Compound, organic electroluminescence element, and electronic device

Abstract

An object of the present application is to provide an organic EL element with higher performance. The present application provides a compound represented by formula (1).

Description

[0001] This application is a divisional application of Chinese application filed on November 19, 2025, with application number 202511702157.3 and entitled "Compounds, Organic Electroluminescent Elements and Electronic Devices". Technical Field

[0002] This invention relates to novel compounds, organic electroluminescent elements, and electronic devices. Background Technology

[0003] When a voltage is applied to an organic electroluminescent element (hereinafter referred to as an organic EL element), holes are injected into the light-emitting layer from the anode and electrons from the cathode, respectively. Subsequently, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0004] 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.

[0005] Patent document 1 discloses a compound with a specific structure for use in organic EL elements.

[0006] Existing technical documents Patent documents Patent Document 1: Japanese Patent Application Publication No. 2021-090050. Summary of the Invention

[0007] The problem that the invention aims to solve The purpose of this invention is to provide higher performance organic EL devices.

[0008] Methods for solving problems 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.

[0009] According to the present invention, the following compounds are provided.

[0010] 1. The compound shown in formula (1), [Chemistry 1] In equation (1), R1~R 10 Each can be independently a hydrogen atom or a substituent Q; From R1 to R 10 Two or more adjacent groups are not bonded to each other; n1 is an integer from 0 to 3; When n1 is 0, (L1)n1 It is a single bond; When n1 is 2 or 3, multiple L1s can be the same or different from each other; L1 is: single key, or substituted or unsubstituted cyclic arylene groups with 6 to 50 carbon atoms; Ar1 is: Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted; Ar2 is a group represented by the following formula (1A), (1B) or (1C); [Chemistry 2] In formulas (1A), (1B) and (1C), * denotes a bond with the benzene anthracene skeleton of formula (1); By R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 A group consisting of two or more adjacent elements Mutual bonding forms substituted or unsubstituted monocyclic rings. Mutual bonding forms substituted or unsubstituted fused rings, or They do not bond with each other; R that does not form the aforementioned single ring and the aforementioned fused ring A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Each can be independently a hydrogen atom or a substituent Q; The substituent Q is: 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 Halogen atom, cyano 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.

[0011] 2. An organic electroluminescent element, which has the following characteristics: cathode, anode, and One or more organic layers disposed between the aforementioned cathode and the aforementioned anode; At least one of the organic layers contains the compound described in section 1 above.

[0012] 3. An electronic device having the organic electroluminescent element described in 2. above.

[0013] Invention Effects According to the present invention, higher performance organic EL elements can be provided. Attached Figure Description

[0014] 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

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

[0016] 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.

[0017] In this specification, the number of cyclic carbon atoms refers to the number of carbon atoms in the atoms constituting the ring itself in a compound whose atoms are bonded together to form a cyclic structure (e.g., monocyclic compounds, fused-ring compounds, cross-linked 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.

[0018] Furthermore, when the benzene ring is substituted with a substituent such as an alkyl group, the number of carbon atoms of 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 the ring-forming process of a benzene ring with a substituted alkyl group is 6. Similarly, when the naphthalene ring is substituted with a substituent such as an alkyl group, the number of carbon atoms of 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 the ring-forming process of a naphthalene ring with a substituted alkyl group is 10.

[0019] 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, cross-linked 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. Furthermore, for example, hydrogen atoms bonded to the carbon atoms of the quinoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinoline ring. Therefore, the number of cyclic atoms in a quinoline ring bonded with hydrogen atoms or substituents is 10.

[0020] 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 the substituents. Here, "YY" is greater than "XX", where "XX" means an integer greater than 1 and "YY" means an integer greater than 2.

[0021] 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" means an integer greater than 1 and "YY" means an integer greater than 2.

[0022] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0023] In this specification, "unsubstituted" in the context of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0024] Furthermore, in this specification, the term "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, the term "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.

[0025] Substituents described in this specification The substituents described in this specification will be explained below.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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.

[0031] 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.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] • "Substituted or unsubstituted aryl groups" As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls (specific example group G1A) and substituted aryls (specific example group G1B) can be cited. (Here, the unsubstituted aryl refers to the case where the "substituted or unsubstituted aryl" is an "unsubstituted aryl", and the substituted aryl refers to the case where the "substituted or unsubstituted aryl" is a "substituted aryl".) In this specification, when "aryl" is mentioned alone, it includes both "unsubstituted aryl" and "substituted aryl".

[0036] "Substituted aryl" means that one or more hydrogen atoms of the "unsubstituted aryl" are replaced by substituents. As the "substituted aryl", examples include groups in which one or more hydrogen atoms of the "unsubstituted aryl" in the following specific example group G1A are replaced by substituents, and examples of the substituted aryl in the following specific example group G1B. 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 this specification also includes groups in which hydrogen atoms bonded to the carbon atoms of the aryl itself in the "substituted aryl" in the following specific example group G1B are further replaced by substituents, and groups in which hydrogen atoms of the substituents in the "substituted aryl" in the following specific example group G1B are further replaced by substituents.

[0037] ・Unsubstituted aryls (specific example group G1A): Phenyl, p - Biphenylyl, m - Biphenylyl, o - Biphenylyl, 4 - p - Terphenyl - yl, 3 - p - Terphenyl - yl, 2 - p - Terphenyl - yl, 4 - m - Terphenyl - yl, 3 - m - Terphenyl - yl, 2 - m - Terphenyl - yl, 4 - o - Terphenyl - yl, 3 - o - Terphenyl - yl, 2 - o - Terphenyl - yl, 1 - Naphthyl, 2 - Naphthyl, Anthryl, Benzoanthryl, Phenanthryl,[[ID=4​​​​​​​​​​​​​​​ Pentaphenyl, Fluorine 9,9'-spirodifluorene, benzo[f]fluorene, Dibenzofluorene, Fluoranthene group, 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).

[0038] [Chemistry 3] [Chemistry 4] .

[0039] • 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.

[0040] • "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.

[0041] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0042] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0043] 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). (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".

[0044] "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 the group in the "substituted heterocyclic group" of Specific Example Group G2B in which the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself are further replaced by substituents, and the group in the "substituted heterocyclic group" of Specific Example Group G2B in which the hydrogen atoms of the substituents are further replaced by substituents.

[0045] 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).

[0046] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group 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).

[0047] • 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, Pyrimidinyl, Pyrazinyl, Triazine group Indole, Isoindolyl, Indoleazine, Quinazine-based Quinoline, Isoquinoline, Crenoline group Phthaloazine Quinazolinyl, Quinoxaloyl, Benzimidazole group, Indazole group, phenanthroline, phenanthridine, acridine group, Phenolicazine Carbazolyl, Benzocarbazolyl, Morpholinyl group phenoxazine group, phenothiazine group, Azacarbazolyl and diazacarbazolyl.

[0048] • 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.

[0049] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3): Thiophene group Thiazole group, Isothiazolyl, Thiadiazole group, benzothienyl isobenzothienyl dibenzothienyl Naphthobenzothienyl Benzothiazolyl, Benzisothiazolyl, phenothiazine group, dinaphthothiophenyl azadibenzothienyl diazadibenzothienyl azanaphthobenzothienyl, and diazanaphthobenzothienyl.

[0050] • 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 5] [Chemistry 6] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y A Each 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.

[0051] 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.

[0052] • 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.

[0053] • 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].

[0054] • Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): Phenyl dibenzothiophene, Methyldibenzothiophene, tert-butyldibenzothiophene, and The monovalent residue of [9H-thioxanth-9,9'-[9H]fluorene].

[0055] • 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 hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH, and X A and Y A One of the hydrogen atoms in the methylene group when it is CH2 is one or more hydrogen atoms.

[0056] • "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".

[0057] "Substituted alkyl" means 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, "alkyl" in "unsubstituted alkyl" means a chain-like 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 a "substituted alkyl" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in a "substituted alkyl" of specific example group G3B are further replaced by substituents.

[0058] • Unsubstituted alkyl groups (specific example group G3A): methyl, Ethyl, n-propyl, Isopropyl, n-Butyl, Isobutyl, sec-butyl, and tert-butyl.

[0059] • Substituted alkyl groups (specific example group G3B): Heptafluoropropyl (including isomers) Pentafluoroethyl, 2,2,2-Trifluoroethyl, Trifluoromethyl

[0060] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" described in this specification (specific example group G4) include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B). (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."

[0061] "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.

[0062] • Unsubstituted alkenyl groups (specific example group G4A): vinyl, Allyl 1-Butenyl, 2-Butenyl, and 3-Butenyl.

[0063] • Substituted alkenyl groups (specific example group G4B): 1,3-Butadienyl, 1-Methylvinyl 1-Methylallyl, 1,1-Dimethylallyl, 2-Methylallyl, and 1,2-Dimethylallyl.

[0064] • "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".

[0065] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" group are replaced by substituents. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl" group (specific example group G5A) are replaced by substituents.

[0066] • Unsubstituted alkynyl group (specific example group G5A): Acetylene group.

[0067] • "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). (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".

[0068] "Substituted cycloalkyl" means 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.

[0069] • Unsubstituted cycloalkyl groups (specific example group G6A): Cyclopropyl Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Adamantyl, 2-Adamantyl, 1-Norbornel alkyl, and 2-Norbornel alkyl.

[0070] • Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl.

[0071] • "-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).

[0072] Here, G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0073] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0074] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0075] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0076] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.

[0077] In -Si(G1)(G2)(G2), multiple G2s may be identical or different from each other.

[0078] In -Si(G1)(G1)(G2), multiple G1s may be identical or different from each other.

[0079] In -Si(G2)(G2)(G2), multiple G2s may be identical or different from each other.

[0080] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.

[0081] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.

[0082] • "-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).

[0083] Here, G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0084] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0085] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0086] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0087] • "-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).

[0088] Here, G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0089] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0090] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0091] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0092] • "-N (R 906 (R) 907 The group shown in the figure” As described in this specification, -N(R) 906 (R) 907Specific 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).

[0093] Here, G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0094] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0095] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0096] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0097] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0098] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0099] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0100] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0101] • "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.

[0102] • "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 constituting the alkyl group is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group are replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group are replaced by substituents. It should be noted that "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 a "substituted fluoroalkyl" group are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group are further replaced by substituents. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the aforementioned "alkyl" (specific example group G3) are replaced by fluorine atoms.

[0103] • "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl" as used in this specification means a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group are replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" means a group in which one or more hydrogen atoms of a "haloalkyl" group 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 a "substituted haloalkyl" group are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group are further replaced by substituents. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms in the aforementioned "alkyl" (specific example group G3) are replaced by halogen atoms. Sometimes haloalkyl is referred to as alkyl halide.

[0104] • "Substituted or unsubstituted alkoxy groups" Specific examples of "substituted or unsubstituted alkoxy groups" described in this specification are groups represented by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0105] • "Substituted or unsubstituted alkyl thiols" Specific examples of "substituted or unsubstituted alkyl thio groups" described in this specification are groups represented by -S (G3), where G3 is the "substituted or unsubstituted alkyl" described in the specific example group G3. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkyl thio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0106] • "Substituted or unsubstituted aryloxy group" Specific examples of "substituted or unsubstituted aryloxy group" described in this specification are groups represented by -O (G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, 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.

[0107] • "Substituted or unsubstituted arylthio groups" Specific examples of "substituted or unsubstituted aryl thiogroup" described in this specification are groups represented by -S (G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of cyclic carbon atoms of the "unsubstituted aryl thiogroup" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0108] • "Substituted or unsubstituted trialkylsilyl groups" Specific examples of "trialkylsilyl" described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 refers to "substituted or unsubstituted alkyl" as described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0109] • "Substituted or unsubstituted aralkyl groups" Specific examples of "substituted or unsubstituted aralkyl" described in this specification are groups represented by -(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 an "alkyl" is replaced by an "aryl" as a substituent, and is one form of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" replaced by an "unsubstituted aryl", and the number of carbon atoms in the "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0110] 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.

[0111] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein 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.

[0112] 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.

[0113] In this specification, the carbazoyl group, unless otherwise specified herein, refers to any of the following groups.

[0114] [Chemistry 7] In this specification, (9-phenyl)carbazolyl refers to any of the following groups unless otherwise specified in this specification.

[0115] [Chemistry 8] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding site.

[0116] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any of the following groups unless otherwise specified in this specification.

[0117] [Chemistry 9] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * indicates the bonding site.

[0118] 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.

[0119] • "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.

[0120] • "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise stated, the "substituted or unsubstituted divalent heterocyclic group" described in this specification refers to 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.

[0121] • "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.

[0122] 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).

[0123] [Chemistry 10] [Chemistry 11] In the aforementioned general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0124] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * indicates the bonding site.

[0125] [Chemistry 12] In the aforementioned general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0126] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0127] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * indicates the bonding site.

[0128] [Chemistry 13] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0129] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * indicates the bonding site.

[0130] 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).

[0131] [Chemistry 14] [Chemistry 15] [Chemistry 16] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0132] [Chemistry 17] [Chemistry 18] [Chemistry 19] [Chemistry 20] In the aforementioned general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0133] The above is an explanation of the substituents described in this specification.

[0134] • "Cases where bonding forms rings" In this specification, the phrase "one or more groups of two or more adjacent units 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" means the following: "one or more groups of two or more adjacent units bonded together to form a substituted or unsubstituted monocyclic ring," "one or more groups of two or more adjacent units bonded together to form a substituted or unsubstituted fused ring," and "one or more groups of two or more adjacent units not bonded together."

[0135] The following description addresses the cases of "a monocyclic ring formed by the mutual bonding of one or more groups consisting of two or more adjacent elements" and "a fused ring formed by the mutual bonding of one or more groups consisting of two or more adjacent elements" (hereinafter, these cases are sometimes collectively referred to as "the cases of ring formation 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.

[0136] [Chemistry 21] 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 R927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0137] The phrase "one or more groups" means that two or more groups consisting of two or more adjacent elements can simultaneously form a loop. For example, R 921 With R 922 Mutual bonding forms a ring Q A And at the same time R 925 With R 926 Mutual bonding forms a ring Q B In the case of the above-mentioned general formula (TEMP-103), the anthracene compound is represented by the following general formula (TEMP-104).

[0138] [Chemistry 22] The case of rings formed by "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, it means R 921 With R 922 Mutual bonding forms a ring Q A And R 922 With R 923 Mutual bonding forms a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923 When the groups of components Q bond together to form a ring and fuse 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 .

[0139] [Chemistry 23] 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 "a group 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 BEach 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 C They fuse to form fused rings. The ring Q of the aforementioned general formula (TMEP-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 (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0140] "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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by 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 Meaning by 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 921With R 922 The resulting ring is a benzene ring.

[0145] 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.

[0146] 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.

[0147] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0148] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0149] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

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

[0151] Unless otherwise stated in this specification, the preferred form is an "unsaturated ring" consisting of "one or more groups of two or more adjacent atoms bonded together to form a substituted or unsubstituted monocyclic ring" or "a fused ring formed by mutual bonding".

[0152] 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 "Substituents Described in this Specification" section above.

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

[0154] The above explains the cases of "one or more groups consisting of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring" and "one or more groups consisting of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring" ("the case of bonded ring formation").

[0155] • 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] In this specification, the numerical range “AA~BB” means a range that includes the value AA, which precedes “AA~BB”, as the lower limit and the value BB, which follows “AA~BB”, as the upper limit.

[0163] [Novel Compounds] One embodiment of the compound of the present invention is shown in formula (1).

[0164] [Chemistry 24] In equation (1), R1~R 10 Each can be a hydrogen atom or a substituent Q. From R1 to R 10 Two or more adjacent groups are not bonded to each other. n1 is an integer from 0 to 3. When n1 is 0, (L1) n1 It is a single key. When n1 is 2 or 3, multiple L1s can be the same or different from each other. L1 is: single key, or A substituted or unsubstituted cyclic aryl group with 6 to 50 carbon atoms. Ar1 is: Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted. Ar2 is a group represented by formula (1A), (1B) or (1C) below. [Chemistry 25] In formulas (1A), (1B) and (1C), * denotes a bond with the benzene anthracene skeleton of formula (1). By R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 A group consisting of two or more adjacent elements Mutual bonding forms substituted or unsubstituted monocyclic rings. Mutual bonding forms substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the aforementioned single ring and the aforementioned fused ring A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Each can be a hydrogen atom or a substituent Q. The substituent Q is: 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 Halogen atom, cyano 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.

[0165] When the compounds of one aspect of the present invention are used in the organic layer of an organic EL element, they can improve the performance of the element. For example, organic EL elements with excellent colorimetry (CIE-x, CIE-y), high efficiency, and long lifetime can be achieved.

[0166] A wider color gamut for a display is important in expanding the range of colors that can be displayed and in expressing more natural and vibrant colors. According to a compound of one aspect of the present invention, it is possible to achieve an organic EL element that maintains the same level of chromaticity as conventional displays and is more efficient and has a longer lifespan compared to conventional displays.

[0167] CIE-x refers to the x-component of the CIE1931 chromaticity coordinates, and CIE-y refers to the y-component of the CIE1931 chromaticity coordinates.

[0168] The colorimetry, efficiency, and lifetime of the organic EL element were determined using the methods described in the examples.

[0169] One aspect of the present invention comprises a compound comprising a benzonaphthofuranyl (Ar2) of formula (1A), (1B) or (1C) bonded to the 12 position of the benzanthracene skeleton by a single bond, and it is believed that the above-mentioned effects can be obtained by adopting such a structure.

[0170] While the reasons for the above effect may not be clear, it is believed that by bonding the benzonaphthofuran skeleton to the 12-position of the benzanthracene skeleton at specific bonding positions (refer to formulas (1A), (1B) and (1C)), the two skeletons are stereotactically twisted into a large shape, and the intermolecular interaction is suppressed, thereby exhibiting the above effect.

[0171] In one implementation, R1 to R 10 It is a hydrogen atom.

[0172] In equation (1), n1 is an integer from 0 to 3.

[0173] When n1 is 0, (L1) n1 Ar1 is a single bond, and it is directly bonded to the benzene anthracene skeleton.

[0174] When n1 is 1, Ar1 is bonded to the benzanthracene skeleton via L1.

[0175] When n1 is 2 or 3, 2 or 3 L1s are connected in series. In this case, Ar1 and the benzenexane skeleton are bonded to the L1 that is furthest apart from each other in the series connection.

[0176] In one implementation, n1 is 0, 1, or 2.

[0177] In one implementation, n1 is 0 or 1.

[0178] In one implementation, n1 is 0.

[0179] In one embodiment, L1 is a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group.

[0180] In one implementation, L1 is a single bond.

[0181] In one embodiment, Ar1 is an unsubstituted phenyl, an unsubstituted biphenyl, or an unsubstituted naphthyl.

[0182] In one implementation, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Two or more adjacent groups are not bonded to each other.

[0183] In one implementation, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Each independently is: hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0184] In one implementation, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Each independently is: hydrogen atom, or Aryl groups with 6 to 18 cyclic carbon atoms, either substituted or unsubstituted.

[0185] In one implementation, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19Each is independently a hydrogen atom, an unsubstituted phenyl group, an unsubstituted biphenyl group, or an unsubstituted naphthyl group.

[0186] In one implementation, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 It is a hydrogen atom.

[0187] In one implementation, R A15 R A18 R B17 Or R C12 To replace the base Q.

[0188] In one embodiment, the substituent Q is an alkyl group with 1 to 50 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[0189] In one embodiment, the substituent Q is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[0190] In one embodiment, the substituent Q is an aryl group with 6 to 18 cyclic carbon atoms, either substituted or unsubstituted.

[0191] In one embodiment, the substituent Q is an unsubstituted phenyl, an unsubstituted biphenyl, or an unsubstituted naphthyl.

[0192] In one embodiment, the compound represented by formula (1) is shown in formula (1-1), (1-2), or (1-3) below.

[0193] [Chemistry 26] In equations (1-1) to (1-3), R1 to R 10 Ar1, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 As defined in equation (1) above.

[0194] In one embodiment, the compound represented by formula (1) is represented by any of the following formulas (1-11) to (1-31).

[0195] [Chemistry 27] In equations (1-11) to (1-31), Ar1 and R A12 ~R A13 R A15 ~RA18 R B12 ~R B17 R C12 ~R C13 and R C16 ~R C19 As defined in equation (1) above.

[0196] In one embodiment, the compound represented by formula (1) is shown in formula (1-11) or (1-21) below.

[0197] [Chemistry 28] In equations (1-11) to (1-21), Ar1 and R A12 ~R A13 R A15 ~R A18 and R B12 ~R B17 As defined in equation (1) above.

[0198] In one embodiment, the compound represented by formula (1) has at least one deuterium atom.

[0199] In one embodiment, R1 to R1 are hydrogen atoms. 10 At least one of them is a deuterium atom.

[0200] In one implementation, R1 to R 10 It is a deuterium atom.

[0201] In one implementation, R1 to R 10 It is a protium atom.

[0202] In one implementation, Ar1 has at least one deuterium atom.

[0203] In one embodiment, Ar1 has all its hydrogen atoms as deuterium atoms.

[0204] In one embodiment, Ar1 has all its hydrogen atoms as protium atoms.

[0205] In one implementation, Ar2 has at least one deuterium atom.

[0206] In one implementation, Ar2 has all its hydrogen atoms as deuterium atoms.

[0207] In one embodiment, Ar2 has all its hydrogen atoms as protium atoms.

[0208] In one embodiment, R is a hydrogen atom A11 ~R A19 R B11 ~R B19 and RC11 ~R C19 At least one of them is a protium atom.

[0209] In one embodiment, R is a hydrogen atom A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 It is a protium atom.

[0210] In one embodiment, R is a hydrogen atom A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 At least one of them is a deuterium atom.

[0211] In one embodiment, R is a hydrogen atom A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 It is a deuterium atom.

[0212] In one embodiment, the substituent Q has at least one deuterium atom.

[0213] In one embodiment, the substituent Q has all its hydrogen atoms as deuterium atoms.

[0214] In this specification, the term "having deuterium atoms" means that, for at least one hydrogen atom in the compound or group, the proportion of deuterium atoms is greater than that found naturally, relative to the total number of protium and deuterium atoms.

[0215] In this specification, a specific hydrogen atom (or R as a hydrogen atom) is referred to as... x (X is an integer used for this specific substituent) "for deuterium" means that in this hydrogen atom, the proportion of deuterium atoms is greater than that naturally occurring relative to the total number of protium and deuterium atoms.

[0216] 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.

[0217] 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 for a specific substituent) means that in this hydrogen atom, the proportion of deuterium atoms relative to the total number of protium atoms and deuterium atoms is as follows, which is naturally occurring.

[0218] 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.

[0219] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) is: Alkyl groups with 1 to 50 carbon atoms alkenyl groups with 2 to 50 carbon atoms Alkyne groups 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.

[0220] 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 monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0221] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) 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.

[0222] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) 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.

[0223] The compounds of one embodiment of the present invention can be synthesized, according to the examples, by using known alternative reactions and starting materials corresponding to the target.

[0224] The following describes specific examples of compounds according to one aspect of the present invention, but these are merely illustrative examples, and the compounds according to one aspect of the present invention are not limited to the specific examples described below.

[0225] [Chemistry 29] [Chemistry 30] [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] [Chemistry 73] [Chemistry 74] [Chemistry 75] [Chemistry 76] [Chemistry 77] [Chemistry 78] [Chemistry 79] [Chemistry 80] [Chemistry 81] [Chemistry 82] [Chemistry 83] [Chemistry 84] [Chemistry 85] [Chemistry 86] [Chemistry 87] [Chemistry 88] [Chemistry 89] [Chemistry 90] [Chemistry 91] [Chemistry 92] [Chemistry 93] [Chemistry 94] [Chemistry 95] [Chemistry 96] [Chemistry 97] [Chem. 98] [Chemistry 99] [Chemistry 100] [Chemistry 101] [Chemistry 102] [Chemistry 103] [Chemistry 104] [Chemistry 105] [Chemistry 106] [Chemistry 107] [Chemistry 108] [Chemistry 109] [Chemical 110] [Chemistry 111] [Chemistry 112] [Chemistry 113] [Chemistry 114] [Chemistry 115] [Chemistry 116] [Chemistry 117] [Chemistry 118] [Chemistry 119] [Chemistry 120] [Chemistry 121] [Chemistry 122] [Chemistry 123] [Chemistry 124] [Chemistry 125] [Chemistry 126] [Chemistry 127] [Chemistry 128] [Chemistry 129] [Chemistry 130] [Chemistry 131] [Chemistry 132] [Chemistry 133] [Chemistry 134] [Chemistry 135] [Chemistry 136] [Chemistry 137] [Chemistry 138] [Chemistry 139] [Chemistry 140]

[0226] Materials for organic electroluminescent devices One aspect of the compound of the present invention is used as a material for organic EL elements, for example, as a material used in the light-emitting layer of organic EL elements.

[0227] [Organic EL element] An organic EL element according to one aspect of the present invention will be described.

[0228] An organic EL element of one aspect of the present invention has: a cathode, an anode, and one or more organic layers disposed between the cathode and the anode; at least one of the organic layers contains a compound of one aspect of the present invention (a compound represented by formula (1)).

[0229] An organic EL element of one aspect of the present invention can improve performance by having the above-described configuration.

[0230] In one embodiment, the light source comprises an anode, a light-emitting layer, and a cathode in sequence, wherein at least one organic layer in the light-emitting layer comprises a compound of one aspect of the present invention.

[0231] 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 of one aspect of the present invention.

[0232] In one embodiment, in an organic EL element of one aspect of the present invention, the light-emitting layer further comprises a compound represented by any one of the following formulas (D11) to (D41).

[0233] [Chemistry 141] Equations (D11) to (D41) are described below.

[0234] (The compound represented by formula (D11)) The compound represented by formula (D11) will be described.

[0235] [Chemistry 142] In formula (D11), Each of the three Zs is an independent CR a Or nitrogen atoms. Rings A1 and A2 are 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.

[0236] 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. Mutual bonding forms substituted or unsubstituted monocyclic rings. Mutual bonding forms substituted or unsubstituted fused rings, or They do not bond with each other.

[0237] nD11 and nD12 are each independently 0, 1, 2, 3 or 4. 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. Mutual bonding forms substituted or unsubstituted monocyclic rings. Mutual bonding forms substituted or unsubstituted fused rings, or They do not bond with each other. R c When there are multiple R, it is composed of multiple R c One or more groups consisting of two or more adjacent elements. Mutual bonding forms substituted or unsubstituted monocyclic rings. Mutual bonding forms substituted or unsubstituted fused rings, or They do not bond with each other. R that does not form the aforementioned single ring and the aforementioned fused ring a R b and R c Each independently is: 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, either substituted or unsubstituted.

[0238] R 901 ~R 907 As defined in equation (1) above.

[0239] The aromatic hydrocarbon rings of A1 and A2 have the same structure as the compounds formed by introducing hydrogen atoms into the aryl groups with 6 to 50 carbon atoms mentioned above.

[0240] The "aromatic hydrocarbon rings" of A1 and A2 contain two carbon atoms on the fused bicyclic structure at the center of the aforementioned formula (D11) as cyclic atoms.

[0241] As a specific example of "aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms", compounds formed by introducing hydrogen atoms into "substituted or unsubstituted aryl groups" as described in Specific Example Group G1 can be cited.

[0242] The "heterocyclic rings" of A1 and A2 have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic groups with 5 to 50 cyclic atoms".

[0243] The "heterocyclic" rings A1 and A2 contain two carbon atoms on the fused bicyclic structure at the center of the aforementioned formula (D11) as cyclic atoms.

[0244] As a specific example of "a heterocycle with 5 to 50 cyclic atoms, whether substituted or unsubstituted", compounds formed by introducing hydrogen atoms into a "substituted or unsubstituted heterocyclic group" as described in Specific Example Group G2 can be cited.

[0245] Rb bonds to any of the carbon atoms that form an aromatic hydrocarbon ring as an Al ring, or to any of the atoms that form a heterocycle as an Al ring.

[0246] Rc bonds to any of the carbon atoms that form an aromatic hydrocarbon ring as an A2 ring, or to any of the atoms that form a heterocycle as an A2 ring.

[0247] In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D11a).

[0248] In one embodiment, at least two of Ra, Rb, and Rc are groups represented by the following formula (D11a).

[0249] [Chemistry 143] 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.

[0250] 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).

[0251] [Chemistry 144] In formula (D11b), L D102 and L D103 Each independently is: 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.

[0252] By Ar D102 and Ar D103 Groups Mutual bonding forms substituted or unsubstituted monocyclic rings. Mutual bonding forms substituted or unsubstituted fused rings, or They do not bond with each other.

[0253] Ar does not form the aforementioned monocyclic or fused ring D102 and Ar D103 Each independently is: 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.

[0254] The following are specific examples of compounds represented by formula (D11), but they are only examples and the compounds represented by formula (D11) are not limited to the specific examples described below.

[0255] [Chemistry 145] (The compound represented by formula (D21)) The compound represented by formula (D21) will be described.

[0256] [Chemistry 146] In equation (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).

[0257] R D205 With R D206 R D206 With R D207 and R D207 With R D208 At least one group of them are bonded to each other to form a divalent group as shown in the following formula (D23).

[0258] [Chemistry 147] R D211 ~R D214 R, and R that does not form 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).

[0259] R D221 ~R D224 R, and R that does not form 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).

[0260] X D2 It is an oxygen atom, a sulfur atom, or NR. D209 .

[0261] 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 is: 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, either substituted or unsubstituted.

[0262] [Chemistry 148] In formula (D24), Ar D201 and Ar D202 Each independently is: 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.

[0263] L D201 ~L D203 Each independently is: 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 linker formed by bonding 2 to 4 groups selected from substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms and substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms. * indicates the bonding position with the ring structure shown in formula (D21), or the group shown in formula (D22) or formula (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 (D23) are not particularly limited and can be in R. D201 ~R D208 The group can be formed at any of the possible positions. In addition to the compounds described in International Publication No. 2014 / 104144, other compounds shown below may be cited as examples of compounds represented by formula (D21), but these are merely examples and the compounds represented by formula (21) are not limited to the following specific examples.

[0266] [Chemistry 149] (The compound represented by formula (D31)) The compound represented by formula (D31) will be described.

[0267] [Chemistry 150] In equation (D31), By R D301 ~R D307 and R D311 ~R D317 Two or more adjacent rings may form a group of substituted or unsubstituted monocyclic rings, or may form substituted or unsubstituted fused rings, or may not be bonded to each other.

[0268] R that does not form the aforementioned single ring and the aforementioned fused ring D301 ~R D307 and R D311 ~R D317 Each independently is: 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.

[0269] R D321 and R D322Each independently is: 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.

[0270] R 901 ~R 907 As defined in equation (1) above. "By R" D301 ~R D307 and R D311 ~R D317 A group consisting of two or more adjacent elements, for example, R. D301 and R D302 The group composed of R D302 and R D303 The group composed of R D303 and R D304 The group composed of R D305 and R D306 The group composed of R D306 and R D307 The group composed of R D301 R D302 and R D303 A combination of groups, etc. In one implementation, R D301 ~R D307 and R D311 ~R D317 At least one of them is -N(R) 906 (R) 907 ).

[0273] In one implementation, RD301 ~R D307 and R D311 ~R D317 Two of them are -N (R) 906 (R) 907 ). In one implementation, R D301 ~R D307 and R D311 ~R D317 Each independently is: hydrogen atom, 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.

[0275] The following are specific examples of compounds represented by formula (D31), but they are only examples and the compounds represented by formula (D31) are not limited to the specific examples described below.

[0276] [Chemistry 151] [Chemistry 152]

[0277] (The compound represented by formula (D41)) The compound represented by formula (D41) will be described.

[0278] [Chemistry 153] In equation (D41), Rings a, b, and c are each independent of: Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0279] 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 they do not bond at all.

[0280] R that does not form the aforementioned heterocycle D401 and R D402 Each independently is: 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.

[0281] Rings a, b, and c are rings fused with a fused bicyclic structure at the center of formula (D41), which consists 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 heterocyclic ring with 5 to 50 cyclic atoms).

[0282] The aromatic hydrocarbon rings of rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aryl group described above. The aromatic hydrocarbon ring of ring a includes three carbon atoms in the fused bicyclic 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 bicyclic 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 formed by introducing hydrogen atoms into the aryl group as described in specific example group G1.

[0283] The "heterocycles" of rings a, b, and c have the same structure as compounds formed by introducing hydrogen atoms into the aforementioned "heterocyclic group". The "heterocycle" of ring a includes the three carbon atoms in the fused bicyclic structure at the center of formula (D41) as cyclizing atoms. The "heterocycles" of rings b and c include the two carbon atoms in the fused bicyclic structure at the center of formula (D41) as cyclizing atoms. Specific examples of "heterocycles with 5 to 50 substituted or unsubstituted cyclizing atoms" include compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in specific example group G2.

[0284] R D401 and R D402 Each 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 on the fused bicyclic structure at the center of formula (D41). The heterocycle in this case can also contain heteroatoms other than the nitrogen atom. R D401 and R D402 Bonding to ring a, b, or c specifically means that the atoms constituting ring a, b, or c bond with the atoms constituting ring R. D401 and R D402 Atomic bonding. For example, R D401 It can bond with the α ring to form a ring containing R D401 A nitrogen-containing heterocycle formed by the fusion of a ring and an a ring, consisting of a bicyclic fusion (or a fusion of three or more rings). Specific examples of such nitrogen-containing heterocycles include compounds corresponding to bicyclic fusion or more heterocyclic groups containing nitrogen, as described in Specific Example Group G2.

[0285] R D401 Cases involving b-ring bonding, R D402 The case of α-ring bonding, and R D402 The situation regarding bonding with the c-ring is the same as described above.

[0286] 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.

[0287] In one embodiment, rings a, b, and c in formula (D41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0288] 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.

[0289] In one embodiment, the compound represented by formula (D41) is the compound represented by formula (D42) below.

[0290] [Chemistry 154] In equation (D42), R D401A With selection from R D411 and R D421 One or more bonds in R form a substituted or unsubstituted heterocycle, or no bond at all. D402A With selection from R D413 and R D414 One or more bonds in the ring form a substituted or unsubstituted heterocycle, or no bond at all.

[0291] R does not form the aforementioned substituted or unsubstituted heterocycles D401A and R D402A Each independently is: 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.

[0292] R D411 ~R D421Two or more adjacent rings in a group are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other.

[0293] 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 is: 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.

[0294] R 901 ~R 907 As defined in equation (1) above.

[0295] R in equation (D42) D401A and R D402A R is the same as in equation (D41) D401 and R D402 The corresponding functional group.

[0296] For example, R D401A With R D411 These can be bonded to form bicyclic fused (or fused with three or more rings) nitrogen-containing heterocycles. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to bicyclic fused or more nitrogen-containing heterocyclic groups in Specific Example Group G2. R D401A With R D412 Bonding situation, R D402A With R D413 The bonding situation and R D402A With R D414 The bonding situation is the same as described above.

[0297] 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 bond together to form structures with benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings, etc., on the 6-membered rings they are bonded to. The resulting fused rings are naphthyl rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.

[0298] In one implementation, R does not contribute to 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.

[0299] In one implementation, R does not contribute to cyclic formation. D411 ~R D421 Each 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.

[0300] In one implementation, R does not contribute to cyclic formation. D411 ~R D421 Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms.

[0301] In one implementation, R does not contribute to 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.

[0302] In one embodiment, the compound represented by the aforementioned formula (D42) is the compound represented by the following formula (D43).

[0303] [Chemistry 155] In equation (D43), R D431 With R D446 Bonding forms substituted or unsubstituted heterocycles, or no bonding occurs. R D433 With R D447 Bonding forms substituted or unsubstituted heterocycles, or no bonding occurs. R D434 With RD451 Bonding forms substituted or unsubstituted heterocycles, or no bonding occurs. R D441 With R D442 Bonding forms substituted or unsubstituted heterocycles, or no bonding at all.

[0304] R D431 ~R D451 Two or more adjacent rings in a group are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other.

[0305] R does not form the aforementioned substituted or unsubstituted heterocycles or the aforementioned substituted or unsubstituted saturated or unsaturated rings. D431 ~R D451 Each independently is: 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.

[0306] R 901 ~R 907 As defined in equation (1) above.

[0307] R D431 Can be used with R D446 Bonding forms substituted or unsubstituted heterocycles. For example, R D431 With R D446 It can bond to form R D446所键合的 A nitrogen-containing heterocycle consisting of a benzene ring, a ring containing nitrogen, and a benzene ring corresponding to the a ring, fused together to form a triple-ring or higher nitrogen-containing heterocycle. Specific examples of such a nitrogen-containing heterocycle include compounds corresponding to triple-ring or higher nitrogen-containing heterocyclic groups in specific example group G2. R D433 With R D447 Bonding situation, RD434 With R D451 The bonding situation and R D441 and R D442 The bonding situation is the same as described above.

[0308] In one implementation, R does not contribute to cyclic formation. D431 ~R D451 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.

[0309] In one implementation, R does not contribute to cyclic formation. D431 ~R D451 Each 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.

[0310] In one implementation, R does not contribute to cyclic formation. D431 ~R D451 Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms.

[0311] In one implementation, R does not contribute to cyclic formation. D431 ~R D451 Each is an alkyl group consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms; R D431 ~R D451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0312] In one embodiment, the compound represented by the aforementioned formula (D43) is the compound represented by the following formula (D43A).

[0313] [Chemistry 156] In formula (D43A), R D461 for: 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, or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0314] R D462 ~RD465 Each independently is: 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, or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0315] In one implementation, R D461 ~R D465 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.

[0316] In one implementation, R D461 ~R D465 Each is an alkyl group, with 1 to 50 carbon atoms, whether substituted or unsubstituted.

[0317] In one embodiment, the compound represented by the aforementioned formula (D43) is the compound represented by the following formula (D43B).

[0318] [Chemistry 157] In formula (D43B), R D471 and R D472 Each independently is: 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 -N(R) 906 (R) 907 ),or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0319] R D473 ~R D475 Each independently is: 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 -N(R) 906 (R) 907 ),or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0320] R 906 and R 907 As defined in equation (1) above.

[0321] In one embodiment, the compound represented by the aforementioned formula (D43) is the compound represented by the following formula (D43B').

[0322] [Chemistry 158] In formula (D43B'), R D472 ~R D475 As defined in the aforementioned formula (D43B).

[0323] In one implementation, R D471 ~R D475 At least one of them is: 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 -N(R) 906 (R) 907 ),or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0324] In one implementation, R D472 for: hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted -N(R) 906 (R) 907 ),or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted. R D471 and R D473 ~R D475 Each independently is: Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted -N(R) 906 (R) 907 ),or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0325] In one embodiment, the compound represented by the aforementioned formula (D43) is the compound represented by the following formula (D43C).

[0326] [Chemistry 159] In formula (D43C), R D481 and R D482 Each independently is: 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, or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0327] R D483 ~R D486 Each independently is: 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, or Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0328] In one embodiment, the compound represented by the aforementioned formula (D43) is a compound represented by the following formula (D43C').

[0329] [Chemistry 160] In formula (D43C'), R D483 ~R D486 As defined in the aforementioned formula (D43C).

[0330] In one implementation, R D481 ~R D486 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.

[0331] In one implementation, R D481 ~R D486 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 cyclic carbon atoms.

[0332] In one embodiment, the compound represented by the aforementioned formula (D41) is the compound represented by the following formula (D44).

[0333] [Chemistry 161] In equation (D44), X D401 It can be O or S.

[0334] R D401B With selection from R D487 and R D497 One or more bonds in R form a substituted or unsubstituted heterocycle, or no bond at all. D402B With selection from R D489 and R D490 One or more bonds in the ring form a substituted or unsubstituted heterocycle, or no bond at all.

[0335] R does not form the aforementioned substituted or unsubstituted heterocycles D401B and R D402B Each independently is: 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.

[0336] R D487 ~R D497 Two or more adjacent rings in a group are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other.

[0337] 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 is: 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.

[0338] R 901 ~R 907 As defined in equation (1) above.

[0339] 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.

[0340] 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.

[0341] The compound shown in formula (D41) can be produced by first connecting the a ring, b ring, and c ring with a linker (containing NR). D401 Groups and containing NR D402 The intermediate is produced by bonding the a, b, and c rings together with a linker group (containing a group of B) (reaction 1), and the final product is produced by bonding the a, b, and c rings together with a linker group (containing a group of B) (reaction 2). In reaction 1, amination reactions such as the Buchwald–Hartwig reaction can be applied. In reaction 2, tandem hetero-Friedel-Crafts reactions can be applied.

[0342] The following are specific examples of compounds represented by formula (D41), but they are only examples and the compounds represented by formula (D41) are not limited to the specific examples described below.

[0343] [Chemistry 162] [Chemistry 163] [Chemistry 164] [Chemistry 165] [Chemistry 166] [Chemistry 167] [Chemistry 168] [Chemistry 169] [Chemistry 170] [Chemistry 171] [Chemistry 172] [Chemistry 173] [Chemistry 174] In addition to the compounds shown in formulas (D11), (D21), (D31) or (D41) above, the aforementioned light-emitting layer may also use compounds such as those shown below.

[0344] [Chemistry 175] In one embodiment, the aforementioned light-emitting layer contains a compound represented by formula (D31) or (D41) above.

[0345] In one embodiment, the aforementioned light-emitting layer contains a compound represented by the formula (D31) above.

[0346] In one embodiment, an organic EL element of the present invention has a hole transport region between the aforementioned anode and the aforementioned light-emitting layer.

[0347] In one embodiment, an organic EL element of the present invention has an electron transport region between the aforementioned cathode and the aforementioned light-emitting layer.

[0348] Reference Figure 1 This describes a schematic configuration of an organic EL element according to one aspect of the present invention.

[0349] An organic EL element 1 according to one embodiment of the present invention has: 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.

[0350] 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.

[0351] (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.) The hole transport region is a collective term for one or more layers disposed between the anode and the light-emitting layer. For example, starting 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 them, or it can be composed of only a portion of them. Furthermore, two or more types of layers can be used for each of the above layers; for example, two different hole transport layers can be stacked together.

[0352] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0353] 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 them, or it can be composed of only a portion of them. Furthermore, two or more types of layers can be used for each of the above layers; for example, two different electron transport layers can be stacked together.

[0354] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0355] The following describes the components that can be used in an organic EL element according to one aspect of the present invention, as well as the materials constituting each layer.

[0356] (Emitting layer) In one embodiment, the light-emitting layer comprises a compound of one aspect of the present invention (the compound shown in formula (1)).

[0357] In one embodiment, the light-emitting layer contains a compound of one aspect of the present invention and a compound represented by any of the aforementioned formulas (D11) to (D41).

[0358] In one embodiment, the light-emitting layer comprises a compound of one aspect of the present invention as the host material (sometimes also referred to as the matrix material).

[0359] In one embodiment, the light-emitting layer further comprises a dopant material.

[0360] In one embodiment, the light-emitting layer comprises a compound represented by any of the aforementioned formulas (D11) to (D41) as a dopant material (sometimes also referred to as a guest material, emitter, or light-emitting material).

[0361] In one embodiment, the light-emitting layer contains more than 1.1% by mass, 1.2% by mass, or 1.5% by mass of dopant material by total mass of the light-emitting layer.

[0362] In one embodiment, the light-emitting layer contains dopant material of 10% or less, 7% or less, or 5% or less of the total mass of the light-emitting layer.

[0363] In one embodiment, the light-emitting layer contains 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the total mass of the light-emitting layer as body material.

[0364] In one embodiment, the light-emitting layer contains less than 99% by mass of the host material of the total mass of the light-emitting layer.

[0365] The light-emitting layer may contain materials other than the host material and dopant material.

[0366] In one embodiment, the light-emitting layer comprises only the host material and the dopant material, or substantially only the host material and the dopant material. In the latter case, it may contain unavoidable impurities.

[0367] In one embodiment, the light-emitting layer comprises 80% or more, 85% or more, 90% or more, 95% or more, 99% or more, 99.5% or more, 99.9% or more, 99.99% or more, or 100% or more of the main material and dopant material.

[0368] The light-emitting layer may contain only one host material or two or more. The light-emitting layer may contain only one dopant material or two or more.

[0369] The luminescent layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as a highly luminescent substance, in addition to the compounds shown in any of the formulas (D11) to (D41) above, fluorescent compounds and phosphorescent compounds can be used. 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.

[0370] 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.

[0371] 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.

[0372] As the luminescent layer, it can be configured such that the highly luminescent substance (guest material) is dispersed in other substances (host material). As the substance used to disperse the highly luminescent substance, in addition to the material used in the present invention described above (a compound of one aspect of the present invention), various substances can be used, 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.

[0373] 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.

[0374] Alternatively, delayed fluorescence (thermally activated delayed fluorescence) compounds can 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.

[0375] In addition to the materials used in this invention as described above, the light-emitting layer may or may not contain substances other than those described above.

[0376] (Level 2) In one embodiment, the light-emitting layer comprises a first layer and a second layer, the first layer comprising a compound of one aspect of the present invention (the compound shown in formula (1)), and the second layer comprising at least one compound different from the first layer.

[0377] For the first layer, the content described above for the light-emitting layer can be applied.

[0378] In one embodiment, the second layer comprises a host material (second host material). As the host material, substances exemplified as host materials for the aforementioned light-emitting layer can be used.

[0379] In one embodiment, the second host material is a compound different from the host material (first host material) contained in the first layer.

[0380] Alternatively, a delayed fluorescence (thermally activated delayed fluorescence) compound can be used as the host material. The second layer may also contain a compound of one aspect of the present invention described above and a delayed fluorescence host compound.

[0381] In one embodiment, the second layer further comprises a dopant material (second dopant material). As the dopant material, substances exemplified as dopant materials for the aforementioned light-emitting layer can be used.

[0382] In one embodiment, the second dopant material is a compound represented by any of the formulas (D11) to (D41) above.

[0383] In one embodiment, the second dopant material is a compound different from the dopant material (first dopant material) contained in the first layer.

[0384] In one embodiment, the second dopant material is the same compound as the first dopant material.

[0385] In one embodiment, the second layer contains more than 1.1% by mass, more than 1.2% by mass, or more than 1.5% by mass of the total mass of the second layer.

[0386] 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.

[0387] 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 by mass of the total mass of the second layer.

[0388] In one embodiment, the second layer contains less than 99% by mass of the main material of the second layer.

[0389] The second layer may contain materials other than the host material and dopant materials.

[0390] In one implementation, the second layer comprises only the host material and dopant material, or substantially only the host material and dopant material. In the latter case, it may contain unavoidable impurities.

[0391] In one embodiment, the second layer comprises 80% or more, 85% or more, 90% or more, 95% or more, 99% or more, 99.5% or more, 99.9% or more, 99.99% or more, or 100% or more of the main material and dopant material.

[0392] The second layer can contain only one host material or two or more. The second layer can contain only one dopant material or two or more.

[0393] The second layer can be a fluorescent luminescent layer or a phosphorescent luminescent layer.

[0394] In one embodiment, the second layer is a fluorescent light-emitting layer.

[0395] (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.

[0396] (anode) The anode formed on the substrate preferably uses 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).

[0397] (hole injection layer) A hole injection layer is a layer containing a substance with high hole injection capacity. Substances with high hole injection capacity 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.).

[0398] (Hole transport layer) The hole transport layer is a layer containing substances with high hole transport properties. 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. Among these, any substance whose hole transport properties are higher than its electron transport properties can be used. It should be noted that the layer containing the substance with high hole transport properties can be not only a single layer, but also a layer formed by stacking two or more layers containing the above-mentioned substances.

[0399] (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.

[0400] 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.

[0401] (Electron transport layer) The electron transport layer is a layer containing substances with high electron transport capacity. The electron transport layer can use: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, aziridine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymeric compounds.

[0402] (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 8-hydroxyquinoline-lithium (Liq), as well as lithium oxide (LiO), can be used in the electron-injection layer. x Alkali metals, alkaline earth metals, or their compounds, etc.

[0403] (cathode) The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (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.

[0404] In one aspect of the organic EL element of the present invention, 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 level, and achieve good luminous efficiency, the thickness is usually preferred to be in the range of several nm to 1 μm.

[0405] In one embodiment of the organic EL element of the present invention, the method for forming each layer is not particularly limited. Conventionally known formation methods based on vacuum evaporation, spin coating, etc., 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.

[0406] [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.

[0407] 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

[0408] <Compound> The compounds of formula (1) used in the manufacture of the organic EL elements in Examples 1 to 12 are shown below.

[0409] [Chemistry 176] [Chemistry 177] The comparative example compounds used in the manufacture of the organic EL elements of Comparative Examples 1-4 and 6-8 are shown below.

[0410] [Chemistry 178] [Chemistry 179] The structures of other compounds used in the manufacture of the organic EL elements of Examples 1-12 and Comparative Examples 1-8 are described below.

[0411] [Chemistry 180] [Chemistry 181] Example 1 <Fabrication of Organic EL Components> Organic EL elements are fabricated as described below.

[0412] 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 isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. This resulted in an ITO film thickness of 130nm.

[0413] 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.

[0414] Compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[0415] Compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[0416] On the second hole transport layer, BH1-1 (the first host material) and compound BD-1 (the first dopant material) are co-deposited at a ratio of 2% by mass to form a first light-emitting layer with a film thickness of 5 nm.

[0417] On the first luminescent layer, compound BH-2 (the second host material) and compound BD-1 (the second dopant material) are co-deposited in a manner that the proportion of compound BD-1 reaches 2% by mass, forming a second luminescent layer with a film thickness of 20 nm.

[0418] Compound ET-1 was deposited on the second luminescent layer to form the first electron transport layer with a thickness of 10 nm.

[0419] Compound ET-2 was deposited on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm.

[0420] LiF was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0421] Metallic Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0422] The component structure of the organic EL element in Example 1 is briefly shown below.

[0423] ITO(130) / HA(5) / HT-1(80) / HT-2(10) / BH1-1:BD-1(5:2%) / BH-2:BD-1(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.

[0424] <Evaluation of Organic EL Components> • Color For the fabricated organic EL element, a spectroradiometer CS-2000 (manufactured by Conicaminodesk Ltd.) was used to measure the current density at 10.00 mA / cm². 2 The CIE1931 chromaticity coordinates (x, y) when voltage is applied to the component are shown in Table 1.

[0425] • External quantum efficiency (EQE) With a current density reaching 10 mA / cm 2 A voltage was applied to the organic EL element, and the EL emission spectrum was measured using a CS-2000 spectroradiometer (manufactured by Conicaminodes Co., Ltd.).

[0426] • Component lifespan At room temperature, with a current density of 50 mA / cm 2 A voltage is applied to the organic EL element in a certain way, and the time it takes for the brightness to reach 95% of the initial brightness is measured (LT95 (unit: h)).

[0427] Examples 2-6 In the formation of the first luminescent layer, the compounds shown in Table 1 were used instead of BH1-1 as the first host material. Otherwise, the organic EL element was fabricated and evaluated using the same method as in Example 1. The results are shown in Table 1.

[0428] Comparative Examples 1-4 In the formation of the first luminescent layer, the compounds shown in Table 1 were used instead of BH1-1 as the first host material. Otherwise, the organic EL element was fabricated and evaluated using the same method as in Example 1. The results are shown in Table 1.

[0429] Comparative Example 5 In the formation of the light-emitting layer, instead of the first and second light-emitting layers, BH-2 (the host material) and compound BD-1 (the dopant material) were co-deposited on the second hole transport layer at a ratio of 2% by mass to form a single light-emitting layer with a film thickness of 25 nm. Otherwise, an organic EL device was fabricated and evaluated using the same method as in Example 1. The results are shown in Table 1.

[0430] The component structure of the organic EL element in Comparative Example 5 is briefly shown below.

[0431] ITO(130) / HA(5) / HT-1(80) / HT-2(10) / BH-2:BD-1(25:2%) / 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.

[0432] [Table 1] .

[0433] In Table 1, the numbers in parentheses in the items representing the composition of the luminescent layer indicate the film thickness (unit: nm). Additionally, the percentage figures in parentheses indicate the proportion (mass%) of the latter compound in that layer.

[0434] As shown in Table 1, the elements of Examples 1-6 using the compound of one aspect of this application have the same degree of color and equivalent or higher efficiency than the elements of Comparative Examples 1-4, and achieve a longer lifetime.

[0435] It is also known that the elements of Examples 1 to 6 using the compound of one aspect of this application maintained the same level of chromaticity as the element of Comparative Example 5 having a single light-emitting layer, and exhibited high efficiency and showed equivalent or higher lifetime.

[0436] Example 7 <Fabrication of Organic EL Components> Organic EL elements are fabricated as described below.

[0437] 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 isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. This resulted in an ITO film thickness of 130nm.

[0438] 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, compounds HT-3 and HI-1 are co-evaporated in a manner that covers the transparent electrodes, with the proportion of compound HI-1 reaching 3% by mass, to form a hole injection layer with a film thickness of 10 nm.

[0439] Compound HT-3 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 85 nm.

[0440] Compound HT-4 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[0441] On the second hole transport layer, BH1-3 (the first host material) and compound BD-2 (the first dopant material) are co-deposited at a ratio of 2% by mass to form a first light-emitting layer with a film thickness of 5 nm.

[0442] On the first luminescent layer, compound BH-3 (the second host material) and compound BD-2 (the second dopant material) are co-deposited at a ratio of 2% by mass to form a second luminescent layer with a film thickness of 14 nm.

[0443] Compound ET-3 was deposited on the second luminescent layer to form the first electron transport layer with a thickness of 5 nm.

[0444] On the first electron transport layer, compounds ET-4 and Liq were co-deposited in a manner that achieved a Liq ratio of 50% by mass to form a second electron transport layer with a film thickness of 31 nm.

[0445] Liq was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0446] Metallic Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0447] The component structure of the organic EL element in Example 7 is briefly shown below.

[0448] ITO(130) / HT-3:HI-1(10:3%) / HT-3(85) / HT-4(5) / BH1-3:BD-2(5:2%) / BH-3:BD-2(14:2%) / ET-3(5) / ET-4:Liq(31:50%) / Liq(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.

[0449] <Evaluation of Organic EL Components> • Chromaticity, External Quantum Efficiency (EQE) For the fabricated organic EL elements, chromaticity and external quantum efficiency (EQE) were evaluated using the same method as in Example 1. The results are shown in Table 2.

[0450] • Component lifespan At room temperature, with a current density of 30 mA / cm 2 A voltage was applied to the organic EL element, and the time (LT95, h) until the brightness reached 95% of the initial brightness was measured. The results are shown in Table 2.

[0451] Examples 8-12 In the formation of the first luminescent layer, the compounds shown in Table 2 were used as the first host material instead of BH1-3. Otherwise, the organic EL element was fabricated and evaluated using the same method as in Example 7. The results are shown in Table 2.

[0452] Comparative Examples 6-8 In the formation of the first luminescent layer, the compounds shown in Table 2 were used as the first host material instead of BH1-3. Otherwise, the organic EL element was fabricated and evaluated using the same method as in Example 7. The results are shown in Table 2.

[0453] [Table 2] .

[0454] As shown in Table 2, the elements of Examples 7-12 using the compound of one aspect of this application have the same degree of chromaticity as the element of Comparative Example 6, and exhibit high efficiency and achieve a longer lifespan.

[0455] It is also known that the elements of Examples 7-12, which use compounds of one aspect of this application, exhibit superior color, high efficiency, and longer lifespan compared to the elements of Comparative Examples 7 and 8.

[0456] <Compound Synthesis> (Synthetic Example 1) Synthesis of BH1-1 BH1-1 was synthesized via the following synthetic route.

[0457] [Chemistry 182] Intermediate M-1 (1.75 g), intermediate M-2 (2.75 g), PdCl2(Amphos)3 (0.16 g), and sodium carbonate (0.97 g) were added to a reaction vessel. After purging the reaction vessel with argon, 1,2-dimethoxyethane (DME, 15 mL) and water (7 mL) were added, and the mixture was heated and stirred at 75 °C for 18 hours. After heating and stirring, the reaction solution was cooled, and the crude product obtained by distillation to remove the solvent was purified by column chromatography using silica gel and activated alumina, yielding compound BH1-1 as a white solid (0.78 g, yield 33%). Mass spectrometry analysis of this white solid revealed a molecular weight of 520.63 and an m / e ratio of 521, identifying it as compound BH1-1, the target compound.

[0458] (Synthetic Example 2) Synthesis of BH1-2 BH1-2 was synthesized via the following synthetic route.

[0459] [Chemistry 183] Intermediate M-3 was used in place of intermediate M-2, and compound BH1-2 was obtained as a white solid (0.45 g, yield 19%) by the same method as in Synthesis Example 1. Mass spectrometry analysis of the white solid revealed that it was identified as compound BH1-2, the target compound, with a molecular weight of 520.63 and m / e = 521.

[0460] (Synthetic Example 3) Synthesis of BH1-3 BH1-3 was synthesized via the following synthetic route.

[0461] [Chemistry 184] Intermediate M-3 (5.00 g), intermediate M-4 (5.80 g), tris(dibenzylacetone)dipalladium (0) (0.23 g), 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (DavePhos, 0.40 g), and cesium carbonate (12.3 g) were added to a reaction vessel. After purging the reaction vessel with argon, 1,4-dioxane (108 mL) and water (18 mL) were added, and the mixture was heated and stirred at 100 °C for 6 hours. After heating and stirring, the reaction solution was cooled, and the crude product obtained by distillation to remove the solvent was purified by column chromatography using silica gel and activated alumina, yielding compound BH1-3 as a white solid (5.03 g, yield 66%). Mass spectrometry analysis of this white solid showed a molecular weight of 611.82 and m / e = 612, identifying it as compound BH1-3, the target compound.

[0462] (Synthetic Examples 4-12) Synthesis of BH1-4 to BH1-12 The intermediates in the synthesis example of compound BH1-3 were modified as shown in Tables 3-4, and the synthesis was carried out using the same method as in synthesis example 3.

[0463] [Table 3] .

[0464] [Table 4] .

Claims

1. The compound shown in formula (1), [Chemistry 185] In equation (1), R1~R 10 each independently a hydrogen atom or a substituent Q; From R1 to R 10 Two or more adjacent groups are not bonded to each other; n1 is an integer from 0 to 3; When n1 is 0, (L1) n1 It is a single bond; When n1 is 2 or 3, multiple L1s can be the same or different from each other; L1 is a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group; Ar1 is an unsubstituted phenyl, an unsubstituted biphenyl, an unsubstituted naphthyl, or a substituted or unsubstituted fluorenyl, wherein the fluorenyl has a substituent that is an alkyl group having 1 to 18 carbon atoms; Ar2 is a group represented by the following formula (1A), (1B) or (1C); [Chemistry 186] In formulas (1A), (1B) and (1C), * denotes a bond with the benzene anthracene skeleton of formula (1); By R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 A group consisting of two or more adjacent elements Mutual bonding forms substituted or unsubstituted monocyclic rings. Mutual bonding forms substituted or unsubstituted fused rings, or They do not bond with each other; R does not form the single ring and the fused ring A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Each can be independently a hydrogen atom or a substituent Q; The substituent Q is: 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 Halogen atom, cyano 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.

2. The compound according to claim 1, wherein, By R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Groups consisting of two or more adjacent elements are not bonded to each other.

3. The compound according to claim 1 or 2, wherein, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 Each is independently a hydrogen atom, an unsubstituted phenyl group, an unsubstituted biphenyl group, or an unsubstituted naphthyl group.

4. The compound according to claim 1 or 2, wherein, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 It is a hydrogen atom.

5. The compound according to claim 1 or 2, wherein, R A15 R A18 R B17 Or R C12 To replace the base Q.

6. The compound according to claim 5, wherein, The substituent Q is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

7. The compound according to claim 1, wherein it is a compound represented by formula (1-1), (1-2), or (1-3) below. [Chemistry 187] In equations (1-1) to (1-3), R1 to R 10 Ar1, R A11 ~R A19 R B11 ~R B19 and R C11 ~R C19 As defined in equation (1).

8. The compound according to claim 1 or 2, wherein, R1~R 10 It is a hydrogen atom.

9. The compound according to claim 1, wherein it is a compound represented by any one of the following formulas (1-11) to (1-31), [Chem.188] In equations (1-11) to (1-31), Ar1 and R A12 ~R A13 R A15 ~R A18 R B12 ~R B17 R C12 ~R C13 and R C16 ~R C19 As defined in equation (1).

10. An organic electroluminescent element, which has the following characteristics: cathode, anode, and One or more organic layers disposed between the cathode and the anode; At least one of the organic layers contains the compound of claim 1 or 2.

11. The organic electroluminescent element according to claim 10, 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 compound.

12. The organic electroluminescent element according to claim 11, wherein, The light-emitting layer comprises a first layer and a second layer from the anode side, wherein the first layer contains the compound.

13. An electronic device having the organic electroluminescent element of claim 10.

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