Compound, organic electroluminescence element, and electronic device

Abstract

The present application relates to a compound, an organic electroluminescence element, and an electronic device. According to the present application, a compound represented by the following formula (1) is provided.

Description

Technical Field

[0001] This invention relates to novel compounds, organic electroluminescent elements, and electronic devices. Background Technology

[0002] When a voltage is applied to an organic electroluminescent element (hereinafter also referred to as an organic EL element), holes are injected from the anode and electrons from the cathode into the light-emitting layer, respectively. Subsequently, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] The performance of previous organic EL devices was not yet sufficient. In order to improve the device performance, organic EL devices have been gradually improved, but further high performance is still required.

[0004] Patent document 1 discloses a compound with a specific structure for use in organic EL elements.

[0005] Existing technical documents Existing technical documents Patent documents Patent Document 1: U.S. Patent Application Publication No. 2019 / 229277. Summary of the Invention

[0006] The purpose of this invention is to provide higher performance organic EL devices.

[0007] In order to achieve the above-mentioned objectives, the inventors conducted repeated and in-depth research and discovered that by using a compound with a specific structure in at least one layer of the organic layer of an organic EL element, a high-performance organic EL element can be obtained, thus completing the present invention.

[0008] According to the present invention, the following compounds, etc., may be provided.

[0009] 1. The compound represented by the following formula (1).

[0010] [Chemistry 1] In formula (1), R1~R 11 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0011] Ar1 is Substituted or unsubstituted pyrene, Substituted or unsubstituted benzo[anthracene], or Substituted or unsubstituted benzoxanthine group.

[0012] 2. Organic electroluminescent elements, which have a cathode, anode and One or more organic layers disposed between the aforementioned cathode and the aforementioned anode At least one of the aforementioned organic layers contains the compound described in 1. above.

[0013] 3. An electronic device comprising the organic electroluminescent element described in 2. above.

[0014] According to the present invention, higher performance organic EL elements can be provided. Attached Figure Description

[0015] Figure 1 This is a diagram illustrating a schematic configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

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

[0017] In this specification, in the chemical structural formula, hydrogen atoms, i.e. protium atoms, deuterium atoms, or tritium atoms, are bonded at positions not explicitly indicated by symbols such as "R" or "D" representing deuterium atoms.

[0018] In this specification, the number of cyclic carbon atoms refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded together to form a cyclic structure (e.g., monocyclic compounds, fused-ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of cyclic carbon atoms. The term "number of cyclic carbon atoms" as used below is the same unless otherwise stated. For example, the number of cyclic carbon atoms in a benzene ring is 6, in a naphthalene ring it is 10, in a pyridine ring it is 5, and in a furan ring it is 4. Additionally, for example, the number of cyclic carbon atoms in 9,9-diphenylfluorenyl is 13, and in 9,9'-spirodifluorenyl it is 25.

[0019] Furthermore, when a benzene ring is substituent, for example, with an alkyl group, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in a benzene ring with a substituent alkyl group is 6. Similarly, when a naphthalene ring is substituent, for example, with an alkyl group, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in a naphthalene ring with a substituent alkyl group is 10.

[0020] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds) whose atoms are bonded to form a cyclic structure (e.g., monocyclic, fused-ring, and ring aggregates). Atoms that do not constitute a ring (e.g., hydrogen atoms that end the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Additionally, for example, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring bonded with hydrogen atoms or substituents is 10.

[0021] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon atoms numbering XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, excluding the number of carbon atoms in substituents. Here, "YY" is greater than "XX", where "XX" refers to an integer greater than 1 and "YY" refers to an integer greater than 2.

[0022] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms in the ZZ group when it is unsubstituted, excluding the number of atoms in the substituent group when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1 and "YY" is an integer greater than or equal to 2.

[0023] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0024] In this specification, "unsubstituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0025] Furthermore, in this specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substitution" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0026] Substituents described in this specification The substituents described in this specification will be explained below.

[0027] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" as described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0028] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" specified in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0029] Unless otherwise stated in this specification, the number of carbon atoms in "unsubstituted alkyl" as stated in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0030] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" specified in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0031] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0032] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted cycloalkyl" as described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0033] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0034] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0035] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylene" as described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0036] • "Substituted or unsubstituted aryl groups" As specific examples (Specific Example Group G1) of the "substituted or unsubstituted aryl" described in the present specification, the following unsubstituted aryl (Specific Example Group G1A) and substituted aryl (Specific Example Group G1B) and the like can be mentioned (here, the unsubstituted aryl refers to the case where the "substituted or unsubstituted aryl" is "unsubstituted aryl", and the substituted aryl refers to the case where the "substituted or unsubstituted aryl" is "substituted aryl"). In the present specification, when "aryl" is mentioned alone, it includes both "unsubstituted aryl" and "substituted aryl".

[0037] The "substituted aryl" means that one or more hydrogen atoms of the "unsubstituted aryl" are replaced with substituents. Examples of the "substituted aryl" include groups in which one or more hydrogen atoms of the "unsubstituted aryl" in the following Specific Example Group G1A are replaced with substituents, and examples of the substituted aryl in the following Specific Example Group G1B, and the like. It should be noted that the examples of the "unsubstituted aryl" and the "substituted aryl" listed here are only examples, and the "substituted aryl" described in the present specification further includes groups in which the hydrogen atom bonded to the carbon atom on the aryl itself in the "substituted aryl" of the following Specific Example Group G1B is further replaced with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl" of the following Specific Example Group G1B is further replaced with a substituent.

[0038] ·Unsubstituted aryl (Specific Example Group G1A): phenyl, p-biphenylyl, m-biphenylyl, o-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, phenalenyl, pyrenyl, chrysenyl, benzochrysenyl, triphenylenyl, benzotriphenylenyl, tetracenyl, Pentaphenyl, Fluorine 9,9'-spirodifluorene, benzo[f]fluorene, Dibenzofluorene, Fluoranthene base, Benzofluoranthyl, Perylene, and A monovalent aryl group is derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-1) to (TEMP-15).

[0039] [Chemistry 2] [Chemistry 3] .

[0040] • Substituted aryl groups (specific example group G1B): o-Tolyl, m-Tolyl, p-Tolyl, p-Xylyl, m-Xylyl, o-xylyl, p-isopropylphenyl, m-Isopropylphenyl, o-isopropylphenyl, p-tert-butylphenyl, m-tert-butylphenyl, o-tert-butylphenyl, 3,4,5-Trimethylphenyl 9,9-Dimethylfluorenyl, 9,9-Diphenylfluorenyl 9,9-Bis(4-methylphenyl)fluorenyl, 9,9-Bis(4-isopropylphenyl)fluorenyl, 9,9-Bis(4-tert-butylphenyl)fluorenyl, cyanophenyl, Triphenylsilylphenyl Trimethylsilylphenyl Phenynaphthyl, Naphthylphenyl, and A group formed by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure shown in the aforementioned general formulas (TEMP-1) to (TEMP-15) with substituents.

[0041] • "Substituted or unsubstituted heterocyclic groups" The term "heterocyclic group" as used in this specification refers to a cyclic group containing at least one heteroatom in its cyclic atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0042] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0043] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0044] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group"). In this specification, when "heterocyclic group" is mentioned alone, it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0045] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the group in which the hydrogen atoms of the "unsubstituted heterocyclic group" in Specific Example Group G2A are replaced, and the examples of substituted heterocyclic groups in Specific Example Group G2B. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic group" described in this specification includes groups in Specific Example Group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself are further replaced by substituents, and groups in Specific Example Group G2B where the hydrogen atoms of the substituents are further replaced by substituents.

[0046] Specific example group G2A includes, for example: unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0047] Specific example group G2B includes, for example: the following substituted heterocyclic groups containing nitrogen atoms (specific example group G2B1), substituted heterocyclic groups containing oxygen atoms (specific example group G2B2), substituted heterocyclic groups containing sulfur atoms (specific example group G2B3), and groups formed by replacing one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) with substituents (specific example group G2B4).

[0048] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1): pyrrole, Imidazole group, pyrazolyl, Triazole group, Tetrazolyl, Oxazolyl, Isoxazolyl, Oxadiazole group, Thiazole group, Isothiazolyl, Thiadiazole group, pyridyl, pyridazinyl, Pyrimidine group, Pyrazinyl, Triazine group Indole, Isoindolyl, Indoleazine, Quinazine-based Quinoline, Isoquinoline, Crenoline group Phthaloazine Quinazolinyl, Quinoxaloyl, Benzimidazole group, Indazole group, phenanthroline, phenanthridine, acridine group, Phenazine group, Carbazole group, Benzocarbazolyl, Morpholinyl group phenoxazine group, phenothiazine group, Azacarbazolyl and diazacarbazolyl.

[0049] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2): furanyl, Oxazolyl, Isoxazolyl, Oxadiazole group, Xuton base, Benzofuranyl, Isobenzofuranyl, Dibenzofuranyl, Naphthobenzofuranyl, Benzoxazolyl, Benzisoxazole group, phenoxazine group, Morpholinyl group Dinaphthylfuranyl, Azadibenzofuranyl, diazadibenzofuranyl, Azanaphthalenebenzofuranyl, and Diazanaphthenebenzofuranyl.

[0050] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3): Thiophene group Thiazole group, Isothiazolyl, Thiadiazole group, Benzothiophene (benzothio) Isobenzothiophene (isobenzophenylthio) dibenzothiophene (dibenzophenylthio) Naphthobenzothiophene (naphthobenzobenzyl) Benzothiazolyl, Benzisothiazolyl, phenothiazine group, Dinaphthothiophene (dinaphthophenylthio) Azadibenzothiophene (azadibenzophenylthio) diazadibenzothiophene (diazadibenzophenylthio) Azanaphthobenzothiophene (azanaphthobenzophenylthio) and Diazanaphthenebenzothiophene (diazanaphthenebenzothiophene).

[0051] • A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4): [Chemistry 4] [Chemistry 5] .

[0052] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y AEach can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0053] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the aforementioned general formulas (TEMP-16) to (TEMP-33) contains a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0054] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1): (9-Phenyl)carbazole, (9-Biphenyl)carbazole, (9-Phenyl)phenylcarbazole, (9-Naphthyl)carbazole, Diphenylcarbazole-9-yl, Phenylexacarbazole-9-yl, Methylbenzimidazole, Ethylbenzimidazole, Phenylacetyl, Biphenyltriazine diphenyltriazine group, phenylquinazolinyl, and Biphenylquinazolinyl.

[0055] • Heterocyclic groups containing oxygen atoms (specific example group G2B2): Phenyl dibenzofuranyl, Methyldibenzofuranyl, tert-butyldibenzofuranyl, and The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0056] • Heterocyclic groups containing sulfur atoms (specific example group G2B3): Phenyl dibenzothiophene, Methyldibenzothiophene, tert-butyldibenzothiophene, and The 1-valent residue of [9H-thioxanth-9,9'-[9H]fluorene].

[0057] • A group formed by replacing one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structures shown in the aforementioned general formulas (TEMP-16) to (TEMP-33) with substituents (specific example group G2B4): The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0058] • "Substituted or unsubstituted alkyl groups" As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited (here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl"). Hereinafter, when "alkyl" is mentioned alone, it includes both "unsubstituted alkyl" and "substituted alkyl".

[0059] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by substituents. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkyl" (specific example group G3A) are replaced by substituents, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes straight-chain "unsubstituted alkyl" and branched "unsubstituted alkyl". It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples. The "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl" of specific example group G3B are further replaced by substituents.

[0060] • Unsubstituted alkyl groups (specific example group G3A): methyl, Ethyl, n-propyl, Isopropyl, n-Butyl, Isobutyl, sec-butyl, and tert-butyl.

[0061] • Substituted alkyl groups (specific example group G3B): Heptafluoropropyl (including isomers) Pentafluoroethyl, 2,2,2-Trifluoroethyl, and Trifluoromethyl

[0062] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group"). In this specification, when "alkenyl group" is mentioned alone, it includes both "unsubstituted alkenyl group" and "substituted alkenyl group".

[0063] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by substituents. Specific examples of "substituted alkenyl" include the substituents in the "unsubstituted alkenyl" group (specific example group G4A) and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples. The "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself are further replaced by substituents, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituents are further replaced by substituents.

[0064] • Unsubstituted alkenyl groups (specific example group G4A): vinyl, Allyl 1-Butenyl, 2-Butenyl, and 3-Butenyl.

[0065] • Substituted alkenyl groups (specific example group G4B): 1,3-Butadienyl, 1-Methylvinyl 1-Methylallyl, 1,1-Dimethylallyl, 2-Methylallyl, and 1,2-Dimethylallyl.

[0066] • "Substituted or unsubstituted alkynyl groups" As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) are examples (here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group"). Hereinafter, when "alkynyl group" is mentioned alone, it includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0067] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0068] • Unsubstituted alkynyl group (specific example group G5A): Acetylene group.

[0069] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl"). In this specification, when "cycloalkyl" is mentioned alone, it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0070] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by substituents. Specific examples of "substituted cycloalkyl" include groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" (specific example group G6A) are replaced by substituents, and examples of substituted cycloalkyl (specific example group G6B), etc. It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" of specific example group G6B are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" of specific example group G6B are further replaced by substituents.

[0071] • Unsubstituted cycloalkyl groups (specific example group G6A): Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Adamantyl, 2-Adamantyl, 1-Norbornel alkyl, and 2-Norbornel alkyl.

[0072] • Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl.

[0073] ·"-Si(R 901 (R)902 (R) 903 The group shown in the figure” As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the groups shown (specific example group G7) can be given as follows: -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).

[0074] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0075] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0076] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0077] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0078] In -Si(G1)(G1)(G1), the multiple G1s may be the same or different.

[0079] In -Si(G1)(G2)(G2), the multiple G2s may be the same or different.

[0080] In -Si(G1)(G1)(G2), multiple G1s may be the same or different.

[0081] In -Si(G2)(G2)(G2), the multiple G2s may be the same or different.

[0082] In -Si(G3)(G3)(G3), the multiple G3s may be the same or different.

[0083] In -Si(G6)(G6)(G6), the multiple G6s may be the same or different.

[0084] ·"-O-(R 904 The group shown in the figure” As described in this specification, -O-(R) 904 Specific examples of the groups shown (specific example group G8) can be given as follows: -O(G1) -O(G2) -O (G3), and -O (G6).

[0085] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0086] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0087] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0088] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0089] • "-S-(R 905 The group shown in the figure” As described in this specification, -S-(R) 905 Specific examples of the groups shown (specific example group G9) can be given as follows: -S (G1) -S (G2) -S (G3), and -S (G6).

[0090] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0091] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0092] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0093] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0094] ·"-N(R 906 (R) 907 The group shown in the figure” As described in this specification, -N(R) 906 (R) 907 Specific examples of the groups shown (specific example group G10) can be given as follows: -N(G1)(G1) -N(G2)(G2), -N(G1)(G2) -N(G3)(G3), and -N(G6)(G6).

[0095] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0096] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0097] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0098] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0099] In -N(G1)(G1), multiple G1s may be the same or different.

[0100] In -N(G2)(G2), multiple G2s may be the same or different.

[0101] In -N(G3)(G3), multiple G3s may be the same or different.

[0102] The multiple G6 values ​​in -N(G6) (G6) may be the same or different. • "Halogen atom" Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0103] • "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" are replaced by fluorine atoms (perfluoroalkyl). The number of carbon atoms in the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl" are replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl" are further replaced by substituents, and groups in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl" are further replaced by substituents. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in the aforementioned "alkyl" (specific example group G3) in which one or more hydrogen atoms are replaced by fluorine atoms.

[0104] • "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" is replaced by a halogen atom, and also includes groups in which all hydrogen atoms bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of the "haloalkyl" are replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl" are further replaced by a substituent, and groups in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl" are further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in the aforementioned "alkyl" (specific example group G3) in which one or more hydrogen atoms are replaced by halogen atoms. Sometimes haloalkyl is referred to as alkyl halide.

[0105] • "Substituted or unsubstituted alkoxy groups" As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, there is a group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.

[0106] • "Substituted or unsubstituted alkylthio groups" As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.

[0107] • "Substituted or unsubstituted aryloxy groups" As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of cyclic 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.

[0108] • "Substituted or unsubstituted arylthio groups" As a specific example of "substituted or unsubstituted aryl thiogroup" as described in this specification, it is the group indicated by -S (G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of cyclic carbon atoms of the "unsubstituted aryl thiogroup" is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.

[0109] • "Substituted or unsubstituted trialkylsilyl groups" As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0110] • "Substituted or unsubstituted aralkyl groups" As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is a type of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" replaced by "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50 unless otherwise specified in this specification, preferably 7 to 30, and more preferably 7 to 18.

[0111] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0112] The substituted or unsubstituted aryl groups described in this specification are preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, meta-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyrene, phenyl, triphenylene, fluorene, 9,9'-spirodifluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc., unless otherwise specified in this specification.

[0113] The substituted or unsubstituted heterocyclic groups described in this specification are preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole, or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-carbazole. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl, or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophene, etc.

[0114] In this specification, the carbazoyl group, unless otherwise specified herein, refers to any of the following groups.

[0115] [Chemistry 6] In this specification, (9-phenyl)carbazolyl refers to any of the following groups unless otherwise specified in this specification.

[0116] [Chemistry 7] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding site.

[0117] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any of the following groups unless otherwise specified in this specification.

[0118] [Chemistry 8] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * indicates the bonding site.

[0119] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described in this specification are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl, etc.

[0120] • "Substituted or unsubstituted aryl groups" Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived by removing one hydrogen atom from the aromatic ring of the aforementioned "substituted or unsubstituted aryl group". Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived by removing one hydrogen atom from the aromatic ring of the "substituted or unsubstituted aryl group" described in specific example group G1.

[0121] • "Substituted or unsubstituted divalent heterocyclic groups" Unless otherwise stated, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom from the heterocycle of the aforementioned "substituted or unsubstituted heterocyclic group". Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived by removing one hydrogen atom from the heterocycle of the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0122] • "Substituted or unsubstituted alkylene compounds" Unless otherwise stated, "substituted or unsubstituted alkylene groups" as described in this specification are divalent groups derived by removing one hydrogen atom from the alkyl chain of the aforementioned "substituted or unsubstituted alkylene groups". Specific examples of "substituted or unsubstituted alkylene groups" (specific example group G14) include divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkylene groups" described in specific example group G3.

[0123] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any group of the following general formulas (TEMP-42) to (TEMP-68).

[0124] [Chemistry 9] [Chemistry 10] In the aforementioned general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0125] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * indicates the bonding site.

[0126] [Chemistry 11] In the aforementioned general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0127] Formulas Q9 and Q 10 They can form rings by bonding with each other through single bonds.

[0128] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * indicates the bonding site.

[0129] [Chemistry 12] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0130] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * indicates the bonding site.

[0131] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0132] [Chemistry 13] [Chemistry 14] [Chemistry 15] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0133] [Chemistry 16] [Chemistry 17] [Chemistry 18] [Chemistry 19] In the aforementioned general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0134] The above is an explanation of the substituents described in this specification.

[0135] • "Cases where bonds form rings" In this specification, the phrase "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together, forming a substituted or unsubstituted fused ring by bonding together, or not bonding together" refers to the following: forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together; forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together; and not bonding one or more groups of two or more adjacent elements together.

[0136] The following description addresses the cases of "a substituted or unsubstituted monocyclic ring formed by the mutual bonding of one or more groups of two or more adjacent elements" and "a substituted or unsubstituted fused ring formed by the mutual bonding of one or more groups of two or more adjacent elements" (hereinafter, these cases are sometimes collectively referred to as "the case of forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0137] [Chemistry 20] For example, R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements that constitutes one group is R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0138] The phrase "one or more groups" refers to two or more groups consisting of two or more adjacent elements that can simultaneously form a loop. For example, R 921 With R 922 They bond together to form a ring Q A And at the same time R 925 With R 926 They bond together to form a ring Q B In the case of the anthracene compound represented by the aforementioned general formula (TEMP-103), the anthracene compound is represented by the following general formula (TEMP-104).

[0139] [Chemistry 21] The case of rings formed by "groups consisting of two or more adjacent elements" includes not only the case of group bonding consisting of "two" adjacent elements as in the previous example, but also the case of group bonding consisting of "three or more" adjacent elements. For example, it refers to R. 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923 When the groups of elements Q bond together to form a ring, fused together to form an anthracene matrix, the anthracene compound represented by the aforementioned 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 There are a total of R 922 .

[0140] [Chemistry 22] The formed "monocyclic ring" or "fused ring," as a structure consisting only of rings, can be a saturated ring or an unsaturated ring. Even when a "monocyclic ring" or "fused ring" is formed from "one of the groups consisting of two adjacent rings," the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, the ring Q formed in the aforementioned general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the aforementioned general formula (TEMP-105) A and ring Q C It is a "fused ring". The ring Q of the aforementioned general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q CFusing together to form fused rings. The ring Q of the aforementioned general formula (TEMP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the aforementioned general formula (TEMP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0141] "Unsaturated rings" include not only aromatic hydrocarbon rings and aromatic heterocycles, but also aliphatic hydrocarbon rings with unsaturated bonds (i.e., double and / or triple bonds) in their ring structure (e.g., cyclohexene, cyclohexadiene, etc.) and non-aromatic heterocycles with unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazoline, quinazonium, indoline, isoindoline, etc.). "Saturated rings" include aliphatic hydrocarbon rings without unsaturated bonds, or non-aromatic heterocycles without unsaturated bonds.

[0142] As a specific example of an aromatic hydrocarbon ring, one can cite a structure in which the group listed as a specific example in example group G1 is end-capped with a hydrogen atom.

[0143] As a specific example of an aromatic heterocycle, the structure in which the aromatic heterocycle group is end-capped with a hydrogen atom can be cited as a specific example in specific example group G2.

[0144] As a specific example of an aliphatic hydrocarbon ring, one can cite the structure in which the group listed as a specific example in example group G6 is end-capped with hydrogen atoms.

[0145] "Ring formation" refers to the formation of a ring solely from multiple atoms of the parent skeleton, or from multiple atoms of the parent skeleton combined with one or more arbitrary atoms. For example, R shown in the aforementioned general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The bonded anthracene framework consists of carbon atoms and rings formed with one or more arbitrary atoms. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the carbon atoms of the bonded anthracene skeleton form a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The resulting ring is a benzene ring.

[0146] Here, "any atom" is preferably selected from at least one atom chosen from carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. For any atom (e.g., carbon or nitrogen), bonds that do not form a ring can be terminated by hydrogen atoms or replaced by "any substituents" described later. When any atom other than carbon is included, the resulting ring is a heterocycle.

[0147] Unless otherwise specified in this specification, "one or more arbitrary atoms" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.

[0148] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0149] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0150] Unless otherwise specified in this specification, "monocyclic" is preferably a benzene ring.

[0151] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0152] Unless otherwise stated in this specification, the preferred form is an unsaturated ring consisting of multiple atoms of a parent skeleton and at least 15 atoms selected from carbon, nitrogen, oxygen and sulfur atoms bonded together, forming a substituted or unsubstituted monocyclic ring.

[0153] When a "monocyclic" or "fused-ring" ring has a substituent, the substituent is, for example, "any substituent" as described later. Specific examples of substituents when a "monocyclic" or "fused-ring" ring has a substituent are the substituents described in the section "Substituents described in this specification" above.

[0154] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, "any substituent" as described later. Specific examples of the substituents when the above-mentioned "monocyclic ring" or "fused ring" has a substituent are the substituents described in the section "Substituents described in this specification" above.

[0155] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" ("the case of forming a ring by bonding").

[0156] Substituents in cases of "substituted or unsubstituted" In one embodiment of this specification, the substituent in the aforementioned "substituted or unsubstituted" case (sometimes referred to as "arbitrary substituent" in this specification) is, for example, a group selected from the following groups: Unsubstituted alkyl groups with 1 to 50 carbon atoms Unsubstituted alkenyl groups with 2 to 50 carbon atoms Unsubstituted acetylinyl groups with 2 to 50 carbon atoms Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R) 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R) 906 (R) 907 ), Halogen atom, cyano group, nitro group, Unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms; Here, R 901 ~R 907 Each independently is: hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0157] R 901 When there are more than two, more than two R 901 They are the same or different. R 902 When there are more than two, more than two R 902 They are the same or different. R 903 When there are more than two, more than two R 903They are the same or different. R 904 When there are more than two, more than two R 904 They are the same or different. R 905 When there are more than two, more than two R 905 They are the same or different. R 906 When there are more than two, more than two R 906 They are the same or different. R 907 When there are more than two, more than two R 907 They are the same or different.

[0158] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from groups including: Alkyl groups with 1 to 50 carbon atoms aryl groups with 6 to 50 carbon atoms in the ring, and Heterocyclic groups with 5 to 50 cyclic atoms.

[0159] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from groups including: Alkyl groups with 1 to 18 carbon atoms aryl groups with 6 to 18 carbon atoms in the ring, and Heterocyclic groups with 5 to 18 cyclic atoms.

[0160] Specific examples of each group of any of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described in this specification" above.

[0161] Unless otherwise stated 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.

[0162] Unless otherwise specified in this specification, any substituent may further have substituents. Any further substituents of any substituent are the same as any substituents described above.

[0163] In this specification, the numerical range represented by "AA~BB" refers to the range that includes the value AA listed before "AA~BB" as the lower limit and the value BB listed after "AA~BB" as the upper limit.

[0164] [New Compound] One aspect of the present invention relates to a compound as shown in formula (1).

[0165] [Chemistry 23] In formula (1), R1~R 11 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0166] Ar1 is Substituted or unsubstituted pyrene, Substituted or unsubstituted benzo[anthracene], or Substituted or unsubstituted benzoxanthine group.

[0167] When the compounds of one aspect of the present invention are used in the organic layer of an organic EL device, their device performance can be improved. In particular, by using the compounds of one aspect of the present invention, the external quantum efficiency of the organic EL device can be improved.

[0168] The rationale for the aforementioned effect is not certain, but it is believed that by introducing a specific substituent at the 1-position of the triphenylene skeleton, the triphenylene skeleton and the substituent undergo stereotactic twisting, hindering intermolecular interactions, thereby exhibiting the aforementioned effect.

[0169] In this specification, "oxygen-containing heterocyclic group" refers to a group that contains at least one oxygen atom as a cyclic atom in the heterocycle. As long as it contains at least one oxygen atom as a cyclic atom, there are no particular limitations on the other cyclic atoms. In addition to carbon atoms, it may also contain nitrogen atoms, phosphorus atoms, sulfur atoms, etc.

[0170] Specific examples of monovalent oxygen-containing heterocyclic groups are not limited to these; for example, the specific example groups G2A2, G2A4, G2B2, and G2B4 mentioned above can be cited. However, specific example groups G2A4 and G2B4 are limited to X. A and Y A The case where at least one of them is an oxygen atom.

[0171] In equation (1), from R1~R 11 The groups consisting of two or more adjacent groups in Ar1 are not bonded to each other.

[0172] In one implementation, R1~R 11 Each independently hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0173] In one implementation, R1~R 11 Each independently hydrogen atom, Substituted or unsubstituted phenyl Substituted or unsubstituted naphthyl groups Replaced or unreplaced foetida Substituted or unsubstituted pyrene, Substituted or unsubstituted benzo[anthracene] Substituted or unsubstituted dibenzofluorenyl, Substituted or unsubstituted dibenzofuranyl, Substituted or unsubstituted naphthobenzofuranyl, or Substituted or unsubstituted benzoxanthine group.

[0174] In one implementation, R1~R2, R5~R6, and R9~R 11 It is a hydrogen atom.

[0175] In one implementation, R1~R 11 It is a hydrogen atom.

[0176] Ar1 can have substituents or be unsubstituted.

[0177] Examples of substituents that have substituents include: hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 15 cyclic carbon atoms, and Substituted or unsubstituted monovalent oxygen-containing heterocyclic groups with 5 to 50 cyclic atoms, etc.

[0178] In one embodiment, the substituent when Ar1 has a substituent is: hydrogen atom, Substituted or unsubstituted phenyl, or Substituted or unsubstituted naphthyl groups.

[0179] In one embodiment, Ar1 is a group selected from the following formulas (Ar-1) to (Ar-9).

[0180] [Chemistry 24] [Chemistry 25] [Chemistry 26] [In formula (Ar-1)~(Ar-9), * indicates a bond with the triphenylene skeleton in formula (1).

[0181] R 101 ~R 110 R 201 ~R 212 and R 301 ~R 310 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 15 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group, with 5 to 50 cyclic atoms, either substituted or unsubstituted. In equations (Ar-1) to (Ar-9), R 101 ~R 110 R 201 ~R 212 and R 301 ~R 310 A group consisting of two or more adjacent elements is not bonded to each other.

[0182] In one embodiment, Ar1 is a group selected from the above formulas (Ar-1) to (Ar-6) and (Ar-9).

[0183] In one embodiment, Ar1 is a group selected from the above formulas (Ar-1) to (Ar-6).

[0184] In one embodiment, Ar1 is a group represented by the above formula (Ar-1), (Ar-2), or (Ar-9).

[0185] In one embodiment, Ar1 is a group represented by the above formula (Ar-1) or (Ar-2).

[0186] In one embodiment, Ar1 is a group selected from the above formulas (Ar-3) to (Ar-6).

[0187] In one embodiment, Ar1 is a group represented by the above formula (Ar-2) or (Ar-4).

[0188] In one implementation, R 101 ~R 110 R 201 ~R 212 and R 301 ~R 310 Each independently hydrogen atom, Substituted or unsubstituted phenyl, or Substituted or unsubstituted naphthyl groups.

[0189] In one implementation, R 101 ~R 110 R 201 ~R 212 and R 301 ~R 310 It is a hydrogen atom.

[0190] In one embodiment, the compound represented by formula (1) is a compound represented by any one of the following formulas (1-1) to (1-6).

[0191] [Chemistry 27] [Chemistry 28] In equations (1-1) to (1-6), R1 to R 11 As defined in equation (1) above.

[0192] R 101 ~R 110 R 201 ~R 206 R 208 ~R 212 and R 301 ~R 310 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 15 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group, with 5 to 50 cyclic atoms, either substituted or unsubstituted. In equation (1-1), from R1 to R 11 and R 102 ~R 110的 A group consisting of two or more adjacent elements is not bonded to each other.

[0193] In equation (1-2), from R1 to R 11 R 201 ~R 206 and R 208 ~R 212 A group consisting of two or more adjacent elements is not bonded to each other.

[0194] In equation (1-3), from R1 to R 11 R 101 ~R 103 and R 105 ~R 110 A group consisting of two or more adjacent elements is not bonded to each other.

[0195] In equation (1-4), from R1 to R 11 R 101 and R 103 ~R 110 A group consisting of two or more adjacent elements is not bonded to each other.

[0196] In equation (1-5), from R1 to R 11 R 301 ~R 303 and R 305 ~R 310 A group consisting of two or more adjacent elements is not bonded to each other.

[0197] In equation (1-6), from R1 to R 11 R 301 ~R 308 and R 310 A group consisting of two or more adjacent elements is not bonded to each other.

[0198] In one embodiment, the compound represented by formula (1) is a compound represented by any of the following formulas (1-11) to (1-16).

[0199] [Chemistry 29] [Chemistry 30] In equations (1-11) to (1-16), R3 to R4 and R7 to R8 are defined as in equation (1) above.

[0200] R 106 ~R 109 R 212 R 304 R 308 ~R 309 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 15 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group, with 5 to 50 cyclic atoms, either substituted or unsubstituted. In equations (1-11) to (1-16), the groups R3 and R4 are not bonded to each other, and the groups R7 and R8 are not bonded to each other.

[0201] In one embodiment, the compound represented by formula (1) has at least one deuterium atom.

[0202] In one embodiment, R1~R are hydrogen atoms 11 At least one of them is a deuterium atom.

[0203] In one embodiment, R1~R are alkyl, aryl, or monovalent oxygen-containing heterocyclic groups. 11 At least one of the hydrogen atoms in it is a deuterium atom.

[0204] In one embodiment, at least one of the hydrogen atoms in Ar1 is a deuterium atom.

[0205] In one embodiment, R1~R are hydrogen atoms 11 It is a protium atom. R1~R are alkyl, aryl, or monovalent oxygen-containing heterocyclic groups. 11 The hydrogen atoms it contains are protium atoms. Ar1 contains at least one deuterium atom among its hydrogen atoms.

[0206] In this specification, "having deuterium atoms" means that, among the hydrogen atoms in the compound or group, the proportion of deuterium atoms is greater than that found naturally in at least one hydrogen atom, relative to the total number of protium and deuterium atoms.

[0207] In this specification, a specific hydrogen atom (or R as a hydrogen atom) is referred to as... x (X is an integer used to define the substituent)) "deuterium atom" means that in this hydrogen atom, the proportion of deuterium atoms is greater than that of naturally occurring atoms relative to the total number of protium and deuterium atoms.

[0208] Nuclear magnetic resonance (NMR) devices can confirm that, relative to the total number of protium and deuterium atoms, the proportion of deuterium atoms is greater than that found naturally.

[0209] In this specification, a specific hydrogen atom (or R as a hydrogen atom) is referred to as... x (X refers to the number or symbol used to define the substituent)) "for protium atom" means that in this hydrogen atom, the proportion of deuterium atoms relative to the total number of protium and deuterium atoms is as follows:

[0210] Nuclear magnetic resonance (NMR) devices can confirm that, relative to the total number of protium and deuterium atoms, the proportion of deuterium atoms is below the naturally occurring ratio.

[0211] In one embodiment, the substituent in formula (1), referred to as "substituted or unsubstituted", is Alkyl groups with 1 to 50 carbon atoms Alkenes with 2 to 50 carbon atoms Alkynes with 2 to 50 carbon atoms Cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 ), Halogen atom, cyano group, nitro group, aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms.

[0212] R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0213] In one embodiment, the substituent in formula (1), referred to as "substituted or unsubstituted," is selected from... Alkyl groups with 1 to 50 carbon atoms aryl groups with 6-50 carbon atoms in the ring and Groups in heterocyclic groups with 5 to 50 cyclic atoms.

[0214] In one embodiment, the substituent in formula (1), referred to as "substituted or unsubstituted," is selected from... Alkyl groups with 1 to 50 carbon atoms aryl groups with 6-15 carbon atoms in the ring, and Groups in heterocyclic groups with 5 to 50 cyclic atoms.

[0215] In one embodiment, the substituent in formula (1), referred to as "substituted or unsubstituted," is selected from... Alkyl groups with 1 to 50 carbon atoms aryl groups with 6-15 carbon atoms in the ring, and Groups in oxygen-containing heterocyclic groups with 5 to 50 cyclic atoms.

[0216] In one embodiment, the substituent in formula (1), referred to as "substituted or unsubstituted," is selected from... Alkyl groups with 1 to 18 carbon atoms aryl groups with 6-18 carbon atoms in the ring, and Groups in heterocyclic groups with 5 to 18 cyclic atoms.

[0217] In one embodiment, the substituent in formula (1), referred to as "substituted or unsubstituted," is selected from... Alkyl groups with 1 to 18 carbon atoms aryl groups with 6-15 carbon atoms in the ring, and Groups in heterocyclic groups with 5 to 18 cyclic atoms.

[0218] In one embodiment, the substituent in formula (1), referred to as "substituted or unsubstituted," is selected from... Alkyl groups with 1 to 18 carbon atoms aryl groups with 6-15 carbon atoms in the ring, and Groups in oxygen-containing heterocyclic groups with 5 to 18 cyclic atoms.

[0219] The compounds involved in one aspect of the present invention can be synthesized, according to the embodiments, by using known substitution reactions and starting materials consistent with the target compound.

[0220] As one aspect of the invention, the compounds involved include, for example, the compounds described in the embodiments.

[0221] The following describes specific examples of compounds involved in one aspect of the present invention, but these are merely illustrative examples, and the compounds involved in one aspect of the present invention are not limited to the specific examples described below.

[0222] [Chemistry 31] [Chemistry 32] [Chemistry 33] [Chemistry 34] [Chemistry 35] [Chemistry 36] [Chemistry 37] [Chemistry 38] [Chemistry 39] [Chemistry 40] [Chemistry 41] [Chemistry 42] [Chemistry 43] [Chemistry 44] [Chemistry 45] [Chemistry 46] [Chemistry 47] [Chemistry 48] [Chemistry 49] [Transformation 50] [Chemistry 51] [Chemistry 52] [Chemistry 53] [Chemistry 54] [Chemistry 55] [Chemistry 56] [Chemistry 57] [Chem.58] [Chemistry 59] [Transformation 60] [Chemistry 61] [Chemistry 62] [Chemistry 63] [Chemistry 64] [Chemistry 65] [Chemistry 66] [Chemistry 67] [Chemistry 68] [Chemistry 69] [Chemistry 70] [Chemistry 71] [Chemistry 72] .

[0223] Materials for Organic Electroluminescent Devices The compounds involved in one aspect of the present invention are useful as materials for organic EL elements, for example as materials used in the light-emitting layer of organic EL elements.

[0224] [Organic EL Components] An organic EL element relating to one aspect of the present invention will be described.

[0225] An organic EL element according to one aspect of the present invention has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains a compound according to one aspect of the present invention (a compound represented by formula (1)).

[0226] One aspect of the present invention relates to an organic EL element that, by having the above-described configuration, can improve performance.

[0227] In one embodiment, the light source comprises, in sequence, an anode, a light-emitting layer, and a cathode, wherein at least one organic layer of the light-emitting layer comprises a compound according to one aspect of the present invention.

[0228] In one embodiment, the organic EL element according to one aspect of the present invention further comprises a compound represented by any one of the following formulas (D11) to (D41).

[0229] [Chemistry 73] Equations (D11) to (D41) are described below.

[0230] (The compound represented by formula (D11)) The compound represented by formula (D11) will be described.

[0231] [Chemistry 74] In formula (D11), Each of the three Zs is an independent CR a Or nitrogen atoms.

[0232] Rings A1 and A2 are each independent of each other. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0233] R a When there are multiple R, it is composed of multiple R a One or more groups consisting of two or more adjacent elements They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They are not bonded together.

[0234] nD11 and nD12 are each independently 0, 1, 2, 3, or 4.

[0235] R b When there are multiple R, it is composed of multiple R b One or more groups consisting of two or more adjacent elements They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They are not bonded together.

[0236] R c When there are multiple R, it is composed of multiple R cOne or more groups consisting of two or more adjacent elements They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They are not bonded together.

[0237] R that does not form the aforementioned single ring and the aforementioned fused ring a R b and R c Each independently Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 ), Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0238] R 901 ~R 907 As defined in equation (1) above. The "aromatic hydrocarbon rings" of rings A1 and A2 have the same structure as those of compounds with hydrogen atoms introduced into the "aryl group having 6 to 50 carbon atoms".

[0239] The "aromatic hydrocarbon rings" of A1 and A2 contain two carbon atoms on the fused 2-ring structure at the center of the aforementioned formula (D11) as cyclic atoms.

[0240] As a specific example of "aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms", compounds in which hydrogen atoms are introduced into "substituted or unsubstituted aryl groups" as described in Specific Example Group G1 can be cited.

[0241] The "heterocyclic" rings A1 and A2 have the same structure as the compounds with hydrogen atoms introduced into the "heterocyclic groups with 5 to 50 cyclic atoms" mentioned above.

[0242] The "heterocyclic" rings A1 and A2 contain two carbon atoms on the fused 2-ring structure at the center of the aforementioned formula (D11) as cyclic atoms.

[0243] As a specific example of "a heterocycle with 5 to 50 cyclic atoms, whether substituted or unsubstituted", compounds in which hydrogen atoms are introduced into the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2 can be cited.

[0244] Rb is bonded to any carbon atom that forms an aromatic hydrocarbon ring as an Al ring, or to any atom that forms a heterocyclic ring as an Al ring.

[0245] Rc is bonded to any carbon atom that forms an aromatic hydrocarbon ring as an A2 ring, or to any atom that forms a heterocyclic ring as an A2 ring.

[0246] In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D11a).

[0247] In one embodiment, at least two of Ra, Rb, and Rc are groups represented by the following formula (D11a).

[0248] [Chemistry 75] In formula (D11a), L D101 for single bond, Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or A divalent heterocyclic group with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0249] Ar D101 for substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the following formula (D11b).

[0250] [Chemistry 76] (In formula (D11b),) L D102 and L D103 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or A divalent heterocyclic group with 5 to 30 cyclic atoms, substituted or unsubstituted.

[0251] Includes ArD102 and Ar D103 group They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They are not bonded together.

[0252] The aforementioned Ar does not form monocyclic or fused rings D102 and Ar D103 Each independently Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group, substituted or unsubstituted, with 5 to 50 cyclic atoms. The following describes specific examples of compounds represented by formula (D11), but they are merely illustrative and the compounds represented by formula (D11) are not limited to the specific examples described below.

[0253] [Chemistry 77] (The compound represented by formula (D21)) The compound represented by formula (D21) will be described.

[0254] [Chemistry 78] In formula (D21), R D201 With R D202 R D202 With R D203 and R D203 With R D204 At least one group of them are bonded to each other to form a divalent group as shown in the following formula (D22).

[0255] R D205 With R D206 R D206 With R D207 and R D207 With R D208 At least one group of them is bonded to each other to form a divalent group as shown in the following formula (D23).

[0256] [Chemistry 79] (R D211 ~R D214 R without forming the divalent group shown in formula (D22) D201 ~R D204 At least one of them is a monovalent group as shown in the following formula (D24).

[0257] R D221 ~RD224 And R without the divalent group shown in formula (D23) D205 ~R D208 At least one of them is a monovalent group as shown in the following formula (D24).

[0258] X D2 For oxygen atoms, sulfur atoms, or NR D209 .

[0259] R that does not form the divalent groups shown in formulas (D22) and (D23) and is not the monovalent group shown in formula (D24) D201 ~R D208 R that is not a monovalent group as shown in the aforementioned formula (D24) D211 ~R D214 and R D221 ~R D224 and R D209 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 ), Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0260] [Chemistry 80] (In formula (D24),) Ar D201 and Ar D202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0261] LD201 ~L D203 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or A divalent linking group formed by bonding 2 to 4 groups selected from substituted or unsubstituted aryl groups with 6 to 30 carbon atoms and substituted or unsubstituted divalent heterocyclic groups with 5 to 30 carbon atoms.

[0262] * indicates the bonding position with the ring structure shown in formula (D21), or the group shown in formula (D22) or (D23). R 901 ~R 907 As defined in equation (1) above. In formula (D21), the positions of the divalent groups shown in formula (D22) and formula (D23) are not particularly limited and can be in R. D201 ~R D208 The group forms at possible positions.

[0263] As for the compounds represented by formula (D21), in addition to the compounds described in International Publication No. 2014 / 104144, the following compounds may be cited as specific examples, but they are only examples and the compounds represented by formula (D21) are not limited to the following specific examples.

[0264] [Chemistry 81] (The compound represented by formula (D31)) The compound represented by formula (D31) will be described.

[0265] [Chemistry 82] In formula (D31), By R D301 ~R D307 and R D311 ~R D317 Two or more adjacent rings are bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together.

[0266] R that does not form the aforementioned single ring and the aforementioned fused ring D301 ~R D307 and R D311 ~R D317 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 ), Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0267] R D321 and R D322 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 ), Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0268] R 901 ~R 907 As defined in equation (1) above. "by R" D301 ~R D307 and RD311 ~R D317 A group consisting of two or more adjacent elements, for example, R D301 With R D302 The group composed of R D302 With R D303 The group composed of R D303 With R D304 The group composed of R D305 With R D306 The group composed of R D306 With R D307 The group composed of R D301 With R D302 With R D303 Groups and combinations.

[0269] In one implementation, R D301 ~R D307 and R D311 ~R D317 At least one of them is -N(R) 906 (R) 907 ).

[0270] In one implementation, R D301 ~R D307 and R D311 ~R D317 The two are -N(R) 906 (R) 907 ).

[0271] In one implementation, R D301 ~R D307 and R D311 ~R D317 Each independently hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0272] The following describes specific examples of compounds represented by formula (D31), but they are merely illustrative and the compounds represented by formula (D31) are not limited to the specific examples described below.

[0273] [Chemistry 83] [Chemistry 84] (The compound represented by formula (D41)) The compound represented by formula (D41) will be described.

[0274] [Chemistry 85] In formula (D41), Rings a, b, and c are each independently... Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0275] R D401 and R D402 Each ring independently bonds to the aforementioned a-ring, b-ring, or c-ring to form a substituted or unsubstituted heterocycle, or no ring at all.

[0276] R that does not form the aforementioned heterocycle D401 and R D402 Each independently Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group, with 5 to 50 cyclic atoms, either substituted or unsubstituted. Rings a, b, and c are rings fused with a fused 2-ring structure at the center of formula (D41) consisting of a B atom and two N atoms (a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocycle with 5 to 50 cyclic carbon atoms).

[0277] The "aromatic hydrocarbon rings" of rings a, b, and c have the same structure as those of compounds in which hydrogen atoms are introduced into the "aryl" group. The "aromatic hydrocarbon ring" of ring a includes three carbon atoms in the fused 2-ring structure at the center of formula (D41) as cyclic atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms in the fused 2-ring structure at the center of formula (D41) as cyclic atoms. Specific examples of "aromatic hydrocarbon rings with 6 to 50 substituted or unsubstituted cyclic carbon atoms" include compounds in specific example group G1 in which hydrogen atoms are introduced into the "aryl" group.

[0278] The "heterocycles" of rings a, b, and c have the same structure as compounds in which hydrogen atoms are introduced into the aforementioned "heterocyclic group". The "heterocycle" of ring a includes the three carbon atoms of the fused 2-ring structure at the center of formula (D41) as cyclic atoms. The "heterocycles" of rings b and c include the two carbon atoms of the fused 2-ring structure at the center of formula (D41) as cyclic atoms. As a specific example of "heterocycles with 5 to 50 substituted or unsubstituted cyclic atoms", compounds in which hydrogen atoms are introduced into the "heterocyclic group" as described in specific example group G2 can be cited.

[0279] R D401 and R D402 Each ring can independently bond with ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. In this case, the heterocycle contains the nitrogen atom in the fused 2-ring structure at the center of formula (D41). The heterocycle in this case may contain heteroatoms other than the nitrogen atom. R D401 and R D402 Bonding with ring a, ring b, or ring c specifically refers to the bonding between atoms constituting ring a, ring b, or ring c and atoms constituting ring R. D401 and R D402 Atomic bonding. For example, R D401 It can bond with an α ring to form a ring containing R D401 A nitrogen-containing heterocycle obtained by fusion of a ring with an a ring, comprising two rings (or three or more rings). Specific examples of such nitrogen-containing heterocycles include compounds in specific example group G2 that correspond to heterocyclic groups containing two or more nitrogen rings fused together.

[0280] R D401 In the case of ring bonding with b, R D402 The case of α-ring bonding and R D402 The cases involving bonding with the c-ring are the same as described above.

[0281] In one embodiment, rings a, b, and c in formula (D41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring with 6 to 50 carbon atoms.

[0282] In one embodiment, rings a, b, and c in formula (D41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0283] In one implementation, R in equation (D41) D401 and R D402 Each is independently an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted, or a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms, preferably an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[0284] In one embodiment, the compound represented by formula (D41) is the compound represented by formula (D42) below.

[0285] [Chemistry 86] (In formula (D42),) R D401A With selection from R D411 and R D421 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they are not bonded at all. R D402A With selection from R D413 and R D414 One or more of them are bonded together to form substituted or unsubstituted heterocycles, or they are not bonded at all.

[0286] R does not form the aforementioned substituted or unsubstituted heterocycles D401A and R D402A Each independently Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0287] R D411 ~R D421 Two or more adjacent rings are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other.

[0288] R does not form the aforementioned substituted or unsubstituted heterocycles or the aforementioned substituted or unsubstituted saturated or unsaturated rings. D411 ~R D421 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906(R) 907 ), Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0289] R 901 ~R 907 As defined in equation (1) above. R in equation (D42) D401A and R D402A For R corresponding to equation (D41) D401 and R D402 . group.

[0290] For example, R D401A With R D411 These can be bonded to form nitrogen-containing heterocycles with two-ring fusion (or three-ring fusion) by fusion of the rings containing them with a benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocycles include compounds in specific example group G2 corresponding to heterocyclic groups with two or more fused nitrogen rings. R D401A With R D412 Bonding situation, R D402A With R D413 Bonding cases and R D402A With R D414 The bonding situations are the same as described above.

[0291] R D411 ~R D421 Two or more adjacent rings in a ring can bond together to form substituted or unsubstituted saturated or unsaturated rings. For example, R D411 With R D412 They can be bonded to form structures in which the bonded 6-membered rings are fused with benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings, etc. The fused rings formed can be naphthalene rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.

[0292] In one implementation, R does not participate in cyclic formation. D411 ~R D421 Each of the following groups is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic carbon atoms.

[0293] In one implementation, R does not participate in cyclic formation. D411 ~R D421Each is independently a hydrogen atom, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0294] In one implementation, R does not participate in cyclic formation. D411 ~R D421 Alkyl groups, each consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms.

[0295] In one implementation, R does not participate in cyclic formation. D411 ~R D421 Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms, R D411 ~R D421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0296] In one embodiment, the compound represented by the aforementioned formula (D41) is the compound represented by the following formula (D44).

[0297] [Chemistry 87] (In formula (D44),) X D401 It can be O or S.

[0298] R D401B With selection from R D487 and R D497 One or more of them are bonded together to form a substituted or unsubstituted heterocycle, or they are not bonded at all. R D402B With selection from R D489 and R D490 One or more of them are bonded together to form substituted or unsubstituted heterocycles, or they are not bonded at all.

[0299] R does not form the aforementioned substituted or unsubstituted heterocycles D401B and R D402B Each independently Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0300] R D487 ~R D497Two or more adjacent rings are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other.

[0301] R does not form the aforementioned substituted or unsubstituted heterocycles or the aforementioned substituted or unsubstituted saturated or unsaturated rings. D487 ~R D497 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 (R) 907 ), Halogen atom, cyano group, nitro group, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0302] R 901 ~R 907 As defined in equation (1) above. In one implementation, R D401B and R D402B Each is independently an alkyl group with 1 to 50 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0303] In one implementation, R D487 ~R D497 Each is independently an alkyl group with 1 to 50 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[0304] The compound shown in formula (D41) first connects rings a, b, and c via a linking group (containing NR). D401 Groups and containing NR D402The intermediate is produced by bonding the a, b, and c rings together with a linking group (a group containing B) (reaction 1), and the final product is produced by bonding the a, b, and c rings together with a linking group (a group containing B) (reaction 2). Amination reactions such as the Buchwald-Hartwig reaction can be used in reaction 1. Tandem hetero-Friedrich-Kreutz reaction can be used in reaction 2.

[0305] The following describes specific examples of compounds represented by formula (D41), but these are merely illustrative examples and the compounds represented by formula (D41) are not limited to the specific examples described below.

[0306] [Chemistry 88] [Chemistry 89] [Chemistry 90] [Chemistry 91] [Chemistry 92] [Chemistry 93] [Chemistry 94] [Chemistry 95] [Chemistry 96] [Chemistry 97] [Chem. 98] In addition to the compounds shown in formulas (D11), (D12), (D13) or (D14) above, the aforementioned light-emitting layer may also use compounds such as those shown below.

[0307] [Chemistry 99] In one embodiment, the aforementioned light-emitting layer has a compound represented by the formula (D41) above.

[0308] In one embodiment, the aforementioned light-emitting layer comprises a first layer and a second layer from the anode side, wherein the aforementioned first layer comprises a compound (the compound shown in formula (1)) according to one aspect of the present invention.

[0309] In one embodiment, the aforementioned light-emitting layer has a first layer, a second layer, and more than one layer from the anode side, wherein the aforementioned first layer contains a compound (the compound shown in formula (1)) according to one aspect of the present invention.

[0310] In one embodiment, the first layer contains a compound according to one aspect of the present invention and a compound represented by any of the aforementioned formulas (D11) to (D41).

[0311] In one embodiment, the first layer, as the host material (sometimes also called the matrix material), contains the compound involved in one aspect of the invention.

[0312] In one embodiment, the first layer further comprises a dopant material.

[0313] In one embodiment, the first layer, as a dopant material (sometimes also referred to as a guest material, emitter, or luminescent material), comprises a compound represented by any of the formulas (D11) to (D41) above.

[0314] In one embodiment, the first layer contains more than 1.1% by mass, 1.2% by mass, or 1.5% by mass of dopant material of the total mass of the first layer.

[0315] In one embodiment, the first layer contains dopant material of 10% or less, 7% or less, or 5% or less of the total mass of the first layer.

[0316] In one embodiment, the first layer contains 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the main material of the total mass of the first layer.

[0317] In one embodiment, the first layer contains less than 99% by mass of the main material of the first layer.

[0318] The first layer may contain materials other than the host material and dopant materials.

[0319] The first layer may contain only one host material or two or more. The first layer may contain only one dopant material or two or more.

[0320] In one embodiment, the first layer comprises a compound according to one aspect of the present invention and a compound represented by the following formula (H2).

[0321] [Chemistry 100] In formula (H2), R H201 ~R H208 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted alkyl halogroups with 1 to 50 carbon atoms Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Aryl groups with 7 to 50 carbon atoms, substituted or unsubstituted -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, Nitro, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0322] L H201 and L H202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 cyclic carbon atoms, or A divalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0323] Ar H201 and Ar H202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0324] R 901 R 902 R 903 R 904 R 905 R 906R 907 R 801 and R 802 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0325] R 901 When multiple R exist, multiple R 901 They are the same or different. R 902 When multiple R exist, multiple R 902 They are the same or different. R 903 When multiple R exist, multiple R 903 They are the same or different. R 904 When multiple R exist, multiple R 904 They are the same or different. R 905 When multiple R exist, multiple R 905 They are the same or different. R 906 When multiple R exist, multiple R 906 They are the same or different. R 907 When multiple R exist, multiple R 907 They are the same or different. R 801 When multiple R exist, multiple R 801 They are the same or different. R 802 When multiple R exist, multiple R 802 They are the same or different.

[0326] In one implementation, R H201 ~R H208 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted alkyl halogroups with 1 to 50 carbon atoms Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Aryl groups with 7 to 50 carbon atoms, substituted or unsubstituted -C(=O)R 801 The groups shown -COOR 802 The groups shown Halogen atoms, cyano, or Nitro, L H201 and L H202 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 50 cyclic carbon atoms, or Divalent heterocyclic groups with 5-50 cyclic atoms, substituted or unsubstituted. Ar H201 and Ar H202 Each independently Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0327] In one implementation, L H201 and L H202 Each independently single key, or A substituted or unsubstituted cyclic aryl group with 6 to 50 carbon atoms.

[0328] In one implementation, Ar H201 and Ar H202 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 cyclic carbon atoms.

[0329] In one implementation, Ar H201 and Ar H202 Each independently Phenyl, Naphthyl, Fiki, Biphenyl Triphenyl Diphenylfluorenyl, Dimethylfluorenyl, benzodiphenylfluorenyl, benzodimethylfluorenyl, Dibenzofuranyl, Dibenzothiophene group, Naphthobenzofuranyl, or Naphthobenzothiophene group.

[0330] In one embodiment, the compound represented by formula (H2) is selected from the compounds represented by formulas (H201) to (H209) below.

[0331] [Chemistry 101] [Chemistry 102] [Chemistry 103] In formula (H201)~(H209), L H201 and Ar H201 L in the aforementioned formula (H2) H201 and Ar H201 They have the same meaning.

[0332] R H201 ~R H208 Each independently relates to R in the aforementioned equation (2). H201 ~R H208 They have the same meaning.

[0333] In formulas (H201) to (H209), hydrogen atoms on the phenyl, phenylene, naphthyl, and naphthyl groups are omitted. In other words, hydrogen atoms are bonded to the carbon atoms that constitute the phenyl, phenylene, naphthyl, and naphthyl groups, except for those that are structurally bonded to adjacent carbon atoms.

[0334] For example, in formula (H201), the phenyl group present on the left side of the paper relative to the anthracene skeleton is an unsubstituted phenyl group, with one hydrogen atom bonded to each of the carbon atoms at positions 1 to 5.

[0335] The following describes specific examples of compounds represented by formula (H2), but these are merely illustrative examples, and the compounds represented by formula (H2) are not limited to the specific examples described below.

[0336] [Chemistry 104] [Chemistry 105] [Chemistry 106] .

[0337] The luminescent layer is a layer containing a highly luminescent substance, and various materials can be used. For example, in addition to compounds shown in any of formulas (D11) to (D41) above, fluorescent compounds and phosphorescent compounds can be used as highly luminescent substances. Fluorescent compounds are compounds that can emit light from a singlet excited state, and phosphorescent compounds are compounds that can emit light from a triplet excited state.

[0338] Blue-based fluorescent materials that can be used in the luminescent layer include pyrene derivatives, styrene-amine derivatives, phenylene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Green-based fluorescent materials that can be used in the luminescent layer include aromatic amine derivatives. Red-based fluorescent materials that can be used in the luminescent layer include butane derivatives and diamine derivatives.

[0339] Blue phosphorescent materials that can be used in the luminescent layer employ metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Green phosphorescent materials that can be used in the luminescent layer employ iridium complexes. Red phosphorescent materials that can be used in the luminescent layer employ metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes.

[0340] As the luminescent layer, it can be configured such that the aforementioned highly luminescent substance (guest material) is dispersed in other substances (host material). As the substance used to disperse the highly luminescent substance, various substances can be used in addition to the materials used in the present invention described above (the compounds involved in one aspect of the present invention), and it is preferable to use a substance with a higher lowest empty orbital energy level (LUMO level) and a lower highest occupied orbital energy level (HOMO level) compared to the highly luminescent substance.

[0341] As the main material used to disperse highly luminescent substances, the following are used: 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthrene-rholine derivatives; 3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or β-derived derivatives; and 4) aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[0342] Alternatively, delayed fluorescence (thermally activated delayed fluorescence) compounds can also be used as the host material. The luminescent layer preferably comprises the materials used in this invention as described above and the delayed fluorescence host compound.

[0343] In addition to the materials used in this invention as described above, the light-emitting layer may also contain other substances as described above, or it may not contain any of them.

[0344] (Level 2) The second layer contains at least one compound different from the first layer described above. In one embodiment, the second layer contains a host material (second host material). As the host material, substances listed above that serve as the host material (first host material) of the first layer can be used.

[0345] In one embodiment, the second host material is a compound different from the first host material contained in the first layer.

[0346] Furthermore, delayed fluorescence (thermally activated delayed fluorescence) compounds can also be used as the host material. The luminescent layer may also contain the compounds described above, as well as the delayed fluorescence host compound.

[0347] In one embodiment, the second layer further comprises a dopant material (the second dopant material). As the dopant material, substances listed above as the dopant material (the first dopant material) of the first layer can be used.

[0348] In one embodiment, the second dopant material is a compound represented by any one of the formulas (D11) to (D41) above.

[0349] In one embodiment, the second dopant material is a compound different from the first dopant material.

[0350] In one embodiment, the second dopant material is the same compound as the first dopant material.

[0351] In one embodiment, the second layer contains more than 1.1% by mass, 1.2% by mass, or 1.5% by mass of the total mass of the second layer as dopant material.

[0352] In one embodiment, the second layer contains dopant material of 10% or less, 7% or less, or 5% or less of the total mass of the second layer.

[0353] In one embodiment, the second layer contains 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the main material of the total mass of the second layer.

[0354] In one embodiment, the second layer contains less than 99% by mass of the main material of the second layer.

[0355] The second layer may contain materials other than the host material and dopant materials.

[0356] The second layer may contain only one host material or two or more. The second layer may contain only one dopant material or two or more.

[0357] The second layer can be either a fluorescent or phosphorescent luminescent layer.

[0358] In one embodiment, the second layer is a fluorescent light-emitting layer.

[0359] In one embodiment, an organic EL element according to one aspect of the present invention has a hole transport region between the aforementioned anode and the aforementioned light-emitting layer.

[0360] In one embodiment, an organic EL element according to one aspect of the present invention has an electron transport region between the aforementioned cathode and the aforementioned light-emitting layer.

[0361] Reference Figure 1 This invention describes the general configuration of an organic EL element according to one aspect of the present invention.

[0362] In one embodiment, an organic EL element 1 according to one aspect of the present invention includes: a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, a hole transport region 4 located between the anode 3 and the light-emitting layer 5, and an electron transport region 6 located between the light-emitting layer 5 and the cathode 10.

[0363] As a representative component of the organic EL element of the present invention, a structure in which the following structure is stacked on a substrate can be exemplified.

[0364] (1) Anode / Light-emitting layer / Cathode (2) Anode / hole transport region / light-emitting layer / cathode (3) Anode / Light-emitting layer / Electron transport region / Cathode (4) Anode / Hole transport region / Light-emitting layer / Electron transport region / Cathode (“ / ” indicates that the layers are adjacent and stacked.)

[0365] The hole transport region is a collective term for one or more layers disposed between the anode and the light-emitting layer. For example, from the light-emitting layer side, the hole transport region is composed of layers referred to later as an electron blocking layer, a hole transport layer, and a hole injection layer. It can be a stacked structure containing all of these layers, or it can be composed of only a portion of these layers. Furthermore, for each of the above layers, two or more types of layers can be used; for example, two different hole transport layers can be stacked together.

[0366] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0367] The electron transport region is a collective term for one or more layers disposed between the cathode and the light-emitting layer. For example, starting from the light-emitting layer side, the electron transport region is composed of layers referred to later as a hole blocking layer, exciton blocking layer, electron transport layer, and electron injection layer. It can be a stacked structure containing all of these layers, or it can be composed of only a portion of these layers. Furthermore, for each of the above layers, two or more types of layers can be used; for example, two different electron transport layers can be stacked together.

[0368] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0369] Hereinafter, components that can be used in an organic EL element according to one aspect of the present invention and materials other than the compounds described above that constitute each layer will be described.

[0370] (Substrate) The substrate serves as a support for the light-emitting element. Materials such as glass, quartz, and plastic can be used as substrates. Flexible substrates can also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate or polyvinyl chloride.

[0371] (anode) The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples include indium tin oxide (ITO), silicon- or silicon-oxide-containing indium tin oxide, indium zinc oxide, tungsten oxide, zinc oxide-containing indium oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride).

[0372] (hole injection layer) A hole injection layer is a layer containing a substance with high hole injection capacity. Substances with high hole injection capacity may include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymers (oligomers, dendritic macromolecules, polymers, etc.).

[0373] (Hole transport layer) The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used. If the substance has higher hole transport capacity than electron transport capacity, substances other than these can also be used. It should be noted that the layer containing the substance with high hole transport capacity can be not only a single layer, but also a layer formed by stacking two or more layers containing the above-mentioned substances.

[0374] (Electron blocking layer, hole blocking layer, exciton blocking layer) Electron blocking layers, hole blocking layers, exciton (triple state) blocking layers, etc., can be set adjacent to the light-emitting layer.

[0375] An electron blocking layer is a layer that prevents electrons from leaking from the luminescent layer to the hole transport layer. A hole blocking layer is a layer that prevents holes from leaking from the luminescent layer to the electron transport layer. An exciton blocking layer is a layer that prevents excitons generated in the luminescent layer from diffusing into adjacent layers, thus confining the excitons within the luminescent layer.

[0376] (Electron transport layer) The electron transport layer is a layer containing substances with high electron transport capacity. The following can be used in the electron transport layer: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymeric compounds.

[0377] (Electron injection layer) The electron-injection layer is a layer containing materials with high electron-injection potential. Metal complexes such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium 8-hydroxyquinoline (Liq), as well as lithium oxides (LiO2), can be used in the electron-injection layer. x Alkali metals, alkaline earth metals, or their compounds, etc.

[0378] (cathode) The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[0379] In one aspect of the organic EL element, the film thickness of each layer is not particularly limited. Generally, in order to suppress defects such as pinholes, suppress the applied voltage to a low value, and achieve good luminous efficiency, the thickness is usually preferred to be in the range of several nm to 1 μm.

[0380] In the organic EL element according to one aspect of the present invention, the method of forming each layer is not particularly limited. Formation methods based on conventionally known methods such as vacuum evaporation and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by known methods such as vacuum evaporation, molecular beam evaporation (MBE), or coating methods based on solutions dissolved in solvents, such as immersion coating, spin coating, casting, rod coating, and roll coating.

[0381] [Electronic devices] An electronic device according to one aspect of the present invention is characterized by having an organic EL element according to one aspect of the present invention.

[0382] Specific examples of electronic devices include display components such as organic EL panel assemblies; display devices such as televisions, mobile phones, or personal computers; and light-emitting devices such as lighting or vehicle lamps. Example

[0383] <Compound> The compounds of formula (1) used in the manufacture of the organic EL elements in Examples 1-6 are shown below.

[0384] [Chemistry 107] The comparative compound used in the manufacture of the organic EL element of Comparative Example 1 is shown below.

[0385] [Chemistry 108] The structures of other compounds used in the manufacture of the organic EL elements of Examples 1-6 and Comparative Example 1 are shown below.

[0386] [Chemistry 109] .

[0387] Example 1 <Fabrication of Organic EL Components> Organic EL elements are fabricated as described below.

[0388] A glass substrate (manufactured by Geomatics Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. This resulted in an ITO film thickness of 130nm.

[0389] The cleaned glass substrate with transparent electrodes is mounted on the substrate support of the vacuum evaporation apparatus. First, on the side where the transparent electrodes are formed, compound HA is evaporated to cover the transparent electrodes, forming a hole injection layer with a film thickness of 5 nm.

[0390] Compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[0391] Compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[0392] On the second hole transport layer, compound Inv-1 (the host material) and compound BD (the dopant material) are co-deposited at a ratio of 2% by mass to form the first light-emitting layer with a thickness of 5 nm.

[0393] On the first luminescent layer, compound BH-2 (host material) and compound BD (dopant material) are co-deposited at a ratio of 2% by mass to form a second luminescent layer with a film thickness of 20 nm.

[0394] On the second luminescent layer, compound ET-1 is deposited by vapor deposition to form the first electron transport layer with a thickness of 10 nm.

[0395] On the first electron transport layer, compound ET-2 is deposited by vapor deposition to form a second electron transport layer with a thickness of 15 nm.

[0396] LiF was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0397] Metallic Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0398] The component structure of the organic EL element in Example 1 is briefly shown below.

[0399] ITO(130) / HA(5) / HT-1(80) / HT-2(10) / Inv-1:BD(5:2%) / BH-2:BD(20:2%) / ET-1(10) / ET-2(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Additionally, the percentage numbers in parentheses indicate the proportion (by mass%) of the latter compound in that layer.

[0400] <Evaluation of Organic EL Components> External quantum efficiency (EQE) For the fabricated organic EL devices, to achieve a current density of 10 mA / cm² 2A voltage was applied to the organic EL element, and the EL emission spectrum was measured using a CS-2000 spectrophotometer (manufactured by Conicaminodesk Ltd.). The results are shown in Table 1.

[0401] Examples 2-6 As the main material for the light-emitting layer, the compounds described in Table 1 were used instead of Inv-1. Otherwise, organic EL elements were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 1. In Table 1, the element lifetime is expressed as a relative value with Comparative Example 1 as 100%.

[0402] Comparative Examples 1-3 As the main material for the light-emitting layer, the compounds described in Table 1 were used instead of Inv-1. Otherwise, organic EL elements were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 1. In Table 1, the element lifetime is expressed as a relative value with Comparative Example 1 as 100%.

[0403] [Table 1] .

[0404] <Compound Synthesis> The compounds synthesized in Examples 1-8 are shown below.

[0405] [Chemical 110] (Synthesis Example 1) Synthesis of Inv-1 Synthesize Inv-1 using the following synthesis path.

[0406] [Chemistry 111] Under an argon atmosphere, 1-iodotriphenylene (2.71 g, 7.65 mmol), intermediate 1 (2.05 g, 7.76 mmol), Pd2(dba)3 (140 mg, 0.153 mmol), SPhos (251 mg, 0.612 mmol), cesium carbonate (3.74 g, 11.48 mmol), 1,4-dioxane (40.8 mL), and water (10.2 mL) were added to a 200 mL three-necked flask and heated under reflux for 6 hours. The precipitated solid was filtered from the reaction mixture and washed with water and methanol. The dried brown solid was purified by silica gel chromatography and heavy crystallization to give 2.90 g of a white solid. The white solid was identified as Inv-1 (75% yield) by ASAP-MS analysis.

[0407] (Synthesis Example 2) Synthesis of Inv-2 Synthesize Inv-2 using the following synthesis path.

[0408] [Chemistry 112] Under an argon atmosphere, 1-iodotriphenylene (3.00 g, 8.47 mmol), intermediate 2 (4.64 g, 12.71 mmol), Pd2(dba)3 (155 mg, 0.169 mmol), SPhos (209 mg, 0.508 mmol), cesium carbonate (4.14 g, 12.71 mmol), 1,4-dioxane (33.9 mL), and water (8.47 mL) were added to a 200 mL three-necked flask, and the mixture was heated under reflux for 3.5 hours. The reaction solution was then allowed to cool, and intermediate 2 (3.09 g, 8.47 mmol) was added again, followed by heating under reflux for 3 hours. The reaction solution was cooled, and intermediate 2 (4.64 g, 12.71 mmol), Pd2(dba)3 (155 mg, 0.169 mmol), and SPhos (209 mg, 0.508 mmol) were added. The mixture was heated under reflux for 3 hours. The reaction solution was extracted with dichloromethane, and the collected organic phase was dried over magnesium sulfate and concentrated. The resulting brown oil was purified by silica gel chromatography and heavy crystallization to give 1.35 g of a white solid. The white solid was identified as Inv-2 (yield 35%) by ASAP-MS analysis.

[0409] (Synthesis Example 3) Synthesis of Inv-3 Synthesize Inv-3 using the following synthesis path.

[0410] [Chemistry 113] In the synthesis of Inv-1, intermediate 3 was used instead of intermediate 1, and the same procedure was performed to obtain 2.31 g of a white solid. Analysis by ASAP-MS identified it as Inv-3 (yield 69%).

[0411] (Synthesis Example 4) Synthesis of Inv-4 Synthesize Inv-4 using the following synthesis path.

[0412] [Chemistry 114] In the synthesis of Inv-1, intermediate 4 was used instead of intermediate 1, and the same procedure was performed to obtain 2.56 g of a white solid. Analysis by ASAP-MS identified it as Inv-4 (yield 78%).

[0413] (Synthesis Example 5) Synthesis of Inv-5 Synthesize Inv-5 using the following synthesis path.

[0414] [Chemistry 115] In the synthesis of Inv-1, intermediate 5 was used instead of intermediate 1, and the same procedure was followed to obtain 2.36 g of a white solid. Analysis by ASAP-MS identified it as Inv-5 (yield 72%).

[0415] (Synthesis Example 6) Synthesis of Inv-6 Synthesize Inv-6 using the following synthesis path.

[0416] [Chemistry 116] In the synthesis of Inv-1, intermediate 6 was used instead of intermediate 1, and the same procedure was performed to obtain 1.52 g of a white solid. Analysis by ASAP-MS identified it as Inv-6 (yield 45%).

[0417] (Synthesis Example 7) Synthesis of Inv-7 Synthesize Inv-7 using the following synthesis path.

[0418] [Chemistry 117] In the synthesis of Inv-1, intermediate 7 was used instead of intermediate 1, and the same procedure was followed to obtain 1.52 g of a white solid. Analysis by ASAP-MS identified it as Inv-7 (yield 45%). (Synthesis Example 8) Synthesis of Inv-8 Synthesize Inv-8 using the following synthesis path.

[0419] [Chemistry 118] .

[0420] Synthesis of Intermediate 10 Under an argon atmosphere, intermediates 8 (10.0 g, 36.6 mmol), 9 (6.07 g, 44.0 mmol), Pd2(dba)3 (671 mg, 0.733 mmol), SPhos (1.20 g, 2.93 mmol), sodium carbonate (11.7 g, 110 mmol), 1,2-dimethoxyethane (150 mL), and water (37 mL) were added to a 500 mL three-necked flask and heated under reflux for 4 hours. The reaction solution was extracted with dichloromethane, dried over magnesium sulfate, and concentrated. The resulting brown oil was purified by silica gel chromatography and heavy crystallization to give 6.13 g of a white solid. ASAP-MS analysis identified it as intermediate 10 (70% yield).

[0421] Synthesis of intermediate 11 Under an argon atmosphere, intermediate 10 (6.13 g, 25.6 mmol), dichloromethane (85 mL), and pyridine (3.1 mL, 38.5 mmol) were added to a 200 mL three-necked flask and cooled to 0 °C in an ice bath. Trifluoromethanesulfonic anhydride (5.1 mL, 30.8 mmol) was added dropwise, and the mixture was heated to room temperature with stirring for 4 hours. The reaction solution was quenched with ice water, extracted with dichloromethane, dried over magnesium sulfate, and concentrated. The resulting yellow oil was purified by silica gel chromatography and heavy crystallization to give 8.75 g of a white solid. ASAP-MS analysis identified it as intermediate 11 (yield 92%).

[0422] Synthesis of intermediate 13 Under an argon atmosphere, intermediates 11 (8.75 g, 23.6 mmol), 12 (3.94 g, 25.9 mmol), Pd2(dba)3 (432 mg, 0.371 mmol), SPhos (774 mg, 1.89 mmol), sodium carbonate (7.50 g, 70.7 mmol), 1,2-dimethoxyethane (95 mL), and water (24 mL) were added to a 500 mL three-necked flask and heated under reflux for 4 hours. The reaction solution was extracted with dichloromethane, dried over magnesium sulfate, and concentrated. The resulting brown oil was purified by silica gel chromatography and heavy crystallization to give 6.67 g of a white solid. ASAP-MS analysis identified it as intermediate 13 (yield 86%).

[0423] Synthesis of intermediate 14 Under an argon atmosphere, intermediate 13 (6.67 g, 20.3 mmol), dichlorobis(tricyclohexylphosphine)palladium (748 mg, 1.01 mmol), tert-valeric acid (724 mg, 7.09 mmol), cesium carbonate (13.2 g, 40.5 mmol), and dimethylacetamide (100 mL) were added to a 200 mL three-necked flask. The mixture was heated and stirred at 150 °C for 4 hours. The reaction solution was extracted with dichloromethane, washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The resulting brown solid was purified by silica gel chromatography and heavy crystallization to give 3.80 g of a white solid. ASAP-MS analysis identified it as intermediate 14 (64% yield). Synthesis of Intermediate 15 Under an argon atmosphere, intermediate 14 (3.80 g, 13.0 mmol) and dichloromethane (65 mL) were added to a 200 mL three-necked flask and cooled to 0 °C in an ice bath. 1 M boron tribromide (15.6 mL, 15.6 mmol) was added dropwise, and the mixture was heated to room temperature with stirring for 6 hours. The reaction solution was quenched with ice water, extracted with dichloromethane, dried over magnesium sulfate, and concentrated. The resulting brown solid was purified by silica gel chromatography and heavy crystallization to give 3.08 g of brown solid. ASAP-MS analysis identified it as intermediate 15 (yield 85%).

[0424] Synthesis of intermediate 16 Under an argon atmosphere, intermediate 15 (3.08 g, 11.1 mmol), dichloromethane (37 mL), and pyridine (1.34 mL, 16.6 mmol) were added to a 200 mL three-necked flask and cooled to 0 °C in an ice bath. Trifluoromethanesulfonic anhydride (2.18 mL, 13.3 mmol) was added dropwise, and the mixture was heated to room temperature with stirring for 4 hours. The reaction solution was quenched with ice water, extracted with dichloromethane, dried over magnesium sulfate, and concentrated. The resulting yellow solid was purified by silica gel chromatography and heavy crystallization to give 3.99 g of a white solid. ASAP-MS analysis identified it as intermediate 16 (yield 88%).

[0425] Synthesis of Inv-8 Under an argon atmosphere, intermediate 16 (2.00 g, 4.87 mmol), intermediate 17 (2.52 g, 10.2 mmol), Pd2(dba)3 (178 mg, 0.195 mmol), SPhos (320 mg, 0.779 mmol), cesium carbonate (11.7 g, 24.3 mmol), 1,2-dimethoxyethane (26 mL), and water (6.5 mL) were added to a 200 mL three-necked flask, and the mixture was heated under reflux for 4 hours. The precipitated solid was filtered off, washed with water and methanol, and dried. The resulting brown solid was purified by silica gel chromatography and heavy crystallization to give 1.33 g of a white solid. ASAP-MS analysis identified it as Inv-8 (yield 43%).

[0426] The foregoing has described several embodiments and / or examples of the present invention in detail. However, those skilled in the art will readily apply many changes to these illustrative embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, these many changes are also included within the scope of the present invention.

[0427] All the documents described in this specification and the contents of the application that form the basis of this application based on the priority of the Paris Convention are hereby incorporated into this application.

Claims

1. The compound represented by formula (1) below, [Chemistry 119] In equation (1), R1~R 11 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group, with 5 to 50 cyclic atoms, either substituted or unsubstituted. Ar1 is Substituted or unsubstituted pyrene, Substituted or unsubstituted benzo[anthracene], or Substituted or unsubstituted benzoxanthine group.

2. The compound according to claim 1, wherein, R1~R 11 Each independently hydrogen atom, Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

3. The compound according to claim 1 or 2, wherein, R1~R 11 Each independently hydrogen atom, Substituted or unsubstituted phenyl Substituted or unsubstituted naphthyl groups Replaced or unreplaced foetida Substituted or unsubstituted pyrene, Substituted or unsubstituted benzo[anthracene] Substituted or unsubstituted dibenzofluorenyl, Substituted or unsubstituted dibenzofuranyl, Substituted or unsubstituted naphthobenzofuranyl, or Substituted or unsubstituted benzoxanthine group.

4. The compound according to any one of claims 1 to 3, wherein, R1~R2, R5~R6, and R9~R 11 It is a hydrogen atom.

5. The compound according to any one of claims 1 to 4, wherein, R1~R 11 It is a hydrogen atom.

6. The compound according to any one of claims 1 to 5, wherein, The compound shown in formula (1) has at least one deuterium atom.

7. The compound according to any one of claims 1 to 6, wherein, Ar1 is a group selected from the following formulas (Ar-1) to (Ar-9). [Chemistry 120] [Chemistry 121] [Chemistry 122] In formula (Ar-1)~(Ar-9), * indicates a bond with the triphenylene skeleton in formula (1). R 101 ~R 110 R 201 ~R 212 and R 301 ~R 310 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 15 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

8. The compound according to claim 7, wherein, R 101 ~R 110 R 201 ~R 212 and R 301 ~R 310 Each independently constitutes a hydrogen atom, Substituted or unsubstituted phenyl, or Substituted or unsubstituted naphthyl groups.

9. The compound according to claim 7 or 8, wherein, R 101 ~R 110 R 201 ~R 212 and R 301 ~R 310 It is a hydrogen atom.

10. The compound according to any one of claims 1 to 9, wherein, The compound represented by formula (1) is any one of the compounds represented by formulas (1-1) to (1-6) below. [Chemistry 123] [Chemistry 124] In equations (1-1) to (1-6), R1 to R 11 As defined in equation (1) above, R 101 ~R 110 R 201 ~R 206 R 208 ~R 212 and R 301 ~R 310 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 15 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

11. The compound according to any one of claims 1 to 10, wherein, The compound represented by formula (1) is any one of the compounds represented by formulas (1-11) to (1-16) below. [Chemistry 125] [Chemistry 126] In equations (1-11) to (1-16), R3 to R4 and R7 to R8 are defined as in equation (1) above. R 106 ~R 109 R 212 R 304 R 308 ~R 309 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted Substituted or unsubstituted aryl groups with 6 to 15 cyclic carbon atoms, or A monovalent oxygen-containing heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

12. Organic electroluminescent elements, which have a cathode, anode, and One or more organic layers disposed between the aforementioned cathode and the aforementioned anode, At least one of the aforementioned organic layers contains the compound according to any one of claims 1 to 11.

13. The organic electroluminescent element according to claim 12, comprising an anode, a light-emitting layer and a cathode in sequence, wherein at least one organic layer of the light-emitting layer comprises the aforementioned compound.

14. The organic electroluminescent element according to claim 13, wherein, The aforementioned light-emitting layer comprises a first layer and a second layer from the anode side, and the aforementioned first layer comprises the aforementioned compound.

15. An electronic device comprising the organic electroluminescent element according to any one of claims 12 to 14.

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