naphthyl group, etc.) and a condensed heterocyclic group (for example, carbazolyl group, etc.).

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

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

[0123]

Chemical formula

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

[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-forming carbon atoms, or a heterocyclic group having 5 to 12 ring-forming atoms, and more preferably a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.

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

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

[0129] In the compound according to this embodiment, it is also preferable that L 101 is any group represented by the following general formulas (L101) to (L114). In the following examples, * indicates the bonding position.

[0130]

Chemical formula

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

[0132] In the compound according to this embodiment, Ar 101 is preferably an aryl group in which 4 or more rings, which may be substituted or unsubstituted, are fused, or a heterocyclic group in which 4 or more rings, which may be substituted or unsubstituted, are fused.

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

[0134] [Chemical formula]

[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-forming carbon atoms, an arylene group having 10 to 50 ring-forming carbon atoms in which 2 or more rings, which may be substituted or unsubstituted, are fused, or a divalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, provided that the unsubstituted arylene group having 6 to 50 ring-forming carbon atoms is not a condensed ring, When two or more L1 are present, the two or more L1 are the same as 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 sets of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted condensed ring, R51 ~R 54 、R 57 、and R 61 ~R 64 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, * indicates the bonding position to the benz[a]anthracene ring in the 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 sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted condensed ring R 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 and have the same meaning as * indicates the bonding position with the benz[a]anthracene ring in the general formula (100A), in the general formula (1B-3), R 51 ~R 55 , and R 81 ~R 84 one or more sets of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, and R 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 and have the same meaning as * indicates the bonding position with the benz[a]anthracene ring in the general formula (100A), in the general formula (1D), one of R 21 ~R 30 indicates the bonding position with the benz[a]anthracene ring in the general formula (100A), and for R in the general formula (1D) that is not at this bonding position 21 ~R 30 one or more sets of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, In the general formula (1D), R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring at the bonding position with the benz[a]anthracene ring in the general formula (100A). 21 ~R 30 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, In the groups represented by the general formulas (1B-1), (1B-2), (1B-3), and (1D), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , and R 907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R, the plurality of R 901 are the same as or different from each other, R 902 When there are a plurality of R, the plurality of R 902 are the same as or different from each other, R 903 When there are a plurality of R, the plurality of R 903 are the same as or different from each other, R 904 When there are a plurality of R, the plurality of R 904 are the same as or different from each other, R 905 When there are a plurality of R, the plurality of R 905 are the same as or different from each other, R 906 When there are a plurality of R, the plurality of R 906 are the same as or different from each other, R 907 When there are a plurality of R, the plurality of R 907 are the same as or different from each other.)

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

[0137] In the compound according to this embodiment, Ar 101 may not contain benzofluorene, benzoxanthene, and dibenzoxanthene.

[0138] In the compound according to this embodiment, R 101 ~R 112 and Ar 101 Among them, 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 preferable that any one of them 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 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 preferably a group represented by the general formula (100B). In the compound according to this embodiment, R 111 is preferably a group represented by the general formula (100B). R 105 , R 106 , R 107 , R 108 , R 111 , or R 112 is a group represented by the general formula (100B), whereby the excitation resistance of the compound according to this embodiment is likely to be improved, and the effect of extending the lifetime of the organic EL element is likely to be obtained.

[0141] In the compound according to this embodiment, it is also preferable that all of R 101 to R 110 and R 112 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] It is also preferable that the compound according to this embodiment is a compound represented by the following general formula (1A).

[0144] [Chemical]

[0145] (In the general formula (1A), R4 to R8 and R 10 ~R 12 One of them is a group represented by the general formula (1B), R1 to R3, R9, and R4 to R8 and R 10 ~R 12 except for the group represented by the general formula (1B) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 )-represented group, -COOR 802 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 、R 902 、R 903 、R 904 、R 905 、R801 and R 802 each independently is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R's, the plurality of R's 901 are the same as or different from each other, R 902 When there are a plurality of R's, the plurality of R's 902 are the same as or different from each other, R 903 When there are a plurality of R's, the plurality of R's 903 are the same as or different from each other, R 904 When there are a plurality of R's, the plurality of R's 904 are the same as or different from each other, R 905 When there are a plurality of R's, the plurality of R's 905 are the same as or different from each other, R 801 When there are a plurality of R's, the plurality of R's 801 are the same as or different from each other, R 802 When there are a plurality of R's, the plurality of R's 802 are the same as 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 of 1 or more, L1 is an unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted arylene group having 10 to 50 ring-forming carbon atoms in which two or more rings are condensed, or a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted, provided that the arylene group having 6 to 50 ring-forming carbon atoms in the unsubstituted case is not a condensed ring, When there are two or more L1s, the two or more L1s are the same as or different from each other. Ar1 is an aryl group in which four or more rings, which may be substituted or unsubstituted, are fused, or a heterocyclic group in which four or more rings, which may be substituted or unsubstituted, are fused, * indicates the bonding position to the benz[a]anthracene ring in the general formula (1A). However, among R1 to R 12 in the general formula (1A), and L1 and Ar1 in the general formula (1B), at least one of them has at least one deuterium atom. When only L1 has a deuterium atom, the deuterium atom is bonded to the ring directly bonded to the benz[a]anthracene ring among the rings constituting L1. )

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

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

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

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

[0150] In the compound according to this embodiment, it is also preferable that L1 is any group represented by the following general formulas (L1) to (L14). In the following examples, * indicates the bonding position.

[0151] [Chemical]

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

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

[0154] [Chemical]

[0155] (In the groups represented by the general formulas (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-forming carbon atoms, an arylene group having 10 to 50 ring-forming carbon atoms in which two or more substituted or unsubstituted rings are condensed, or a divalent heterocyclic group having 5 to 50 ring-forming atoms which is substituted or unsubstituted, provided that the unsubstituted arylene group having 6 to 50 ring-forming carbon atoms is not a condensed ring, When two or more L1 are present, the two or more L1 are the same as 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 sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 51 ~R 54 、R 57 、and R 61 ~R 64 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming 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 halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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 sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 51 ~R 53 、R 56 、R 57 、and R 71 ~R 74 are each independently the same as R 51 ~R 54 、R 57 、and R 61 ~R 64 in the general formula (1B-1), and * indicates the bonding position with 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 sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 51 ~R 55 、and R 81 ~R 84 are each independently the same as R 51 ~R 54 、R 57 、and R 61 ~R 64 in the general formula (1B-1), and * indicates the bonding position with the benz[a]anthracene ring in the general formula (1A), in the general formula (1D), one of R 21 ~R 30 indicates the bonding position with the benz[a]anthracene ring in the general formula (1A), and for R in the general formula (1D) that is not at the bonding position 21 ~R 30 one or more sets of two or more adjacent ones among them are Combine with each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, At the bonding position with the benz[a]anthracene ring in the general formula (1A), instead of forming the substituted or unsubstituted monocyclic ring, and not forming the substituted or unsubstituted condensed ring, R in the general formula (1D) 21 ~R 30 Are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, In the groups represented by the general formulas (1B-1), (1B-2), (1B-3), and (1D), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , and R 907 Are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, an aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or a heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, R 901 When there are a plurality of R's, the plurality of R's 901 are the same as or different from each other, R 902 When there are a plurality of R's, the plurality of R's 902 are the same as or different from each other, R 903 When there are a plurality of R's, the plurality of R's 903 are the same as or different from each other, R 904 When there are a plurality of R's, the plurality of R's 904 are the same as or different from each other, R 905 When there are a plurality of R's, the plurality of R's 905 are the same as or different from each other, R 906 When there are a plurality of R's, the plurality of R's 906 are the same as or different from each other, R 907 When there are a plurality of R's, the plurality of R's 907 are the same as or different from each other.)

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

[0157] In the compound according to this embodiment, Ar1 may not contain benzofluorene, benzoxanthene, and dibenzoxanthene.

[0158] In the compound according to this embodiment, at least one of R1 to R 12 and Ar1 preferably has at least one deuterium atom.

[0159] In the compound according to this embodiment, it is also preferable that at least any one of R1 to R 12 is a deuterium atom.

[0160] In the compound according to this embodiment, it is also preferable that R5, R6, R7, R8, R 11 , or R 12 is a group represented by the general formula (1B). In the compound according to this embodiment, it is also preferable that R6, R7, R 11 , or R 12 is a group represented by the general formula (1B). In the compound according to this embodiment, it is also preferable that R 11 is a group represented by the general formula (1B). R5, R6, R7, R8, R 11 , or R 12 which is a position with a higher electron density of HOMO and LUMO or a site where the singlet energy S1 is smaller, being a group represented by the general formula (1B) makes it easier to improve the excitation resistance of the compound according to this embodiment and easier to obtain the effect of extending the lifespan of the organic EL element.

[0161] In the compound according to this embodiment, it is also preferable that both R1 to R 10 and R 12 are deuterium atoms.

[0162] In the compound according to this embodiment, it is also preferable that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups, and all 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. Also, the compound according to this embodiment can be produced by following the synthesis method and using known alternative reactions and raw materials adapted to the target product.

[0164] · Specific examples of the compound according to this embodiment Specific examples of the compound according to this embodiment include, for example, 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 the chemical formula, a hydrogen atom is represented as H or the description is omitted.

[0165]

Chemical formula

[0166]

Chemical formula

[0167]

Chemical formula

[0168]

Chemical formula

[0169]

Chemical formula

[0170]

Chemical formula

[0171]

Chemical formula

[0172]

Chemical formula

[0173]

Chemical formula

[0174]

Chem.

[0175]

Chem.

[0176]

Chem.

[0177]

Chem.

[0178]

Chem.

[0179]

Chem.

[0180]

Chem.

[0181]

Chem.

[0182]

Chem.

[0183]

Chem.

[0184]

Chem.

[0185]

Chem.

[0186]

Chem.

[0187]

Chem.

[0188]

Chem.

[0189]

Chem.

[0190]

Chem.

[0191]

Chem.

[0192]

Chem.

[0193]

Chem.

[0194]

Chem.

[0195] [Chemical]

[0196] [Chemical]

[0197] [Chemical]

[0198] [Chemical]

[0199] [Chemical]

[0200] [Chemical]

[0201] [Chemical]

[0202] [Chemical]

[0203] [Chemical]

[0204] [Chemical]

[0205] [Chemical]

[0206]

Chem.

[0207]

Chem.

[0208]

Chem.

[0209]

Chem.

[0210]

Chem.

[0211]

Chem.

[0212]

Chem.

[0213]

Chem.

[0214]

Chem.

[0215]

Chem.

[0216]

Chem.

[0217]

Chem.

[0218]

Chem.

[0219]

Chem.

[0220]

Chem.

[0221]

Chem.

[0222]

Chem.

[0223]

Chem.

[0224]

Chem.

[0225]

Chem.

[0226]

Chem.

[0227] [Chemistry]

[0228] [Chemistry]

[0229] [Chemistry]

[0230] [Chemistry]

[0231] [Chemistry]

[0232] [Chemistry]

[0233] [Chemistry]

[0234] [Chemistry]

[0235] [Chemistry]

[0236] [Chemistry]

[0237] [Chemistry]

[0238]

Chem.

[0239]

Chem.

[0240]

Chem.

[0241]

Chem.

[0242]

Chem.

[0243] Incidentally, as novel deuterium compounds similar to the compound represented by the general formula (100A) and the compound represented by the general formula (1A), there are, for example, the following structures.

[0244]

Chem.

[0245]

Chem.

[0246] The compound according to the present embodiment has a high carrier resistance or an effect of stabilizing the excited state because a deuterium atom is bonded to at least one of the benz[a]anthracene ring, the linker (L1 or L 101 ) directly bonded to the benz[a]anthracene ring, and Ar1 or Ar 101 . Therefore, according to the compound of the present embodiment, an increase in the lifetime of the organic EL element can be expected. In particular, the benzene[a]anthracene ring and Ar1 or Ar having low singlet energy S1 and triplet energy T1 that are the centers of the excited state 101 can be expected to have a longer lifespan by bonding deuterium atoms thereto.

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

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

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

[0250] The organic EL element according to this embodiment has an anode, a cathode, and 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 preferably contains a first compound represented by the general formula (100A), and the second light-emitting layer preferably contains a second compound.

[0251] The organic EL element according to this embodiment has an anode, a cathode, and 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. It is also preferable that the first light-emitting layer contains a first compound represented by the general formula (1A), and the second light-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 can, for example, have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order. However, the order of the first light-emitting layer and the second light-emitting layer can be reversed, and it can also 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 element according to this embodiment includes a 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, it is also preferable that the organic EL element according to this embodiment includes a first light-emitting layer between the anode and the cathode, and the second light-emitting layer is disposed between the anode and the first light-emitting layer.

[0254] (Emission wavelength of the organic EL element) The organic EL element according to this embodiment preferably emits light with a maximum peak wavelength of 500 nm or less during element driving, and more preferably emits light with a wavelength of 430 nm or more and 480 nm or less. The measurement of the maximum peak wavelength of the light emitted by the organic EL element during element driving is performed as follows. When a voltage is applied to the organic EL element so that the current density is 10 mA / cm 2 The spectral emission luminance spectrum is measured with a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta). In the obtained spectral emission luminance spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is measured, and this is taken as the maximum peak wavelength (unit: nm).

[0255] The method for measuring the maximum peak wavelength of the compound in this specification is as follows. A toluene solution of the compound to be measured with a concentration of 10 -6 mol / L or more and 10 -5 mol / L or less is prepared and placed in a quartz cell, and the emission spectrum of this sample (vertical axis: emission intensity, horizontal axis: wavelength) is measured at room temperature (300K). The emission spectrum can be measured by a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech 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 with the maximum emission intensity is defined as the maximum emission peak wavelength. Note that in this specification, the maximum peak wavelength may sometimes be referred to as the fluorescence emission maximum peak wavelength (FL-peak).

[0256] In the organic EL element according to this embodiment, the organic layer may be composed of only the light-emitting layer, but as the organic layer, for example, it may further have at least any 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 barrier layer, and an electron barrier layer.

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

[0258] In the organic EL element according to this embodiment, it is preferable to have an electron transport layer between the cathode and the light-emitting region. In the organic EL element according to this embodiment, when the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the lamination order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is preferable to have an electron transport layer between the cathode and the second light-emitting layer. Further, when the lamination order of the first light-emitting layer and the second light-emitting layer is the order of the second light-emitting layer and the first light-emitting layer from the anode side, 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 the organic EL element according to this embodiment. The organic EL element 1A shown in Fig. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A includes a hole transport band 6, a light-emitting region 5A, and an electron transport band 7 in this order from the anode 3 side. The hole transport band 6 includes a hole injection layer 61 and a hole transport layer 62 in this order from the anode 3 side. The light-emitting region 5A includes one light-emitting layer 5. The electron transport band 7 includes an electron transport layer 71 and an electron injection layer 72 in this order from the light-emitting region 5A side.

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

[0261] (Light-emitting compound) In the organic EL element 1A, it is also preferable that the light-emitting layer 5 further contains a light-emitting compound (preferably a fluorescent light-emitting compound).

[0262] The light-emitting compound contained in the light-emitting 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), One or more compounds selected from the group consisting of a compound represented by the following general formula (9), and a compound represented by the following general formula (10).

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

[0264] [Chemical formula]

[0265] (In the above general formula (3), R 301 ~R 310 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 301 ~R 310 at least one of them is a monovalent group represented by the following general formula (31), R that does not form the monocyclic ring, does not form the condensed ring, and is not a monovalent group represented by the following general formula (31) 301 ~R 310 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )

[0266]

Chemical formula

[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-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L 301 ~L 303 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, * indicates the bonding position in 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 a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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-forming carbon atoms, R 901 when there are a plurality of them, the plurality of Rs 901 are the same as or different from each other, R 902 when there are a plurality of them, the plurality of Rs 902 are the same as or different from each other, R 903 when there are a plurality of them, the plurality of Rs 903 are the same as or different from each other, R 904 when there are a plurality of them, the plurality of Rs 904 are the same as or different from each other, R 905 when there are a plurality of them, the plurality of Rs 905 are the same as or different from each other, R 906 when there are a plurality of them, the plurality of Rs 906 are the same as or different from each other, R 907 when there are a plurality of them, the plurality of Rs 907 are the same as or different from each other.

[0269] In the general formula (3), it is preferable that two of R 301 ~R 310 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]

Chemical formula

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

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

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

[0275]

Chemical formula

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

[0277]

Chemical formula

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

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

[0280] [Chemical formula]

[0281] (In the general formula (36), X3 represents an oxygen atom or a sulfur atom, R 321 ~R 327 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the monocyclic ring and not forming the condensed ring, R 321 ~R 327 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, * is L 302, L 303 , L 312 , L 313 , L 315 or L 316 indicates the bonding position with.)

[0282] X3 is preferably an oxygen atom.

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

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

[0286] [Chemical formula]

[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 and have the same meaning, R 321 ~R 327 and one or more sets of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, R 341 ~R 347 and one or more sets of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, do not form the monocyclic ring and do not form the condensed ring, R 321 ~R 327 as well as R 341 ~R 347 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R906 )(R 907 ) group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 331 ~R 335 and R 351 ~R 355 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group, -O-(R 904 ) group, -S-(R 905 ) group, -N(R 906 )(R 907 ) group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

[0288] Examples of the compound represented by the general formula (3) include, for example, the following compounds as specific examples.

[0289]

Chemical formula

[0290]

Chemical formula

[0291] [Chemical]

[0292] [Chemical]

[0293] [Chemical]

[0294] (Compound represented by General Formula (4)) The compound represented by General Formula (4) will be described.

[0295] [Chemical]

[0296] (In the general formula (4), Z is each independently CRa or a nitrogen atom, The A1 ring and the A2 ring are each independently, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms, When there are a plurality of Ra, one or more of the sets consisting of two or more adjacent ones among the plurality of Ra are, Bonded to each other to form a substituted or unsubstituted monocyclic ring, Bonded to each other to form a substituted or unsubstituted condensed ring, or Do not bond to each other, n21 and n22 are each independently 0, 1, 2, 3 or 4, When there are a plurality of Rb, one or more of the sets consisting of two or more adjacent ones among the plurality of Rb are, Bonded to each other to form a substituted or unsubstituted monocyclic ring, Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, When there are a plurality of Rc, one or more of the groups consisting of two or more adjacent ones among the plurality of Rc are, Combine with each other to form a substituted or unsubstituted monocyclic ring, Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, Ra, Rb and Rc that do not form the monocyclic ring and do not form the condensed ring 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-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

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

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

[0301] Among Ra, Rb and Rc, it is preferable that at least one is a group represented by the following general formula (4a), and it is more preferable that at least two are groups represented by the following general formula (4a).

[0302]

Chemical formula

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

[0304] [Chemical formula]

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

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

[0307] [Chemical formula]

[0308] (In the general formula (42), R 401 ~R 411 one or more sets of two or more adjacent ones among them are Combine with each other to form a substituted or unsubstituted monocyclic ring, Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, Do not form the monocyclic ring and do not form the condensed ring, R 401 ~R 411 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

[0309] R 401 ~R 411 Among them, 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 are preferably groups 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. Also, 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 they are bonded.

[0311] [Chemical formula]

[0312] (In the general formula (4-1), the two *s are each independently bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring as the A1 ring of the general formula (4) or a ring-forming atom of the heterocyclic ring, or to any one of R 404 ~R 407 and are bonded to any one of them, The three *s in the general formula (4-2) are each independently bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring as the A1 ring of the general formula (4) or a ring-forming atom of the heterocyclic ring, or to any one of R 404 ~R 407 and are bonded to any one of them, R 421 ~R 427 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, R 431 ~R 438 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, do not form the monocyclic ring and do not form the condensed ring, R 421 ~R 427and R 431 ~R 438 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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]

Chemical formula

[0315]

Chemical formula

[0316]

Chemical formula

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

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

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

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

[0321]

Chemical formula

[0322]

Chemical formula

[0323]

Chemical formula

[0324]

Chem.

[0325]

Chem.

[0326] (In the general formulas (461), (462), (463), (464), (465), (466), and (467), R 421 ~R 427 are each independently the same as R 421 ~R 427 in the general formula (4-1), R 431 ~R 438 are each independently the same as R 431 ~R 438 in the general formula (4-2), R 440 ~R 448 and R 451 ~R 454 are each independently the same as R 401 ~R 411 in the general formula (42), X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ), R 801 、R 802 and R 803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, R 801 When there are a plurality of R's, the plurality of R's 801 are the same as or different from each other, R 802 When there are a plurality of R's, the plurality of R's 802 are the same as or different from each other, R 803 When there are a plurality of R's, the plurality of R's 803 are the same as or different from each other.)

[0327] In one embodiment, the compound represented by the general formula (42) is such that one or more sets of two or more adjacent ones among R 401 ~R 411 are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring. This embodiment will be described in detail as a compound represented by the following general formula (45).

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

[0329] [Chemical formula]

[0330] (In the general formula (45), the pair consisting of R 461 and R 462 , the pair consisting of R 462 and R 463 , the pair consisting of R 464 and R 465 , the pair consisting of R 465 and R 466 , the pair consisting of R 466 and R 467 , the pair consisting of R 468 and R 469 the pair consisting of R469 and R 470 a pair consisting of and R, and R 470 and R 471 Among the pairs selected from the group consisting of pairs consisting of and R, two or more are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring, provided that R 461 and R 462 a pair consisting of and R and R 462 and R 463 a pair consisting of and R; R 464 and R 465 a pair consisting of and R and R 465 and R 466 a pair consisting of and R; R 465 and R 466 a pair consisting of and R and R 466 and R 467 a pair consisting of and R; R 468 and R 469 a pair consisting of and R and R 469 and R 470 a pair consisting of and R; and R 469 and R 470 a pair consisting of and R and R 470 and R 471 a pair consisting of and R do not form a ring simultaneously, R 461 ~R 471 Two or more rings formed by are the same as or different from each other, R that does not form the monocyclic ring and does not form the condensed ring 461 ~R 471 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 ) group, -S-(R 905 ) group, -N(R 906 )(R 907 ) group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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, and together with two ring-forming carbon atoms to which R n and R n+1 are bonded, form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed 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, more preferably 5 or 6.

[0332] The number of the above ring structures in the compound represented by the general formula (45) is, for example, 2, 3, or 4. Two or more ring structures may be present on the same benzene ring of the parent skeleton of the general formula (45), or may be present on different benzene rings. For example, when having 3 ring structures, one ring structure may be present on each of the 3 benzene rings of the general formula (45).

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

[0334]

Chemical formula

[0335] (In the general formulas (451) to (457), each of *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represents n two ring-forming carbon atoms to which R n+1 is bonded, the ring-forming carbon atom to which R n 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 sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the monocyclic ring and not forming the condensed ring, and R 4501 ~R 4514 are each independently synonymous with R 461 ~R 471 in the general formula (45).)

[0336]

Chemical Formula

[0337] (In the general formulas (458) to (460), each of *1 and *2, and *3 and *4 represents n two ring-forming carbon atoms to which R n+1 is bonded, the ring-forming carbon atom to which R n is bonded may be either of the two ring-forming 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, and R 4512 ~R 4513 and R 4515 ~R 4525 in which at least one set of two or more adjacent ones of them are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the monocyclic ring and not forming the condensed ring, R 4512 ~R 4513 , R 4515 ~R 4521 and R 4522 ~R 4525 , and R 4514 are each independently synonymous with R 461 ~R 471 in the general formula (45).)

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

[0339] (i) In the general formula (45), the substituents when the ring structure formed by R n and R n+1 has substituents, (ii) In the general formula (45), R 461 ~R 471 that do not form a ring structure, and (iii) R 4501 ~R 4514 , R 4515 ~R4525 is preferably, each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -N(R 906 )(R 907 ), or a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or any group selected from the group consisting of groups represented by the following general formulas (461) to (464).

[0340]

Chemical formula

[0341] (In the general formulas (461) to (464), R d is, each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), or a group represented by -O-(R 904 ), or a group represented by -S-(R 905 ), or a group represented by -N(R 906 )(R 907 ), or a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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 a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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-forming carbon atoms, R 801 when there are a plurality of R 801 the plurality of R R 802 when there are a plurality of R 802 the plurality of R R 803 when there are a plurality of R 803 the plurality of R p1 is 5, p2 is 4, p3 is 3, p4 is 7, * in the general formulas (461) to (464) each independently indicates the bonding position to the ring structure.) In the luminescent compound, R 901 ~R 907 are as defined above.

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

[0343]

Chemical formula

[0344]

Chemical formula

[0345] (In the general formulas (45-1) to (45-6), rings d to i are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring, R 461 ~R 471 are each independently the same as R 461 ~R 471 in the general formula (45).)

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

[0347]

Chemical formula

[0348]

Chemical formula

[0349] (In the general formulas (45-7) to (45-12), rings d to f, k, j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring, R 461 ~R 471 are each independently the same as R 461 ~R 471 in the general formula (45).)

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

[0351] [Chemical formula]

[0352] [Chemical formula]

[0353] [Chemical formula]

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

[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-forming carbon atoms, the group represented by the general formula (461), the group represented by the general formula (463), or 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 formulas (45-22) to (45-25).

[0357] [Chemical]

[0358] (In the general formulas (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 as well as R 481 ~R 488 are each independently the same as R 461 ~R 471 in the general formula (45). R 801 R 802 and R 803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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-forming carbon atoms, R 801 When there are a plurality of R 801 they may be the same as or different from each other, R 802 When there are a plurality of R 802 they may be the same as or different from each other, R 803 When there are a plurality of R 803 they may be the same as or different from each other.)

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

[0360]

Chemical formula

[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 synonymous with R 461 ~R 471 in the general formula (45). R 801 , R 802 and R 803 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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-forming carbon atoms, R 801 when there are a plurality of R 801 s, the plurality of R R 802 when there are a plurality of R 802 s, the plurality of R R 803When there are a plurality of R's, the plurality of R's 803 are the same as or different from each other.)

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

[0363]

Chemical formula

[0364]

Chemical formula

[0365]

Chemical formula

[0366]

Chemical formula

[0367]

Chemical formula

[0368]

Chemical formula

[0369]

Chemical formula

[0370]

Chemical formula

[0371]

Chemical formula

[0372] [Chemical formula]

[0373] (Compound represented by general formula (5)) The compound represented by general formula (5) will be described. The compound represented by general formula (5) is a compound corresponding to the compound represented by the above-mentioned general formula (41-3).

[0374] [Chemical formula]

[0375] (In the general formula (5), R 501 ~R 507 and R 511 ~R 517 one or more sets of two or more adjacent sets among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the monocyclic ring and not forming the condensed ring, R 501 ~R 507 and R 511 ~R 517 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R905 a group represented by -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. R 521 and R 522 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

[0376] "One set of a group consisting of two or more adjacent ones among "R 501 ~R 507 and R 511 ~R 517 ", for example, a set consisting of R 501 and R 502 , a set consisting of R 502 and R 503 , a set consisting of R 503 and R504 a group consisting of, R 505 and R 506 a group consisting of, R 506 and R 507 a group consisting of, R 501 and R 502 and R 503 a combination such as a group consisting of, etc.

[0377] In one embodiment, R 501 ~R 507 and R 511 ~R 517 at least one, preferably two of them are groups represented by -N(R 906 )(R 907 ).

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

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

[0380]

Chemical formula

[0381] (In the general formula (52), R 531 ~R 534 and R 541 ~R 544 one or more groups consisting of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, R that does not form the single ring and does not form the condensed ring 531 ~R 534 、R 541 ~R 544 、and R 551 and R 552 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 561 ~R 564 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

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

[0383]

Chemical formula

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

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

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

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

[0388] As the compound represented by the general formula (5), for example, the following compounds can be cited as specific examples.

[0389]

Chemical formula

[0390]

Chemical formula

[0391]

Chemical formula

[0392]

Chemical formula

[0393]

Chemical formula

[0394] [Chemistry]

[0395] [Chemistry]

[0396] [Chemistry]

[0397] [Chemistry]

[0398] [Chemistry]

[0399] [Chemistry]

[0400] [Chemistry]

[0401] [Chemistry]

[0402] [Chemistry]

[0403] [Chemistry]

[0404] [Chemistry]

[0405] [Chemical formula]

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

[0407] [Chemical formula]

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

[0409] The a-ring, b-ring, and c-ring are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring-forming carbon atoms or substituted or unsubstituted heterocyclic rings having 5 to 50 ring-forming atoms) that are 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 ring" of the a-ring, b-ring, and c-ring has the same structure as the compound obtained by introducing a hydrogen atom into the above-mentioned "aryl group". The "aromatic hydrocarbon ring" of the a-ring contains three carbon atoms on the central fused bicyclic structure of the general formula (6) as ring-forming atoms. The "aromatic hydrocarbon ring" of the b-ring and c-ring contains two carbon atoms on the central fused bicyclic structure of the general formula (6) as ring-forming atoms.

[0411] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms" include compounds obtained by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1. The "heterocyclic ring" of the a-ring, b-ring, and c-ring has the same structure as the compound obtained by introducing a hydrogen atom into the above-mentioned "heterocyclic group". The "heterocyclic ring" of the a-ring contains three carbon atoms on the central fused bicyclic structure of the general formula (6) as ring-forming atoms. The "heterocyclic ring" of the b-ring and c-ring contains two carbon atoms on the central fused bicyclic structure of the general formula (6) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms" include compounds obtained by introducing a hydrogen atom into the "heterocyclic group" described in Specific Example Group G2.

[0412] R 601 and R 602 may each independently be bonded to the a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocyclic ring. The heterocyclic ring in this case contains a nitrogen atom on the central fused bicyclic structure of the general formula (6). The heterocyclic ring in this case may contain a heteroatom other than the nitrogen atom. R 601 and R 602 being bonded to the a-ring, b-ring, or c-ring specifically means that R 601 and R 602means that the atoms constituting it are bonded. For example, R 601 is bonded to the a-ring, and a bicyclic fused (or tricyclic fused or higher) nitrogen-containing heterocyclic ring in which the ring containing R 601 is fused with the a-ring may be formed. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the bicyclic fused or higher heterocyclic groups containing nitrogen among the specific example group G2 and the like. R 601 When it is bonded to the b-ring, when R 602 is bonded to the a-ring, and when R 602 is bonded to the c-ring, it is the same as above.

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

[0414] In one embodiment, R 601 and R 602 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

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

[0416]

Chemical formula

[0417] (In the general formula (62), R 601A is R 611 and R 621Selected from the group consisting of one or more and combined to form a substituted or unsubstituted heterocyclic ring, or without forming a substituted or unsubstituted heterocyclic ring, R 602A is R 613 and R 614 Selected from the group consisting of one or more and combined to form a substituted or unsubstituted heterocyclic ring, or without forming a substituted or unsubstituted heterocyclic ring, R that does not form the substituted or unsubstituted heterocyclic ring 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 611 ~R 621 One or more sets of two or more adjacent ones among Combine with each other to form a substituted or unsubstituted monocyclic ring, Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, Do not form the substituted or unsubstituted heterocyclic ring, do not form the monocyclic ring, and do not form the condensed ring R 611 ~R 621 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted 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-forming 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 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

[0418] R in the general formula (62) 601A and R 602A are each a group corresponding to R 601 and R 602 in the general formula (6). For example, R 601A and R 611 may be bonded to form a nitrogen-containing heterocyclic ring in which the ring containing them and the benzene ring corresponding to the a-ring are condensed (or a tricyclic or higher condensed ring). Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the heterocyclic groups having two or more condensed rings containing nitrogen among the specific example group G2. When R 601A and R 621 are bonded, when R 602A and R 613 are bonded, and when R 602A and R 614 are bonded, the situation is the same as above.

[0419] R 611 ~R 621 One or more sets of two or more adjacent ones among may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring. For example, R 611 and R 612combine, and for the 6-membered ring to which they are attached, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like may be condensed to form a structure, and the formed condensed ring becomes 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 a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

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

[0422] 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.

[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, and 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]

Chemical formula

[0426] (In the general formula (63), R 631 combines with R 646 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring, R 633 combines with R 647 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring, R 634 combines with R 651 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring, R 641 combines with R 642 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring, R 631 ~R 651 Among them, one or more sets of two or more adjacent ones combine with each other to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form the substituted or unsubstituted heterocyclic ring, do not form the monocyclic ring, and do not form the condensed ring. R 631 ~R 651 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A cycloalkyl group having 3 to 50 carbon atoms in the ring, which may or may not be substituted, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by A halogen atom, A cyano group, A nitro group, An aryl group having 6 to 50 carbon atoms in the ring, which may or may not be substituted, or A heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted.)

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

[0428] In one embodiment, R 631 ~R 651 which do not contribute to ring formation are each independently A hydrogen atom, An alkyl group having 1 to 50 carbon atoms, which may or may not be substituted, An aryl group having 6 to 50 carbon atoms in the ring, which may or may not be substituted, or A heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted.)

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

[0430] 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.

[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 which 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]

Chemical formula

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

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

[0436] In one embodiment, R 661 ~R 665 each independently is 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]

Chemical formula

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

Chemical formula

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

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

[0444] In one embodiment, R 672 is A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, -N(R 906 )(R 907 )-represented group, or A substituted or unsubstituted aryl group having 6 to 50 ring-forming 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 )-represented group, or A substituted or unsubstituted aryl group having 6 to 50 ring-forming 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]

Chemical formula

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

Chemical formula

[0450] (In the general formula (63C’), R 683 ~R 686 are each independently the same as R 683 ~R 686 in the general formula (63C).)

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

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

[0453] The compound represented by the general formula (6) is first reacted to produce an intermediate by bonding the a-ring, b-ring, and c-ring with a linking group (a group containing N-R 601 group and a group containing N-R 602 group) (the first reaction), and the final product can be produced by bonding the a-ring, b-ring, and c-ring with a linking group (a group containing a boron atom) (the second reaction). In the first reaction, an amination reaction such as the Buchwald-Hartwig reaction can be applied. In the second reaction, a tandem hetero Friedel-Crafts reaction or the like can be applied.

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

[0455]

Chem.

[0456]

Chem.

[0457]

Chem.

[0458]

Chem.

[0459]

Chem.

[0460]

Chem.

[0461]

Chem.

[0462]

Chem.

[0463]

Chem.

[0464]

Chem.

[0465]

Chem.

[0466]

Chem.

[0467]

Chem.

[0468]

Chem.

[0469]

Chem.

[0470]

Chem.

[0471]

Chem.

[0472] [Chemical formula]

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

[0474] [Chemical formula]

[0475] [Chemical formula]

[0476] (In the general formula (7), the r-ring is a ring represented by the general formula (72) or general formula (73) that condenses at any position of the adjacent ring, the q-ring and the s-ring are each independently a ring represented by the general formula (74) that condenses at any position of the adjacent ring, the p-ring and the t-ring are each independently a structure represented by the general formula (75) or general formula (76) that condenses at any position of the adjacent ring, X7 is an oxygen atom, a sulfur atom, or NR 702 . R 701 When there are multiple Rs, 701 adjacent multiple Rs either bond to each other to form a substituted or unsubstituted monocyclic ring, bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, Rs that do not form the monocyclic ring and do not form the condensed 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 cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L 701 is 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-forming carbon atoms, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, m1 is 0, 1 or 2, m2 is 0, 1, 2, 3 or 4, m3 is, independently of each other, 0, 1, 2 or 3, m4 is, independently of each other, 0, 1, 2, 3, 4 or 5, R 701 When there are a plurality of R 701 are the same as or different from each other, When there are a plurality of X7, the plurality of X7 are the same as or different from each other, R 702 When there are a plurality of R 702 are the same as or different from each other, Ar 701 When there are a plurality of Ar 701 are the same as or different from each other, Ar 702 When there are a plurality of Ar 702 are the same as or different from each other, L 701 When there are a plurality of L 701 are the same as or different from each other.)

[0477] In the general formula (7), each of the p-ring, q-ring, r-ring, s-ring and t-ring condenses by sharing two carbon atoms with an adjacent ring. The condensation position and orientation are not limited, and condensation can occur at any position and orientation.

[0478] In one embodiment, in the general formula (72) or general formula (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 formulas (71-1) to (71-6).

[0480]

Chemical formula

[0481]

Chemical formula

[0482]

Chem.

[0483]

Chem.

[0484]

Chem.

[0485]

Chem.

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

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

[0488]

Chem.

[0489]

Chem.

[0490]

Chem.

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

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

[0493]

Chemical formula

[0494]

Chemical formula

[0495]

Chemical formula

[0496]

Chemical formula

[0497]

Chemical formula

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

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

[0500]

Chemical formula

[0501]

Chemical formula

[0502]

Chemical formula

[0503] (In the general formulas (71-31) to (71-33), R 701 、 X7, Ar 701 、 Ar 702 、 L 701 、 m2 to m4 are, respectively, R in the general formula (7) 701 、 X7, Ar 701 、 Ar 702 、 L 701 、 m2 to m4 and 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-forming carbon atoms.

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

[0506] Examples of the compound represented by the general formula (7) include the following compounds.

[0507]

Chemical formula

[0508]

Chemical formula

[0509]

Chemical formula

[0510]

Chemical formula

[0511]

Chemical formula

[0512]

Chemical formula

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

[0514]

Chemical formula

[0515] (In the general formula (8), R 801 and R 802 , R 802 and R 803 , and R 803 and R 804At least one set of them is combined with each other 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 set of them is combined with each other to form a divalent group represented by the following general formula (83).)

[0516]

Chemical formula

[0517] (R that does not form the divalent group represented by the general formula (82) 801 ~R 804 、and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84), R that does not form the divalent group represented by the general formula (83) 805 ~R 808 、and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84), X8 is an oxygen atom, a sulfur atom, or NR 809 wherein, R that does not form the divalent groups represented by the general formula (82) and general formula (83), and is not the monovalent group represented by the general formula (84) 801 ~R 808 、R that is not the monovalent group represented by the general formula (84) 811 ~R 814 and R 821 ~R 824 、and R 809 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

[0518]

Chemical formula

[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-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L 801 ~L 803 are each independently, a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or a divalent linking group formed by bonding of 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming 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 where 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 can form the group at possible positions.

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

[0522]

Chemical formula

[0523]

Chemical formula

[0524]

Chemical formula

[0525] (In the general formulas (81-1) to (81-6), X8 has the same meaning as X8 in the general formula (8), R 801 ~R 824 at least two of them are monovalent groups represented by the general formula (84), R that is not the monovalent group represented by the general formula (84) 801 ~R 824 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a halogen atom a cyano group a nitro group a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

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

[0527]

Chemical formula

[0528]

Chemical formula

[0529]

Chemical formula

[0530]

Chemical formula

[0531]

Chemical formula

[0532]

Chemical formula

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

[0534] R that does not form the divalent group represented by the general formula (82) or the general formula (83) and is not the monovalent group represented by the general formula (84) 801 ~R 808 , and R that is not the monovalent group represented by the general formula (84) 811 ~R 814 and R 821 ~R 824 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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]

Chemical formula

[0537] (In the general formula (85), R 831 ~R840 is, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, wherein * in the general formula (85) has the same meaning as * in the general formula (84).)

[0538]

Chemical formula

[0539] (In the general formula (86), Ar 801 , L 801 and L 803 have the same meaning as Ar 801 , L 801 and L 803 in the general formula (84), HAr 801 has a structure represented by the following general formula (87).)

[0540]

Chemical formula

[0541] (In the general formula (87), X 81 is an oxygen atom or a sulfur atom, R 841 ~R 848 any one of them is a single bond connecting to L 803 and the R not being a single bond 841 ~R 848 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

[0542] As the compound represented by the general formula (8), in addition to the compounds described in International Publication No. 2014 / 104144, for example, the following compounds can be cited as specific examples.

[0543]

Chemical formula

[0544] [Chemical]

[0545] [Chemical]

[0546] [Chemical]

[0547] [Chemical]

[0548] [Chemical]

[0549] (Compound represented by General Formula (9)) The compound represented by General Formula (9) will be described.

[0550] [Chemical]

[0551] (In the above General Formula (9), A 91 ring and A 92 rings are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms, A 91 ring and A 92 one or more rings selected from the group consisting of rings are bonded to the * of the structure represented by the following General Formula (92).)

[0552] [Chemical]

[0553] (In the general formula (92), A 93 the ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming 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 are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the monocyclic ring and not forming the condensed ring, R 91 and R 92 , and R 93 ~R 99 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, A halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

[0554] A 91 ring and A 92 One or more rings selected from the group consisting of rings are bonded to * of the structure represented by the general formula (92). That is, in one embodiment, A 91 The ring-forming carbon atom of the aromatic hydrocarbon ring of the A ring or the ring-forming atom of the heterocyclic ring is bonded to *. Further, in one embodiment, A 92 The ring-forming carbon atom of the aromatic hydrocarbon ring of the A ring or the ring-forming atom of the heterocyclic ring is bonded to *.

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

[0556]

Chemical formula

[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-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L 91 ~L 93 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or A divalent linking group formed by linking 2 to 4 selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, In the general formula (93), * is A 91 Ring and A 92 Indicates the bonding position with either of the rings.)

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

[0559] In one embodiment, R 91 And R 92 Are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming 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-forming 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-forming carbon atoms, for example, a substituted or unsubstituted benzene ring. In one embodiment, X9 is an oxygen atom or a sulfur atom.

[0562] Examples of the compound represented by the general formula (9) include the following compounds as specific examples.

[0563]

Chemical formula

[0564] [Chemical]

[0565] [Chemical]

[0566] [Chemical]

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

[0568] [Chemical]

[0569] [Chemical]

[0570] (In the general formula (10), The Ax1 ring is a ring represented by the general formula (10a) that condenses at any position of the adjacent ring, The Ax2 ring is a ring represented by the general formula (10b) that condenses at any position of the adjacent ring, The two * in the general formula (10b) are bonded to any position 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-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms, Ar 1001 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 1001 ~R 1006 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, mx1 is 3 and mx2 is 2, a plurality of R 1001 are the same as or different from each other, a plurality of R 1002 are the same as or different from each other, ax is 0, 1 or 2, when ax is 0 or 1, the structures within the parentheses indicated by "3 - ax" are the same as or different from each other, when ax is 2, a plurality of Ar1001 are identical to or different from each other.)

[0571] In one embodiment, Ar 1001 is an aryl group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted.

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

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

[0574] In one embodiment, ax is 1.

[0575] Examples of the compound represented by the general formula (10) include the following compounds as specific examples.

[0576]

Chemical formula

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

[0578]

Chemical formula

[0579] (In the general formula (63a), R 631 combines with R 646 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. R 633 combines with R 647 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. R 634 combines with R 651 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. R 641 combines with R 642 to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. R 631 ~R 651 Among two or more adjacent ones of combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted fused ring, or do not combine with each other, do not form the substituted or unsubstituted heterocyclic ring, do not form the monocyclic ring, and do not form the fused ring, and R 631 ~R 651 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that R which does not form the substituted or unsubstituted heterocyclic ring, does not form the monocyclic ring, and does not form the condensed ring 631 ~R 651 at least one of which is a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.)

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

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

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

[0583] In one embodiment, the compound represented by 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 is selected from the group consisting of compounds represented by the following general formula (467).

[0584]

Chem.

[0585]

Chem.

[0586]

Chem.

[0587]

Chem.

[0588]

Chem.

[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 sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 437 、R 438 、and R that do not form the monocyclic ring and do not form the condensed ring 421 ~R 427 、R 431 ~R 436 、R 440 ~R 448 and R 451 ~R 454 are each independently a hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, X4 is an oxygen atom, NR 801 , or C(R 802 )(R 803 ), R 801 , R 802 and R 803 are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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-forming carbon atoms, R 801 When there are a plurality of R 801 are the same as or different from each other, R 802 When there are a plurality of R's, the plurality of R's 802 are the same as or different from each other, R 803 When there are a plurality of R's, the plurality of R's 803 are the same as or different from each other.)

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

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

Chemical formula

[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 are synonymous. )

[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]

Chemical formula

[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 and are synonymous, provided that R 421 ~R 427 and R 440 ~R 446 at least one of is a group represented by -N(R 906 )(R 907 ). )

[0598] In one embodiment, in the general formula (41-3-2), any two of R 421 ~R 427 and R 440 ~R 446 are groups represented by -N(R 906 )(R 907 ).

[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]

Chemical formula

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

Chemical formula

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

[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-forming 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 are hydrogen atoms.

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

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

[0610] In this specification, the "host material" is, for example, a material contained in "50% by mass or more of the layer". Therefore, for example, in the case of the organic EL element 1A, the light-emitting layer 5 contains the compound represented by the 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 film thickness of the light-emitting layer 5 is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the film thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and easy to adjust the chromaticity. When the film thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the increase in driving voltage.

[0612] (Content ratio of the compound 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 content ratios of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 are preferably in the following ranges, respectively. The content ratio 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 ratio of the light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content ratio 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 kind of the compound according to the first embodiment, or may contain two or more kinds. The light-emitting layer 5 may contain only one kind of the light-emitting compound, or may contain two or more kinds.

[0614] FIG. 2 shows a schematic configuration of another example of the organic EL element according to this embodiment. The organic EL element 1B shown in FIG. 2 is different from the organic EL element 1A in that the organic layer 10B includes the first light-emitting region 5B, and the other points are the same as those of the organic EL element 1A. The first light-emitting region 5B includes a first light-emitting layer 51 and a second light-emitting layer 52 in order from the anode 3 side. The first light-emitting layer 51 contains a first compound, and the second light-emitting layer 52 contains a second compound.

[0615] (The first compound) In the organic EL element 1B, the first compound is a compound according to the first embodiment. In the organic EL element according to the present 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] (The second compound) In the organic EL element 1B, the second compound is a compound represented by the following general formula (2).

[0617] [Chemical formula]

[0618] (In the general formula (2), R 201 ~R 208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, 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 a halogen atom a cyano group a nitro group a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and L 201 and L 202 each independently is a single bond a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, and Ar 201 and Ar 202 each independently is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming 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 each independently is a hydrogen atom a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and R 901 when there are a plurality of R 901 are the same as or different from each other, R 902When there are a plurality of them, the plurality of Rs 902 are the same as or different from each other, R 903 When there are a plurality of them, the plurality of Rs 903 are the same as or different from each other, R 904 When there are a plurality of them, the plurality of Rs 904 are the same as or different from each other, R 905 When there are a plurality of them, the plurality of Rs 905 are the same as or different from each other, R 906 When there are a plurality of them, the plurality of Rs 906 are the same as or different from each other, R 907 When there are a plurality of them, the plurality of Rs 907 are the same as or different from each other, R 801 When there are a plurality of them, the plurality of Rs 801 are the same as or different from each other, R 802 When there are a plurality of them, the plurality of Rs 802 are the same as or different from each other.)

[0620] In the organic EL element according to this embodiment, R 201 ~R 208 are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R905 a group represented by -N(R 906 )(R 907 ) 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 a halogen atom, a cyano group, or a nitro group, L 201 and L 202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, Ar 201 and Ar 202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, preferably.

[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-forming carbon atoms, Ar 201 and Ar 202 are each independently preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

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

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

[0624]

Chem.

[0625]

Chem.

[0626]

Chem.

[0627]

Chem.

[0628]

Chem.

[0629]

Chem.

[0630] [Chemical formula]

[0631] [Chemical formula]

[0632] [Chemical formula]

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

[0634] It is also preferable that the second compound represented by the general formula (2) is 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] [Chemical formula]

[0636] [Chemical formula]

[0637] [Chemical formula]

[0638]

Chem.

[0639]

Chem.

[0640]

Chem.

[0641]

Chem.

[0642]

Chem.

[0643]

Chem.

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

[0645] It is also preferable that the second compound represented by the general formula (2) is 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]

Chemical formula

[0647]

Chemical formula

[0648]

Chemical formula

[0649]

Chemical formula

[0650]

Chemical formula

[0651]

Chemical formula

[0652]

Chemical formula

[0653] [Chem.]

[0654] [Chem.]

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

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

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

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

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

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

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

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

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

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

[0665]

Chemical formula

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

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

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

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

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

[0671] (Specific examples of the second compound) Specific examples of the second compound include, for example, the following compounds. However, the present invention is not limited to these specific examples of the second compound.

[0672]

Chemical formula

[0673]

Chemical formula

[0674]

Chemical formula

[0675]

Chemical formula

[0676]

Chemical formula

[0677] [Chemistry]

[0678] [Chemistry]

[0679] [Chemistry]

[0680] [Chemistry]

[0681] [Chemistry]

[0682] [Chemistry]

[0683] [Chemistry]

[0684] [Chemistry]

[0685] [Chemistry]

[0686] [Chemistry]

[0687] [Chemistry]

[0688]

Chem.

[0689]

Chem.

[0690]

Chem.

[0691]

Chem.

[0692]

Chem.

[0693]

Chem.

[0694]

Chem.

[0695]

Chem.

[0696]

Chem.

[0697]

Chem.

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

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

[0700] In one embodiment, when the substituent in the case of "substituted or unsubstituted" in each formula 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-forming carbon atoms, -Si(R 901a )(R 902a )(R 903a ) group represented by -O-(R 904a ) group represented by -S-(R 905a ) group represented by -N(R 906a )(R 907aa group represented by a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901a ~R 907a each independently is a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901a when two or more Rs are present, the two or more Rs 901a are the same as or different from each other, R 902a when two or more Rs are present, the two or more Rs 902a are the same as or different from each other, R 903a when two or more Rs are present, the two or more Rs 903a are the same as or different from each other, R 904a when two or more Rs are present, the two or more Rs 904a are the same as or different from each other, R 905a when two or more Rs are present, the two or more Rs 905a are the same as or different from each other, R 906a when two or more Rs are present, the two or more Rs 906a are the same as or different from each other, R 907a when two or more Rs are present, the two or more Rs 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-forming carbon atoms, or It is a heterocyclic group having 5 to 50 ring-forming atoms without substitution.

[0702] In one embodiment, when 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-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring-forming 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 exhibits light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits light emission with a maximum peak wavelength 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 light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescent light emission with a maximum peak wavelength 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 exhibits light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits light emission 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 light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescent light emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.

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

[0706] In the organic EL element 1B, 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 (Formula 1). T1(H1)>T1(H2) …(Formula 1)

[0707] Conventionally, as a technique for improving the light emission efficiency of an organic EL element, Triplet-Triplet-Annihilation (sometimes referred to as TTA) is known. TTA is a mechanism in which triplet excitons collide to generate singlet excitons. Note that the TTA mechanism may also be referred to as the TTF mechanism as described in International Publication No. 2010 / 134350.

[0708] Explain the TTF phenomenon. The holes injected from the anode and the electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As is conventionally known, the spin state is such that the singlet excitons are 25% and the triplet excitons are 75%. In a conventionally known fluorescent element, light is emitted when 25% of the singlet excitons relax to the ground state, but for the remaining 75% of the triplet excitons, they return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit value of the internal quantum efficiency of a conventional fluorescent element has been said to be 25%. On the other hand, the behavior of triplet excitons generated inside an organic substance 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, when the density of triplet excitons (hereinafter, 3 A * as described) increases, triplet excitons collide with each other and a reaction as shown in the following formula occurs. Here, 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 out of the initially generated 75% triplet excitons, 1 / 5, that is, 20%, will change into singlet excitons. Therefore, the singlet excitons contributing as light are 40% obtained by adding 75%×(1 / 5)=15% to the initially generated 25%. At this time, the emission ratio (TTF ratio) of the emission derived from TTF in the total emission intensity is 15 / 40, that is, 37.5%. Also, assuming that the initially generated 75% triplet excitons collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), a very high internal quantum efficiency of 62.5% is obtained by adding 75%×(1 / 2)=37.5% to the initially generated 25% singlet excitons. At this time, the TTF ratio is 37.5 / 62.5 = 60%.

[0709] According to the organic EL element according to this embodiment, even if carriers are present in excess at the interface between the first light-emitting layer and the organic layer directly in contact with the first light-emitting layer, the triplet excitons present at the interface between the first light-emitting layer and the organic layer are considered to be difficult to be quenched. 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 barrier layer, quenching by excess electrons is considered. 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 barrier layer, quenching by excess holes is considered. The organic EL element 1B includes at least two light-emitting layers (i.e., the first light-emitting layer 51 and the second light-emitting layer 52) that satisfy a predetermined relationship. By providing the first light-emitting layer 51 and the second light-emitting layer 52 such that the triplet energy T1(H1) of the first compound in the first light-emitting layer 51 and the triplet energy T1(H2) of the second compound in the second light-emitting layer 52 satisfy the relationship of the formula (Equation 1), the triplet excitons generated in the first light-emitting layer 51 can move to the second light-emitting layer without being quenched by excess carriers, and the reverse movement from the second light-emitting layer 52 to the first light-emitting layer 51 can be suppressed. As a result, in the second light-emitting layer 52, the TTF mechanism is manifested, singlet excitons are efficiently generated, and the luminous efficiency is improved. In this way, the organic EL element 1B includes, as different regions, a first light-emitting layer 51 that mainly generates triplet excitons and a second light-emitting layer 52 that mainly manifests the TTF mechanism by utilizing the triplet excitons that have moved from the first light-emitting layer 51. By using a compound having a smaller triplet energy than the first compound in the first light-emitting layer as the second compound in the second light-emitting layer and providing a difference in triplet energy, the luminous efficiency is improved.

[0710] (Triplet energy T1) Examples of the method for measuring the triplet energy T1 include the following method. A compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 -5 mol / L or more and 10 -4 mol / L or less to prepare a solution. This solution is placed in a quartz cell to obtain a measurement sample. For this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]). A tangent is drawn to the rising edge on the short-wavelength side of this phosphorescence spectrum, and the energy amount calculated from the following conversion formula (F1) based on the wavelength value λ edge [nm] of the intersection of the tangent and the horizontal axis is defined as the triplet energy T1. Conversion formula (F1): T1 [eV] = 1239.85 / λ edge

[0711] Draw a tangent to the rising edge on the short-wavelength side of the phosphorescence spectrum as follows. When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the maximum value of the spectrum that is the shortest in wavelength among the maximum values of the spectrum, consider the tangents at each point on the curve toward the long-wavelength side. As the curve rises (i.e., as the vertical axis increases), the slope of this tangent increases. The tangent drawn at the point where the value of this slope reaches a maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge on the short-wavelength side of the phosphorescent spectrum. Note that the maximum points having a peak intensity of 15% or less of the maximum peak intensity of the spectrum are not included in the above-mentioned maximum value that is the shortest in wavelength, and the tangent drawn at the point closest to the maximum value that is the shortest in wavelength and where the value of the slope reaches a maximum is the tangent to the rising edge on the short-wavelength side of the phosphorescent spectrum. For the measurement of phosphorescence, an F-4500 type spectrofluorophotometer main body manufactured by Hitachi High-Technologies Corporation can be used. Note that the measuring device is not limited to this, and it may be measured 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 following formula (Formula 2). S1(H1)>S1(D3)…(Formula 2)

[0713] (Singlet energy S1) Examples of the measurement method of the singlet energy S1 using a solution (which may be referred to as the solution method) include the following method. 10 of the compound to be measured -5 mol / L or more and 10 -4Prepare a toluene solution with a concentration of 1 mol / L or less, put it into a quartz cell, and measure the absorption spectrum of this sample at room temperature (300 K) (the vertical axis: absorption intensity, the horizontal axis: wavelength). Draw a tangent to the downward slope on the long-wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of this tangent and the horizontal axis into the following conversion formula (F2) to calculate the singlet energy S1. Conversion formula (F2): S1 [eV] = 1239.85 / λedge Examples of the absorption spectrum measuring device include, but are not limited to, the spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd.

[0714] The tangent to the downward slope on the long-wavelength side of the absorption spectrum is drawn as follows. Among the maximum values of the absorption spectrum, when moving along the spectrum curve in the long-wavelength direction from the maximum value on the longest-wavelength side, consider the tangent at each point on the curve. This tangent repeats the process that as the curve slopes downward (that is, as the value on the vertical axis decreases), the slope decreases and then increases. The tangent drawn at the point where the value of the slope takes the minimum value on the longest-wavelength side (however, excluding the case where the absorbance is 0.1 or less) is defined as the tangent to the downward slope on the long-wavelength side of the absorption spectrum. Note that the maximum points with an absorbance value of 0.2 or less are not included in the maximum value on the longest-wavelength side described above.

[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)… (mathematical formula 3)

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

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

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

[0720] Note that this embodiment does not exclude the case where materials other than the first compound and the first light-emitting compound are included in the first light-emitting layer 51. The first light-emitting layer 51 may contain only one type of the first compound or may contain two or more types of the first compound. The first light-emitting layer 51 may contain only one type of the first light-emitting compound or may contain two or more types of the first light-emitting compound.

[0721] When the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the content rates 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 rate 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 rate of the second light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content rate of the second compound and the second light-emitting compound in the second light-emitting layer 52 is 100% by mass.

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

[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 of "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) In the process of passing through the step of vapor-depositing the compound related to the first light-emitting layer 51 and the step of vapor-depositing the compound related to 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 occurs, and the region exists 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, in the process of passing through the step of vapor-depositing the compound related to the first light-emitting layer 51 and the step of vapor-depositing the compound related to the second light-emitting layer 52, a region in which the first host material, the second host material, and the light-emitting compound are mixed occurs, and the region exists 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, in the process of passing through the step of vapor-depositing the compound related to the first light-emitting layer 51 and the step of vapor-depositing the compound related to the second light-emitting layer 52, a region composed of the light-emitting compound, a region composed of the first host material, or a region composed of the second host material occurs, and the region exists 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 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 of "the second light-emitting layer 52 and the third light-emitting layer are in direct contact with each other" For example, it may also include any one of the following modes (LS4), (LS5), and (LS6). (LS4) In the process of passing through the step of vapor-depositing the compound related to the second light-emitting layer 52 and the step of vapor-depositing the compound related to the third light-emitting layer, a region in which both the second host material and the third host material (the host material contained in the third light-emitting layer) are mixed occurs, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer. When the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region where the second host material, the third host material, and the light-emitting compound are mixed occurs in the process of passing through the step of depositing the compound related to the second light-emitting layer 52 and the step of depositing the compound related to the third light-emitting layer, and the mode in which the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer. When the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region composed of the light-emitting compound, a region composed of the second host material, or a region composed of the third host material occurs in the process of passing through the step of depositing the compound related to the second light-emitting layer 52 and the step of depositing the compound related to the third light-emitting layer, and the mode in which the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

[0727] The organic EL element 1B preferably 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 intervening layer is preferably a non-doped layer. The intervening layer preferably does not contain metal atoms. The intervening layer contains an intervening layer material. The intervening layer material is preferably not a light-emitting compound. The intervening layer material is not particularly limited, but is preferably a material other than a light-emitting compound. Examples of the intervening layer material include 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, and 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

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

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

[0731] The intermediate layer may be composed of a single layer or may be composed of two or more layers stacked.

[0732] The film thickness of the intermediate 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 configuration of each layer common to the organic EL element 1A and the organic EL element 1B will be further described. Hereinafter, the description of symbols may be omitted.

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

[0735] (Anode) For the anode 3 formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, and mixtures thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. can be mentioned. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (for example, titanium nitride) etc. can be mentioned.

[0736] These materials are usually formed into a film by a sputtering method. For example, indium zinc oxide can be formed by a sputtering method using a target in which 1 mass% or more and 10 mass% or less of zinc oxide is added to indium oxide. Also, for example, tungsten oxide and indium oxide containing zinc oxide can be formed by a sputtering method using a target containing 0.5 mass% or more and 5 mass% or less of tungsten oxide and 0.1 mass% or more and 1 mass% or less of zinc oxide with respect to indium oxide. Alternatively, it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, etc.

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

[0738] Elements belonging to Group 1 or Group 2 of the periodic table, which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these can also be used. When forming the anode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste or the like, a coating method or an inkjet method can be used.

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

[0740] When forming the cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Also, when using a silver paste or the like, a coating method or an inkjet method can be used.

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

[0742] (Hole injection layer) The hole injection layer 61 is a layer containing a substance with high hole injection properties. As the substance with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0743] In addition, as substances with high hole injection properties, 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), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) and other aromatic amine compounds, and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) can also be mentioned.

[0744] In addition, as substances with high hole injection properties, high molecular weight compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, high molecular weight compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be mentioned. In addition, high molecular weight compounds added with acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), 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. In the hole transport layer 62, an aromatic amine compound, a carbazole derivative, an anthracene derivative, etc. 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: DFLDPBi), 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-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and other aromatic amine compounds can be used. The substances described here mainly have a hole mobility of 10 -6 cm 2 / (V·s) or more.

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

[0747] However, as long as it is a substance with higher hole transport properties than electrons, other substances may be used. Note that the layer containing a substance with high hole transport properties may be not only a single layer but also a layer formed by laminating two or more layers of the above substances.

[0748] (Electron transport layer) The electron transport layer 71 is a layer containing a substance with high electron transport properties. In the electron transport layer 71, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-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: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In this embodiment, a benzimidazole compound can be preferably used. The substances described here mainly have an electron mobility of 10 -6 cm 2 / (V·s) or more. As long as the substance has higher electron transport properties than hole transport properties, substances other than the above can also be used as the electron transport layer. Also, the electron transport layer may be composed of a single layer, or may be composed of two or more layers of the above substances laminated.

[0749] In addition, a polymer compound can also be used for the electron transport layer 71. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. 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, or their compounds such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), etc. can be used. In addition, substances obtained by incorporating alkali metals, alkaline earth metals, or their compounds into an electron transporting substance, specifically, those obtained by incorporating magnesium (Mg) into Alq, etc. may also be used. In this case, electron injection from the cathode can be performed more efficiently.

[0751] Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used for the electron injection layer 72. Since such a composite material generates electrons in the organic compound by the electron donor, it is excellent in electron injection properties and electron transport properties. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, the substances constituting the above-described electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. Any substance that exhibits electron donating properties with respect to the organic compound can be used as the electron donor. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0752] (Layer formation method) As the method for forming each layer of the organic EL element of the present embodiment, it is not limited except as specifically mentioned above. Known methods such as dry film formation methods such as vacuum evaporation method, sputtering method, plasma method, ion plating method, etc., and wet film formation methods such as spin coating method, dipping method, flow coating method, inkjet method, etc. can be adopted.

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

[0754] According to the present embodiment, an organic electroluminescence element with improved lifespan can be provided.

[0755] 〔Third Embodiment〕 (Electronic device) The electronic device according to the present embodiment is equipped with any one of the organic EL elements 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 a display component (for example, an organic EL panel module, etc.), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lamps.

[0756] 〔Modification of the Embodiment〕 Note that the present invention is not limited to the above-described embodiments, and changes, improvements, etc. within the scope that can achieve the object of the present invention are included in the present invention.

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

[0758] Also, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The barrier layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a barrier layer is disposed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching a layer on the cathode side of the barrier layer (for example, an electron transport layer). When the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer. Also, when a barrier layer is disposed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching a layer on the anode side of the barrier layer (for example, a hole transport layer). When the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light-emitting layer and the hole transport layer. Also, a barrier layer may be provided adjacent to the light-emitting layer so that excitation energy does not leak from the light-emitting layer to its peripheral layer. This prevents excitons generated in the light-emitting layer from moving to a layer on the electrode side of the barrier layer (for example, an electron transport layer and a hole transport layer, etc.). The light-emitting layer and the barrier layer are preferably joined.

[0759] In addition, specific structures, shapes, etc. in the implementation of the present invention may be other structures, etc. within the range that can achieve the object of the present invention.

Examples

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

[0761]

Chemical formula

[0762]

Chemical formula

[0763]

Chemical formula

[0764]

Chemical formula

[0765]

Chemical formula

[0766]

Chemical formula

[0767]

Chemical formula

[0768]

Chemical formula

[0769] The structure of the comparative compound used in the production of the organic EL element according to the comparative example is shown below.

[0770]

Chem.

[0771]

Chem.

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

[0773]

Chem.

[0774]

Chem.

[0775]

Chem.

[0776] <Fabrication of Organic EL Element (1)> Organic EL elements were fabricated and evaluated as follows.

[0777] 〔Example 1〕 A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The glass substrate with the cleaned transparent electrode line was mounted on the substrate holder of a vacuum evaporation apparatus, and first, Compound HIL-1 was evaporated so as to cover the transparent electrode on the surface where the transparent electrode line was formed, and a hole injection layer (HI) with a film thickness of 5 nm was formed. Following the film formation of the hole injection layer, Compound HTL-1 was evaporated to form a first hole transport layer with a film thickness of 80 nm. Following the formation of the first hole transport layer, Compound EBL-1 was vapor-deposited to form a second hole transport layer (also referred to as an electron blocking layer) with a film thickness of 10 nm. On the second hole transport layer, Compound BH1-1 as the first compound and Compound BD-1 as the first light-emitting compound were co-vapor-deposited such that the proportion of Compound BD-1 was 2% by mass to form a first light-emitting layer with a film thickness of 12.5 nm. On the first light-emitting layer, Compound BH-2 as the second compound and Compound BD-1 as the second light-emitting compound were co-vapor-deposited such that the proportion of Compound BD-1 was 2% by mass to form a second light-emitting layer with a film thickness of 12.5 nm. Compound aET-1 was vapor-deposited on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) with a film thickness of 10 nm. Compound bET-1 was vapor-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. LiF was vapor-deposited on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm. Metal Al was vapor-deposited on the electron injection layer to form a cathode with a film thickness of 80 nm. The device structure of Example 1 is schematically shown as follows. ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-1:BD-1(12.5,98%:2%) / BH-2:BD-1(12.5,98%:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the parentheses, the percentage numbers (98%:2%) indicate the proportion (by mass) of Compound BH1-1 or Compound BH-2 and Compound BD-1 in the first light-emitting layer or the second light-emitting layer.

[0778] 〔Example 2〕 The organic EL device of Example 2 was fabricated in the same manner as Example 1, except that the first compound in the first light-emitting layer was changed to the compound described in Table 1.

[0779] 〔Comparative Examples 1, 2, and 3〕 The organic EL elements of Comparative Examples 1, 2, and 3 were each fabricated in the same manner as in Example 1, except that the first compound in the first light-emitting layer was changed to the compounds described in Table 1.

[0780] <Evaluation of Organic EL Element (1)> The following evaluations were performed on the organic EL elements fabricated in Examples 1 and 2 and Comparative Examples 1, 2, and 3. The evaluation results are shown in Table 1.

[0781] · Lifetime (LT95) A voltage was applied to the obtained organic EL element so that the current density was 50 mA / cm 2 and the time (LT95 (unit: hours)) until the luminance became 95% of the initial luminance was measured. The luminance was measured using a spectro-radiance meter CS-2000 (manufactured by Konica Minolta, Inc.).

[0782]

Table 1

[0783] <Fabrication of Organic EL Element (2)> The organic EL element was fabricated and evaluated as follows.

[0784] 〔Example 3〕 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) having a size of 25 mm × 75 mm × 1.1 mm thick was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV-ozone cleaned for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with the transparent electrode line was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound HTL-2 and Compound HIL-2 were co-evaporated so as to cover the transparent electrode on the surface where the transparent electrode line was formed, and a hole injection layer with a film thickness of 10 nm was formed. The ratio of Compound HTL-2 in this hole injection layer was 90% by mass, and the ratio of Compound HIL-2 was 10% by mass. Following the formation of the hole injection layer, Compound HTL-2 was evaporated to form a first hole transport layer with a film thickness of 85 nm. Following the formation of the first hole transport layer, Compound EBL-2 was vapor-deposited to form a second hole transport layer (also referred to as an electron blocking layer) with a film thickness of 5 nm. On the second hole transport layer, Compound BH1-1 as the first compound and Compound BD-2 as the first light-emitting compound were co-vapor-deposited such that the proportion of Compound BD-2 was 2% by mass to form a first light-emitting layer with a film thickness of 10 nm. On the first light-emitting layer, Compound BH-3 as the second compound and Compound BD-2 as the second light-emitting compound were co-vapor-deposited such that the proportion of Compound BD-2 was 2% by mass to form a second light-emitting layer with a film thickness of 10 nm. Compound aET-2 was vapor-deposited on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) with a film thickness of 5 nm. Compound bET-2 and Compound Liq were co-vapor-deposited on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The proportion of Compound bET-2 in this second electron transport layer was 50% by mass, and the proportion of Compound Liq was 50% by mass. Note that Liq is an abbreviation for (8-Quinolinolato)lithium. Compound Liq was vapor-deposited on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm. Metal Al was vapor-deposited on the electron injection layer to form a cathode with a film thickness of 80 nm. The device structure of Example 3 is schematically shown as follows. ITO(130) / HTL-2:HIL-2(10, 90%:10%) / HTL-2(85) / EBL-2(5) / BH1-1:BD-2(10, 98%:2%) / BH-3:BD-2(10, 98%:2%) / aET-2(5) / bET-2:Liq(25, 50%:50%) / Liq(1) / Al(80) Note that the numbers in parentheses indicate the film thickness (unit: nm). Similarly, within the parentheses, the percentages (90%:10%) represent the ratios (mass %) of compound HTL-2 and compound HIL-2 in the hole injection layer, the percentages (98%:2%) represent the ratios (mass %) of BH1-1 or BH-3 and compound BD-2 in the first light-emitting layer or the second light-emitting layer, and the percentages (50%:50%) represent the ratios (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 elements of Examples 4, 5, 6, 7, 8, 9, 10, 11, and 12 were each fabricated in the same manner as in Example 3, except that the first compound in the first light-emitting layer was changed to the compound described in Table 2.

[0786] <Evaluation of Organic EL Element (2)> The organic EL elements fabricated 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] · Lifetime (LT95) A voltage was applied to the obtained organic EL element such that the current density became 50 mA / cm 2 and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The luminance was measured using a spectro-radiance meter CS-2000 (manufactured by Konica Minolta, Inc.).

[0788]

Table 2

[0789] <Fabrication of Organic EL Element (3)> The organic EL element was fabricated and evaluated as follows.

[0790] 〔Example 13〕 A glass substrate (manufactured by Geomatic Co., Ltd.) with a 25 mm × 75 mm × 1.1 mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The glass substrate with the transparent electrode line after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HIL-1 was evaporated so as to cover the transparent electrode on the surface where the transparent electrode line was formed, and a hole injection layer (HI) with a film thickness of 5 nm was formed. Following the film formation of the hole injection layer, compound HTL-1 was evaporated to form a first hole transport layer with a film thickness of 80 nm. Following the film 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 barrier layer) with a film thickness of 10 nm. Compound BH1-7 as the first compound and compound BD-1 as the first light-emitting compound were co-evaporated on the second hole transport layer such that the ratio of compound BD-1 was 2% by mass to form a first light-emitting layer with a film thickness of 12.5 nm. Compound BH-2 as the second compound and compound BD-1 as the second light-emitting compound were co-evaporated on the first light-emitting layer such that the ratio of compound BD-1 was 2% by mass to form a second light-emitting layer with a film thickness of 12.5 nm. Compound aET-1 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole barrier layer) with a film thickness of 10 nm. Compound bET-1 was evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 15 nm. LiF was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm. Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm. The element configuration of Example 13 is schematically shown as follows. ITO(130) / HIL-1(5) / HTL-1(80) / EBL-1(10) / BH1-7:BD-1(12.5,98%:2%) / BH-2:BD-1(12.5,98%:2%) / aET-1(10) / bET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the percentages (98%: 2%) indicate the ratios (mass%) of compound BH1-7 or compound BH-2 and compound BD-1 in the first light-emitting layer or the second light-emitting layer.

[0791] [Examples 14, 15, 16, 17, 18, 19, and 20] The organic EL elements 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 light-emitting layer was changed to the compound described in Table 3.

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

[0793] [Evaluation of Organic EL Element (3)] The following evaluations were performed on the organic EL elements fabricated in Examples 13, 14, 15, 16, 17, 18, 19, and 20, and Comparative Example 4. The evaluation results are shown in Table 3.

[0794] ·CIE1931 Chromaticity The CIE1931 chromaticity coordinates (x, y) were measured with a spectro-radiance meter CS-2000 (manufactured by Konica Minolta Inc.) when a voltage was applied to the element so that the current density became 10.00 mA / cm 2

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

[0796]

Table 3

[0797] <Fabrication of Organic EL Element (4)> The organic EL element was fabricated and evaluated as follows.

[0798] 〔Example 21〕 A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) having a size of 25 mm × 75 mm × 1.1 mm thick was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm. The cleaned glass substrate with the transparent electrode line was mounted on the substrate holder of a vacuum evaporation apparatus. First, the compound HTL-2 and the compound HIL-2 were co-evaporated so as to cover the transparent electrode on the surface where the transparent electrode line was formed, and a hole injection layer with a film thickness of 10 nm was formed. The ratio of the compound HTL-2 in this hole injection layer was 90% by mass, and the ratio of the compound HIL-2 was 10% by mass. Following the formation of the hole injection layer, the compound HTL-2 was evaporated to form a first hole transport layer with a film thickness of 85 nm. Following the formation of the first hole transport layer, the compound EBL-2 was evaporated to form a second hole transport layer (also referred to as an electron barrier layer) with a film thickness of 5 nm. On the second hole transport layer, the compound BH1-7 as the first compound and the compound BD-3 as the first light-emitting compound were co-evaporated so that the ratio of the compound BD-3 was 2% by mass, and a first light-emitting layer with a film thickness of 10 nm was formed. Compound BH-3 as the second compound and compound BD-3 as the second light-emitting compound were co-evaporated on the first light-emitting layer such that the proportion of compound BD-3 was 2% by mass to form a second light-emitting layer with a film thickness of 10 nm. Compound aET-2 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole barrier layer) with a film thickness of 5 nm. Compound bET-2 and compound Liq were co-evaporated on the first electron transport layer to form a second electron transport layer with a film thickness of 25 nm. The proportion of compound bET-2 in this second electron transport layer was 50% by mass, and the proportion of compound Liq was 50% by mass. Compound Liq was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm. Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm. The device structure of Example 21 is schematically shown as follows. ITO(130) / HTL-2:HIL-2(10, 90%:10%) / HTL-2(85) / EBL-2(5) / BH1-7:BD-3(10, 98%:2%) / BH-3:BD-3(10, 98%:2%) / aET-2(5) / bET-2:Liq(25, 50%:50%) / Liq(1) / Al(80) Note that the numbers in parentheses indicate the film thickness (unit: nm). Also in parentheses, the percent-displayed numbers (90%:10%) indicate the proportions (by mass) of compound HTL-2 and compound HIL-2 in the hole injection layer, the percent-displayed numbers (98%:2%) indicate the proportions (by mass) of BH1-7 or BH-3 and compound BD-3 in the first light-emitting layer or the second light-emitting layer, and the percent-displayed numbers (50%:50%) indicate the proportions (by 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 fabricated in the same manner as Example 21, except that the first compound in the first light-emitting layer was changed to the compound described in Table 4.

[0800] 〔Comparative Example 5〕 The organic EL element of Comparative Example 5 was fabricated in the same manner as in Example 21, except that the first compound in the first light-emitting layer was changed to the compound described in Table 4.

[0801] <Evaluation of Organic EL Element (4)> The following evaluations were performed on the organic EL elements fabricated in Examples 21 and 22 and Comparative Example 5. The evaluation results are shown in Table 4.

[0802] ·CIE1931 Chromaticity The CIE1931 chromaticity coordinates (x, y) were measured with a spectro-radiance meter CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the element so that the current density became 10.00 mA / cm 2 .

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

[0804]

Table 4

[0805] <Fabrication of Organic EL Element (5)> Organic EL elements were fabricated and evaluated as follows.

[0806] 〔Examples 23, 24, and 25〕 The organic EL elements of Examples 23, 24, and 25 were fabricated in the same manner as in Example 1, except that the first compound in the first light-emitting layer was changed to the compound described in Table 5, respectively.

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

[0808] [Evaluation of Organic EL Element (5)] The following evaluations were performed on the organic EL elements fabricated in Examples 23, 24, and 25, and Comparative Example 6. The evaluation results are shown in Table 5.

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

[0810] [Table 5]

[0811] [Fabrication of Organic EL Element (6)] The organic EL element was fabricated and evaluated as follows.

[0812] [Example 26] The organic EL element of Example 26 was fabricated in the same manner as in Example 3, except that the first compound in the first light-emitting layer was changed to the compound described in Table 6.

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

[0814] <Evaluation of Organic EL Element (6)> For the organic EL elements fabricated in Example 26 and Comparative Example 7, the following evaluations were conducted. The evaluation results are shown in Table 6.

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

[0816]

Table 6

[0817] <Fabrication of Organic EL Element (7)> Organic EL elements were fabricated and evaluated as follows.

[0818] 〔Example 27〕 The organic EL element of Example 27 was fabricated in the same manner as in Example 21, except that the first compound in the first light-emitting layer was changed to the compound described in Table 7.

[0819] 〔Comparative Example 8〕 The organic EL element of Comparative Example 8 was fabricated in the same manner as in Example 21, except that the first compound in the first light-emitting layer was changed to the compound described in Table 7.

[0820] <Evaluation of Organic EL Element (7)> For the organic EL elements fabricated in Example 27 and Comparative Example 8, the following evaluations were conducted. The evaluation results are shown in Table 7.

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

[0822]

Table 7

[0823] <Evaluation of Compounds> (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 obtain a measurement sample. For this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) was measured at low temperature (77 [K]). A tangent was drawn to the rising edge on the short-wavelength side of this phosphorescence spectrum, and the energy amount calculated from the following conversion formula (F1) based on the wavelength value λ edge [nm] of the intersection of the tangent and the horizontal axis was defined as the triplet energy T1. The results are as shown in Table 1 and Table 2. Note that 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 on the short-wavelength side of the phosphorescence spectrum is drawn as follows. When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the maximum value on the shortest-wavelength side among the maximum values of the spectrum, the tangents at each point on the curve are considered in the long-wavelength direction. As the curve rises (i.e., as the vertical axis increases), the slope of this tangent increases. The tangent drawn at the point where the value of this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge on the short-wavelength side of the corresponding phosphorescence spectrum. Note that the maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the maximum value on the shortest-wavelength side described above. The tangent drawn at the point closest to the maximum va...

Claims

1. A compound represented by the following general formula (1A). 【Chemical Formula 1】 (In the general formula (1A), R11 is a group represented by the general formula (1B), R １ ~ R １０ and R １２ are each independently a hydrogen atom, In the general formula (1B), n1 is 0, Ar １ is a substituted or unsubstituted benzonaphthofuranyl group, * indicates the bonding position with the benz[a]anthracene ring in the general formula (1A), provided that at least one of R １ ~ R １２ in the general formula (1A) is a deuterium atom.)

2. In the compound according to Claim 1, R １ ~ R １０ and R １２ are all deuterium atoms, a compound.

3. In the compound according to Claim 1, Ar １ is a group represented by the following general formula (1B-1), (1B-2), or (1B-3), a compound. 【Chemical Formula 2】 (In the groups represented by the general formula (1B-1), (1B-2), and (1B-3), n1 is 0, In the general formula (1B-1), R ５１ ~ R ５４ R ５７ and R ６１ ~ R ６４At least one set consisting of two or more adjacent ones among them, combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring, and R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a group represented by -Si(R ９０１ )(R ９０２ )(R ９０３ ), a group represented by -O-(R ９０４ ), a group represented by -S-(R ９０５ ), a group represented by -N(R ９０６ )(R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, * indicates the bonding position with 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 ７４At least one set of two or more adjacent ones among them, combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, R ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ are each independently the same as R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ in the general formula (1B-1), * indicates the bonding position with 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 At least one set of two or more adjacent ones among them, combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, R ５１ ~R ５５ , and R ８１ ~R ８４ are each independently the same as R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ in the general formula (1B-1), * indicates the bonding position with the benz[a]anthracene ring in the general formula (1A), In the groups represented by the general formulas (1B-1), (1B-2), and (1B-3), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , and R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, When there are a plurality of R ９０１ , the plurality of R ９０１ are the same as or different from each other, When there are a plurality of R ９０２ , the plurality of R ９０２ are the same as or different from each other, When there are a plurality of R ９０３ , the plurality of R ９０３ are the same as or different from each other, When there are a plurality of R ９０４ , the plurality of R ９０４ are the same as or different from each other, When there are a plurality of R ９０５ , the plurality of R ９０５ are the same as or different from each other, When there are a plurality of R ９０６ , the plurality of R ９０６ are the same as or different from each other, When there are a plurality of R ９０７ , the plurality of R ９０７ are the same as or different from each other. )

4. In the compound according to claim 1, 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, Compound.

5. An organic electroluminescence device containing the compound according to any one of Claims 1 to 4, organic electroluminescence device.

6. The organic electroluminescence device according to Claim 5, an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one layer of the organic layer contains the compound, organic electroluminescence device.

7. The organic electroluminescence device according to Claim 6, 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 electroluminescence device.

8. an anode, a cathode, and 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 electroluminescence device. 【Chemical Formula 3】 (In the general formula (100A), R111 is a group represented by the general formula (100B), R １０１ ~ R １１０ and R １１２ are each independently, a hydrogen atom, In the general formula (100B), n101 is 0, Ar １０１ is a substituted or unsubstituted benzonaftfuranyl group, * indicates the bonding position to the benz[a]anthracene ring in the general formula (100A), provided that at least one of R １０１ to R １１２ among them is a deuterium atom. )

9. In the organic electroluminescence element according to Claim 8, the triplet energy T １ (H1) of the first compound and the triplet energy T １ (H2) of the second compound satisfy the following relational expression (Equation 1), organic electroluminescence element. T １ (H1) > T １ (H2)... (Equation 1)

10. In the organic electroluminescence element according to Claim 8, R １０１ to R １１０ and R １１２ are both deuterium atoms, organic electroluminescence element.

11. In the organic electroluminescence element according to Claim 8, Ar １０１ is a group represented by the following general formula (1B-1), (1B-2), or (1B-3), organic electroluminescence element. [Chemical Formula 4] (In the groups represented by the general formula (1B-1), (1B-2), and (1B-3), n1 is 0, in the general formula (1B-1), R ５１ to R ５４ and R ５７ and R ６１ ~R ６４ One or more sets of two or more adjacent ones among them are combined with each other to form a substituted or unsubstituted monocyclic ring, combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a group represented by -Si(R ９０１ )(R ９０２ )(R ９０３ ), a group represented by -O-(R ９０４ ), a group represented by -S-(R ９０５ ), a group represented by -N(R ９０６ )(R ９０７ ), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, * indicates the bonding position with the benz[a]anthracene ring in the general formula (100A), In the general formula (1B-2), R ５１ ~R ５３ , R ５６ , R ５７ , and R ７１~R ７４ At least one set of two or more adjacent ones among them is joined to each other to form a substituted or unsubstituted monocyclic ring, joined to each other to form a substituted or unsubstituted condensed ring, or not joined to each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, R ５１ ~R ５３ , R ５６ , R ５７ , and R ７１ ~R ７４ are each independently the same as R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ in the general formula (1B - 1), * indicates the bonding position with the benz[a]anthracene ring in the general formula (100A), In the general formula (1B - 3), R ５１ ~R ５５ , and R ８１ ~R ８４ At least one set of two or more adjacent ones among them is joined to each other to form a substituted or unsubstituted monocyclic ring, joined to each other to form a substituted or unsubstituted condensed ring, or not joined to each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, R ５１ ~R ５５ , and R ８１ ~R ８４ are each independently the same as R ５１ ~R ５４ , R ５７ , and R ６１ ~R ６４ in the general formula (1B - 1), * indicates the bonding position with the benz[a]anthracene ring in the general formula (100A), In the groups represented by the general formulas (1B-1), (1B-2), and (1B-3), R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , and R ９０７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, When there are a plurality of R ９０１ , the plurality of R ９０１ are the same as or different from each other, When there are a plurality of R ９０２ , the plurality of R ９０２ are the same as or different from each other, When there are a plurality of R ９０３ , the plurality of R ９０３ are the same as or different from each other, When there are a plurality of R ９０４ , the plurality of R ９０４ are the same as or different from each other, When there are a plurality of R ９０５ , the plurality of R ９０５ are the same as or different from each other, When there are a plurality of R ９０６ , the plurality of R ９０６ are the same as or different from each other, When there are a plurality of R ９０７ , the plurality of R ９０７ are the same as or different from each other. )

12. In the organic electroluminescence element according to claim 8, all of the groups described as "substituted or unsubstituted" are "unsubstituted" groups, All of the rings described as "substituted or unsubstituted" are "unsubstituted" rings. Organic electroluminescence device.

13. In the organic electroluminescence device according to claim 8, the first light-emitting layer and the second light-emitting layer are in direct contact with each other. Organic electroluminescence device.

14. In the organic electroluminescence device according to claim 8, the first light-emitting layer is disposed between the anode and the second light-emitting layer. Organic electroluminescence device.

15. In the organic electroluminescence device according to claim 8, 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 light-emitting compound and the second light-emitting compound are each independently a compound that exhibits light emission with a maximum peak wavelength of 500 nm or less. Organic electroluminescence device.

16. In the organic electroluminescence device according to claim 8, a hole transport layer is provided between the anode and the light-emitting region. Organic electroluminescence device.

17. In the organic electroluminescence device according to claim 8, an electron transport layer is provided between the cathode and the light-emitting region. Organic electroluminescence device.

18. An electronic device equipped with the organic electroluminescence device according to any one of claims 8 to 17.

Images