Compound, organic electroluminescence element, and electronic device

Abstract

The present application relates to a compound, an organic electroluminescence element, and an electronic device. A compound represented by any one of the following formulas (1) to (3). In formulas (1) to (3), Ar1 is a substituted or unsubstituted aryl group of 4 or more monocyclic rings fused together, or a substituted or unsubstituted monovalent heterocyclic group of 4 or more monocyclic rings fused together.

Description

Technical Field

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

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

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

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

[0005] Existing technical documents Patent documents Patent document 1: International Publication No. 2023 / 127843. Summary of the Invention

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

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

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

[0009] 1. The compound represented by any of the following formulas (1) to (3), [Chemistry 1] [In equation (1),] Ar1 is Aryl groups formed by the fusion of four or more monocyclic rings, either substituted or unsubstituted, or A monovalent heterocyclic group consisting of four or more monocyclic rings, fused together, with or without substitution; n1 is an integer from 0 to 3; When n1 is 0, (L1) n1 It is a single bond; When n1 is 2 or more, two or more L1s are connected in series; when n1 is 2 or more, two or more L1s can be the same or different. L1 is single bond, Substituted or unsubstituted arylene groups with 6 to 12 cyclic carbon atoms, or A divalent heterocyclic group, substituted or unsubstituted, with 5 to 50 cyclic atoms; When Ar1 is a substituted or unsubstituted pyrene group, R 15 and R 17 ~R 20 One of them represents (L1). n1 The key; When Ar1 is a group other than a substituted or unsubstituted pyrene group, R 15 ~R 20 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 11 ~R 20 Each is independently a hydrogen atom or a substituent R; In equation (2), Ar1, L1, and n1 are defined as in equation (1) above; When Ar1 is a substituted or unsubstituted pyrene group, R 25 ~R 27 and R 29 ~R 30 One of them represents (L1). n1 The key; When Ar1 is a group other than a substituted or unsubstituted pyrene group, R 25 ~R 30 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 21 ~R 30 Each is independently a hydrogen atom or a substituent R; In equation (3), Ar1, L1, and n1 are defined as in equation (1) above; R 35 ~R 40 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 31 ~R 40 Each is independently a hydrogen atom or a substituent R; Substituent R is Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

[0010] 2. Organic electroluminescent devices, which have a cathode, anode, and One or more organic layers disposed between the aforementioned cathode and the aforementioned anode At least one of the aforementioned organic layers contains the compound described in section 1 above.

[0011] 3. An electronic device having the organic electroluminescent element described in 2 above.

[0012] According to the present invention, higher performance organic EL elements can be provided.

[0013] Brief description of the attached diagram Figure 1 This is a diagram illustrating the schematic configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

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

[0015] In this specification, in the chemical structural formula, hydrogen atoms, i.e. protium atoms, deuterium atoms, or tritium atoms, are bonded at positions where the symbols "R" or "D" representing deuterium atoms are not explicitly indicated.

[0016] 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, bridged compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of cyclic carbon atoms. The term "number of cyclic carbon atoms" as used below is the same unless otherwise stated. For example, the number of cyclic carbon atoms in a benzene ring is 6, in a naphthalene ring it is 10, in a pyridine ring it is 5, and in a furan ring it is 4. Additionally, for example, the number of cyclic carbon atoms in 9,9-diphenylfluorene is 13, and in 9,9'-spirodifluorene is 25.

[0017] 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.

[0018] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds) whose atoms are bonded to form a cyclic structure (e.g., monocyclic, fused-ring, and ring aggregates). Atoms that do not constitute a ring (e.g., hydrogen atoms ending 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 forming the pyridine ring. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Additionally, for example, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring bonded with hydrogen atoms or substituents is 10.

[0019] In this specification, the phrase "ZZ group with XX to YY carbon atoms, whether substituted or unsubstituted" 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.

[0020] In this specification, the phrase "ZZ group with XX to YY atoms of substituted or unsubstituted atoms" refers to the number of atoms in the ZZ group when it is unsubstituted, excluding the number of atoms in the substituents 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.

[0021] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0022] In this specification, "unsubstituted" in the context of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0023] 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 with AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0024] Substituents described in this specification The substituents described in this specification will be explained below.

[0025] Unless otherwise stated in this specification, the number of cyclic carbon atoms of the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0026] 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.

[0027] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" as stated in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0028] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0029] 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.

[0030] Unless otherwise stated in this specification, the number of cyclic carbon atoms in the "unsubstituted cycloalkyl group" described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0031] Unless otherwise stated 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.

[0032] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" specified in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0033] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene" as stated in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0034] • "Substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl"). In this specification, when "aryl" is mentioned alone, it includes both "unsubstituted aryl" and "substituted aryl".

[0035] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by substituents. Examples of "substituted aryl" include, for example, the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by substituents, and examples of substituted aryl in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes groups in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atoms of the aryl group itself are further replaced by substituents, and groups in Specific Example Group G1B below in which hydrogen atoms of the substituents are further replaced by substituents.

[0036] - Unsubstituted aryl (specific example group G1A): Phenyl, p - Biphenylyl, m - Biphenylyl, o - Biphenylyl, 4 - p - Terphenyl - 4 - yl, 3 - p - Terphenyl - 3 - yl, 2 - p - Terphenyl - 2 - yl, 4 - m - Terphenyl - 4 - yl, 3 - m - Terphenyl - 3 - yl, 2 - m - Terphenyl - 2 - yl, 4 - o - Terphenyl - 4 - yl, 3 - o - Terphenyl - 3 - yl, 2 - o - Terphenyl - 2 - yl, 1 - Naphthyl, 2 - Naphthyl, Anthryl, Benzoanthryl, Phenanthryl, Benzo[a]phenanthryl, Phenalenyl, Pyrenyl, Chrysenyl, Benzo[b]chrysenyl, Triphenylenyl, Benzo[c]triphenylenyl, Tetracenyl, Pentacenyl, Fluorenyl, 9,9'-Spirobi[fluorene]yl, Benzo[a]fluorenyl, Dibenzo[a,c]fluorenyl, Fluorenyl, Benzo[b]fluoranthenyl, Perylenyl, and a monovalent aryl derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP - 1) to (TEMP - 15).

[0037] [Chemical formula 2] [Chemical formula 3] - Substituted aryl (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 Phenylacetyl, 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.

[0038] • "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.

[0039] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0040] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0041] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, an unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and a substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group"). In this specification, when "heterocyclic group" is mentioned alone, it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0042] "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 Example Group G2A below where hydrogen atoms of the "unsubstituted heterocyclic group" are replaced, and examples of substituted heterocyclic groups in Example Group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include groups in Example Group G2B where hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself are further replaced by substituents, and groups in Example Group G2B where hydrogen atoms of the substituents are further replaced by substituents.

[0043] 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).

[0044] Specific example group G2B includes, for example: the following substituted heterocyclic groups containing nitrogen atoms (specific example group G2B1), substituted heterocyclic groups containing oxygen atoms (specific example group G2B2), substituted heterocyclic groups containing sulfur atoms (specific example group G2B3), and groups obtained 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).

[0045] • 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.

[0046] • 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.

[0047] • 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.

[0048] • A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4): [Chemistry 4] [Chemistry 5] 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.

[0049] 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 above general formulas (TEMP-16) to (TEMP-33) contains a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0050] • 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.

[0051] • 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].

[0052] • 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].

[0053] • A group obtained 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 selected from those bonded to the cyclic carbon atom of the monovalent heterocyclic group, X A and Y A When at least one of them is NH, the hydrogen atom bonded to the nitrogen atom, and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.

[0054] • "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".

[0055] "Substituted alkyl" refers to a group obtained by replacing one or more hydrogen atoms in an "unsubstituted alkyl" group with a substituent. Specific examples of "substituted alkyl" include groups obtained by replacing one or more hydrogen atoms in an "unsubstituted alkyl" group (specific example group G3A) with a substituent, and examples of substituted alkyl groups (specific example group G3B). In this specification, "alkyl" in "unsubstituted alkyl" refers to 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 obtained by further replacing hydrogen atoms of the alkyl group itself in the "substituted alkyl" group of specific example group G3B with a substituent, and groups obtained by further replacing hydrogen atoms of the substituents in the "substituted alkyl" group of specific example group G3B with a substituent.

[0056] • Unsubstituted alkyl groups (specific example group G3A): methyl, Ethyl, n-propyl, Isopropyl, n-Butyl, Isobutyl, sec-butyl, and tert-butyl.

[0057] • Substituted alkyl groups (specific example group G3B): Heptafluoropropyl (including isomers) Pentafluoroethyl, 2,2,2-Trifluoroethyl, and Trifluoromethyl

[0058] • "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), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group"). In this specification, when "alkenyl group" is mentioned alone, it includes both "unsubstituted alkenyl group" and "substituted alkenyl group".

[0059] "Substituted alkenyl" refers to a group obtained by replacing one or more hydrogen atoms in an "unsubstituted alkenyl" group with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) with a substituent 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 obtained by further replacing hydrogen atoms of the alkenyl group itself in the "substituted alkenyl" group of specific example group G4B with a substituent, and groups obtained by further replacing hydrogen atoms of the substituents in the "substituted alkenyl" group of specific example group G4B with a substituent.

[0060] • Unsubstituted alkenyl groups (specific example group G4A): vinyl, Allyl 1-Butenyl, 2-Butenyl, and 3-Butenyl.

[0061] • Substituted alkenyl groups (specific example group G4B): 1,3-Butadienyl, 1-Methylvinyl 1-Methylallyl, 1,1-Dimethylallyl, 2-Methylallyl, and 1,2-Dimethylallyl.

[0062] • "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".

[0063] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0064] • Unsubstituted alkynyl group (specific example group G5A): Acetylene • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl" as described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl"). In this specification, when "cycloalkyl" is mentioned alone, it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0065] "Substituted cycloalkyl" means a group obtained by replacing one or more hydrogen atoms in an "unsubstituted cycloalkyl" group with a substituent. Specific examples of "substituted cycloalkyl" include groups obtained by replacing one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). 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 obtained by replacing one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B with a substituent, and groups obtained by further replacing the hydrogen atoms of the substituents in the "substituted cycloalkyl" group of specific example group G6B with a substituent.

[0066] • Unsubstituted cycloalkyl groups (specific example group G6A): Cyclopropyl Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Adamantyl, 2-Adamantyl, 1-Norbornel alkyl, and 2-Norbornel alkyl.

[0067] • Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl.

[0068] • "-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).

[0069] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0070] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0071] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0072] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0073] In -Si(G1)(G1)(G1), the multiple G1s may be the same or different.

[0074] In -Si(G1)(G2)(G2), the multiple G2s may be the same or different.

[0075] In -Si(G1)(G1)(G2), multiple G1s may be the same or different.

[0076] In -Si(G2)(G2)(G2), the multiple G2s may be the same or different.

[0077] In -Si(G3)(G3)(G3), the multiple G3s may be the same or different.

[0078] In -Si(G6)(G6)(G6), the multiple G6s may be the same or different.

[0079] • "-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).

[0080] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0081] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0082] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0083] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0084] • "-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).

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

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

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

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

[0089] • "-N (R 906 (R) 907 The group shown in the figure” As described in this specification, -N(R) 906 (R) 907 Specific examples of the groups shown (specific example group G10) can be given as follows: -N(G1)(G1) -N(G2)(G2), -N(G1)(G2) -N(G3)(G3), and -N(G6)(G6).

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

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

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

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

[0094] In -N(G1)(G1), multiple G1s may be the same or different.

[0095] In -N(G2)(G2), multiple G2s may be the same or different.

[0096] In -N(G3)(G3), multiple G3s may be the same or different.

[0097] The multiple G6 values ​​in -N(G6) (G6) may be the same or different. • "Halogen atom" Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0098] • "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group obtained by replacing at least one hydrogen atom bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" with a fluorine atom, and also includes a group obtained by replacing all hydrogen atoms bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" with a fluorine atom (perfluoroalkyl). The number of carbon atoms in the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. "Substituted fluoroalkyl" refers to a group obtained by replacing one or more hydrogen atoms of the "fluoroalkyl" with a substituent. It should be noted that "substituted fluoroalkyl" as used in this specification also includes groups obtained by further replacing one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl" with a substituent, and groups obtained by further replacing one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl". 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.

[0099] • "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group obtained by replacing at least one hydrogen atom bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" with a halogen atom, and also includes a group obtained by replacing all hydrogen atoms bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" with a halogen atom. The number of carbon atoms in the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. "Substituted haloalkyl" refers to a group obtained by replacing one or more hydrogen atoms of the "haloalkyl" with a substituent. It should be noted that the term "substituted haloalkyl" as used in this specification also includes groups obtained by further replacing one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl" with a substituent, and groups obtained by further replacing one or more hydrogen atoms of the substituent in the "substituted haloalkyl". 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.

[0100] • "Substituted or unsubstituted alkoxy groups" As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.

[0101] • "Substituted or unsubstituted alkylthio groups" As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.

[0102] • "Substituted or unsubstituted aryloxy group" As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of cyclic carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0103] • "Substituted or unsubstituted arylthio groups" As a specific example of "substituted or unsubstituted aryl thiogroup" as described in this specification, it is the group indicated by -S (G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of cyclic carbon atoms of the "unsubstituted aryl thiogroup" is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.

[0104] • "Substituted or unsubstituted trialkylsilyl groups" As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0105] • "Substituted or unsubstituted aralkyl groups" As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group obtained by replacing the hydrogen atom of "alkyl" with "aryl" as a substituent, and is one form of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" in which "unsubstituted aryl" is substituted, and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50 unless otherwise specified in this specification, preferably 7 to 30, and more preferably 7 to 18.

[0106] 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.

[0107] The substituted or unsubstituted aryl groups described in this specification are preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, meta-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyrene, phenyl, triphenylene, fluorene, 9,9'-spirodifluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc., unless otherwise specified in this specification.

[0108] 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.

[0109] In this specification, the carbazoyl group, unless otherwise specified herein, refers to any of the following groups.

[0110] [Chemistry 6] In this specification, (9-phenyl)carbazolyl refers to any of the following groups unless otherwise specified in this specification.

[0111] [Chemistry 7] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding site.

[0112] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any of the following groups unless otherwise specified in this specification. [Chemistry 8] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * indicates the bonding site.

[0113] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl, etc.

[0114] • "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 aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in specific example group G1.

[0115] • "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise stated, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom from the heterocycle of the aforementioned "substituted or unsubstituted heterocyclic group". Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived by removing one hydrogen atom from the heterocycle of the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

[0116] • "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.

[0117] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably any group of the following general formulas (TEMP-42) to (TEMP-68). [Chemistry 9] [Chemistry 10] In the aforementioned general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0118] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * indicates the bonding site.

[0119] [Chemistry 11] In the aforementioned general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0120] Formulas Q9 and Q 10 They can form rings by bonding with each other through single bonds.

[0121] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * indicates the bonding site.

[0122] [Chemistry 12] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0123] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * indicates the bonding site.

[0124] The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any group of the following general formula (TEMP-69) to (TEMP-102) unless otherwise described in this specification.

[0125] [Chemistry 13] [Chemistry 14] [Chemistry 15] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0126] [Chemistry 16] [Chemistry 17] [Chemistry 18] [Chemistry 19] In the aforementioned general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0127] The above is an explanation of the substituents described in this specification.

[0128] • "The case where bonds are formed to create a ring" In this specification, the phrase "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, 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 elements bonded together to form a substituted or unsubstituted monocyclic ring," "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring," and "one or more groups of two or more adjacent elements not bonded together."

[0129] The following description addresses the cases of "a substituted or unsubstituted monocyclic ring formed by the mutual bonding of one or more groups of two or more adjacent elements" and "a substituted or unsubstituted fused ring formed by the mutual bonding of one or more groups of two or more adjacent elements" (hereinafter, these cases are sometimes collectively referred to as "the 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.

[0130] [Chemistry 20] For example, R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements that constitutes one group is R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0131] The phrase "one or more groups" means that two or more of the aforementioned groups consisting of two or more adjacent groups can simultaneously form a loop. For example, R 921 With R 922 Mutual bonding forms a ring Q AAnd 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).

[0132] [Chemistry 21] The case of rings formed by "groups consisting of two or more adjacent elements" includes not only the case of bonds consisting of "two" adjacent elements as in the previous example, but also the case of bonds 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 with the 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 .

[0133] [Chemistry 22] The formed "monocyclic ring" or "fused ring," as a structure consisting only of rings, can be a saturated ring or an unsaturated ring. Even when a "monocyclic ring" or "fused ring" is formed from "one of the groups consisting of two adjacent rings," the "monocyclic ring" or "fused ring" can still form a saturated ring or an unsaturated ring. For example, the ring Q formed in the aforementioned general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the aforementioned general formula (TEMP-105) A and ring Q C It is a "fused ring". The ring Q of the aforementioned general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q 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 QA It is a fused ring.

[0134] "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.

[0135] 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.

[0136] 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.

[0137] 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.

[0138] "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 using R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the carbon atoms of the bonded anthracene skeleton form a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The resulting ring is a benzene ring.

[0139] 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.

[0140] 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.

[0141] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0142] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0143] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0144] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0145] When “one or more groups consisting of two or more adjacent atoms” “are bonded together to form a substituted or unsubstituted monocyclic ring” or “are bonded together to form a substituted or unsubstituted fused ring”, unless otherwise specified in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms are bonded together to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of a parent skeleton and one or more but no more than 15 atoms selected from carbon, nitrogen, oxygen and sulfur atoms.

[0146] When a "monocyclic" or "fused-ring" ring has a substituent, the substituent is, for example, "any substituent" as described later. Specific examples of substituents when a "monocyclic" or "fused-ring" ring has a substituent are the substituents described in the section "Substituents described in this specification" above.

[0147] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, "any substituent" as described later. Specific examples of the substituents when the above-mentioned "monocyclic ring" or "fused ring" has a substituent are the substituents described in the section "Substituents described in this specification" above.

[0148] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" ("the case of forming a ring by bonding").

[0149] • 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.

[0150] 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 903 They 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 907When there are more than two, more than two R 907 They are the same or different.

[0151] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is a group selected from the following groups: 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.

[0152] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is a group selected from the following groups: 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] In this specification, the numerical range represented by "AA~BB" means a range that includes the value AA, which is listed before "AA~BB", as the lower limit and the value BB, which is listed after "AA~BB", as the upper limit.

[0157] [New Compounds] One aspect of the present invention relates to a compound represented by any one of the following formulas (1) to (3), [Chemistry 23] [In equation (1),] Ar1 is Aryl groups formed by the fusion of four or more monocyclic rings, either substituted or unsubstituted, or A monovalent heterocyclic group consisting of four or more monocyclic rings, fused together, with or without substitution; n1 is an integer from 0 to 3; When n1 is 0, (L1) n1 It is a single bond; When n1 is 2 or more, two or more L1s are connected in series; when n1 is 2 or more, two or more L1s can be the same or different. L1 is single bond, Substituted or unsubstituted arylene groups with 6 to 12 cyclic carbon atoms, or A divalent heterocyclic group, substituted or unsubstituted, with 5 to 50 cyclic atoms; When Ar1 is a substituted or unsubstituted pyrene group, R 15 and R 17 ~R 20 One of them represents (L1). n1 The key; When Ar1 is a group other than a substituted or unsubstituted pyrene group, R 15 ~R 20 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 11 ~R 20 Each is independently a hydrogen atom or a substituent R; In equation (2), Ar1, L1, and n1 are defined as in equation (1) above; When Ar1 is a substituted or unsubstituted pyrene group, R 25 ~R 27 and R 29 ~R 30 One of them represents (L1). n1 The key; When Ar1 is a group other than a substituted or unsubstituted pyrene group, R 25 ~R 30 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 21 ~R 30 Each is independently a hydrogen atom or a substituent R; In equation (3), Ar1, L1, and n1 are defined as in equation (1) above; R 35 ~R 40 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 31 ~R 40 Each is independently a hydrogen atom or a substituent R; Substituent R is Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

[0158] One aspect of the present invention relates to compounds that, when used in the organic layer of an organic EL device, can improve the device performance. For example, organic EL devices with low drive voltage and long lifetime can be realized. Furthermore, as another example, organic EL devices with low drive voltage, high external quantum efficiency, and long lifetime can be realized.

[0159] In this specification, "monocyclic fusion" means that two or more atoms constituting one monocyclic ring simultaneously become atoms constituting another monocyclic ring. In other words, it means that two monocyclic rings have two or more atoms as ring-forming atoms.

[0160] Therefore, a spirocycle with only one atom in common as a cyclic atom among two monocyclic rings does not fall under the category of "monocyclic fusion" in this specification.

[0161] There are no particular restrictions on the aryl monocyclic rings that constitute a fused ring structure consisting of four or more monocyclic rings, but they are usually 5- to 8-membered monocyclic rings, such as 5- or 6-membered monocyclic rings. The multiple monocyclic rings constituting the fused ring structure can be the same or different.

[0162] The monocyclic ring that makes up the aryl group is a hydrocarbon structure containing only carbon and hydrogen atoms.

[0163] There are no particular restrictions as long as the number of monocyclic rings constituting the aryl group (the number of fused monocyclic rings) is 4 or more, for example, 4 or more and 6 or less.

[0164] In one embodiment, the number of monocyclic rings constituting the aryl group is 4 or 5.

[0165] Examples of aryl groups formed by the fusion of four monocyclic rings include benzo[a]anthrayl, benzo[a]phenanthryl, pyrene, phenyl, triphenylene, tetraphenyl, benzo[a]fluorene, fluoranyl, and monovalent groups formed by removing one hydrogen atom from the structures represented by formulas (TEMP-7) to (TEMP-15) shown in the definition.

[0166] Examples of aryl groups formed by the fusion of five monocyclic rings include benzo[a]yl, benzo[a]triphenylene, benzo[a]pentaphenyl, dibenzo[a]fluorenyl, benzo[a]fluoranyl, peryl, and monovalent groups formed by removing one hydrogen atom from the structures represented by formulas (TEMP-1) to (TEMP-6) shown in the definition.

[0167] There are no particular restrictions on the monocyclic rings that constitute a monovalent heterocyclic group formed by the fusion of four or more monocyclic rings; they are typically 5- to 8-membered rings, such as 5- or 6-membered rings. The multiple monocyclic rings constituting the fused ring structure can be identical or different.

[0168] At least one ring constituting the heterocyclic group contains a heteroatom as a cyclizing atom. Other rings constituting the heterocyclic group may or may not contain heteroatoms as cyclizing atoms. Examples of rings that do not contain heteroatoms as cyclizing atoms include hydrocarbon rings containing only carbon and hydrogen atoms.

[0169] There are no particular restrictions on whether the heteroatom, which is included as a cyclic atom in at least one of the rings constituting the heterocyclic group, is an atom other than carbon and hydrogen. Examples include boron, nitrogen, oxygen, phosphorus, sulfur, and selenium atoms.

[0170] There are no particular restrictions as long as the number of monocyclic rings constituting the heterocyclic group (the number of fused monocyclic rings) is 4 or more, for example, 4 or more and 6 or less.

[0171] In one embodiment, the number of monocyclic rings constituting the heterocyclic group is 4 or 5.

[0172] Examples of monovalent heterocyclic groups formed by the fusion of four rings include benzoxanthinyl, benzocarbazoyl, naphthobenzofuranyl, azanaphthobenzofuranyl, diazanaphthobenzofuranyl, naphthobenzothienyl group, and monovalent groups formed by removing one hydrogen atom from the structures represented by formulas (TEMP-22) to (TEMP-33) shown in the definition.

[0173] Examples of monovalent heterocyclic groups formed by the fusion of five rings include dinaphthofuranyl, dinaphthothienyl group, azanaphthobenzothienyl group, diazanaphthobenzothienyl group, and monovalent groups formed by removing one hydrogen atom from the structures represented by formulas (TEMP-16) to (TEMP-21) shown in the definition.

[0174] In this specification, "Ar1 is a substituted or unsubstituted pyrene group" means that Ar1 is an unsubstituted or substituted pyrene group, and that no ring is formed between any adjacent substituents of the pyrene group.

[0175] Therefore, for example, if Ar1 is a substituted pyrene group, and two adjacent substituents on the pyrene group bond to each other to form an additional benzene ring, thereby making Ar1 a benzopyrene group, this falls under the category of "when Ar1 is a group other than a substituted or unsubstituted pyrene group".

[0176] In one embodiment, Ar1 is a group represented by any of the following formulas (Ar-1) to (Ar-3). [Chemistry 24] [In equation (Ar-1),] By R a11 ~R a20 One or more groups of two or more adjacent elements are bonded together to form a substituted or unsubstituted monocyclic or fused ring. R that does not form the aforementioned monocyclic or fused ring a11 ~R a20 One of them represents (L1). n1 The bond, or one of the aforementioned cyclic atoms in a monocyclic or fused ring, is bonded to (L1) by a single bond. n1 Bonding; R that does not form the aforementioned monocyclic or fused ring and does not represent the aforementioned single bond a11 ~R a20 Each is independently a hydrogen atom or a substituent R; In equation (Ar-2), X a21 For O, S, N (R) a29 ) or C(R) a30 )2; By R a21 ~R a28 One or more groups of two or more adjacent elements are bonded together to form a substituted or unsubstituted monocyclic or fused ring. R that does not form the aforementioned monocyclic or fused ring a21 ~R a29 One of them represents (L1). n1 The bond, or by R a21 ~R a28 One of the cyclic atoms in a monocyclic or fused ring formed by two or more adjacent atoms in a group is bonded to (L1) by a single bond. n1 Bonding; 2 Rs a30 They may bond together to form substituted or unsubstituted monocyclic or fused rings, or they may not form the aforementioned monocyclic or fused rings; R that does not form the aforementioned monocyclic or fused ring and does not represent the aforementioned single bond a21 ~R a30 Each is independently a hydrogen atom or a substituent R; 2 Rs a30 They can be the same or different; In equation (Ar-3), X a31 For O or S; By R a31 ~R a40 One or more groups of two or more adjacent elements are bonded together to form a substituted or unsubstituted monocyclic or fused ring. R that does not form the aforementioned monocyclic or fused ring a31 ~R a38 One of them represents (L1). n1 The bond, or one of the aforementioned cyclic atoms in a monocyclic or fused ring, is bonded to (L1) by a single bond. n1 Bonding; R that does not form the aforementioned monocyclic or fused ring and does not represent the aforementioned single bond a31 ~R a40 Each is independently a hydrogen atom or a substituent R; The substituent R is defined as in equations (1) to (3) above.

[0177] In one implementation, R a11 ~R a20 One or more groups of two or more adjacent rings are bonded together to form a substituted or unsubstituted monocyclic ring.

[0178] In one implementation, R a11 ~R a20 A benzene ring is formed by the bonding of two or more adjacent groups together, either substituted or unsubstituted.

[0179] In one implementation, R is selected a12 With R a13 group, R a13 With R a14 group, R a15 With R a16 group, R a20 With R a11 One group of the groups bonds with each other to form a substituted or unsubstituted benzene ring.

[0180] In one implementation, R is selected a21 With R a22 group, R a22 With R a23 group, R a23 With R a24 One group of the groups bonds with each other to form a substituted or unsubstituted benzene ring.

[0181] In one implementation, R a38 With R a39 With R a40 The groups bond together to form substituted or unsubstituted benzene rings.

[0182] In one implementation, X a21 For O or C (R) a30 2.

[0183] In one implementation, X a31 It is O.

[0184] In one implementation, Ar1 is Substituted or unsubstituted benzo[anthracene] Substituted or unsubstituted pyrene group Substituted or unsubstituted triphenylene Substituted or unsubstituted bases Substituted or unsubstituted benzofluorene, Substituted or unsubstituted naphthobenzofuranyl, or Substituted or unsubstituted benzoxanthine group.

[0185] In one implementation, Ar1 is Substituted or unsubstituted benzo[anthracene] Substituted or unsubstituted pyrene group, or Substituted or unsubstituted benzoxanthine group.

[0186] Ar1 can contain hydrogen atoms that are all protium atoms, or a mixture of protium and deuterium atoms, or all deuterium atoms.

[0187] In one embodiment, Ar1 has at least one deuterium atom.

[0188] In one embodiment, R in formulas (Ar-1) to (Ar-3) does not form a monocyclic or fused ring and does not represent a single bond. a21 ~R a40 It is a protium atom.

[0189] In one embodiment, R in formulas (Ar-1) to (Ar-3) does not form a monocyclic or fused ring and does not represent a single bond. a21 ~R a40 At least one of them is a deuterium atom.

[0190] In one embodiment, R in formulas (Ar-1) to (Ar-3) does not form a monocyclic or fused ring and does not represent a single bond. a21 ~R a40 It is a deuterium atom.

[0191] In this specification, a compound or group "having deuterium atoms" means that, in at least one of the hydrogen atoms 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.

[0192] In this specification, a specific hydrogen atom (or R as a hydrogen atom) x (X is an integer used to define the substituent) "Deuterium atom" means that in this hydrogen atom, the proportion of deuterium atoms is greater than that of naturally occurring atoms, relative to the total number of protium atoms and deuterium atoms.

[0193] Compared to the total number of protium and deuterium atoms, the proportion of deuterium atoms is greater than that found naturally, which can be confirmed by nuclear magnetic resonance (NMR) equipment.

[0194] In this specification, a specific hydrogen atom (or R as a hydrogen atom) x (X is a number or symbol used to define the substituent) "Protium atom" means that in this hydrogen atom, the proportion of deuterium atoms relative to the total number of protium atoms and deuterium atoms is less than the naturally occurring proportion.

[0195] The proportion of deuterium atoms relative to the total of protium and deuterium atoms can be confirmed by nuclear magnetic resonance (NMR) devices.

[0196] In one implementation, L1 is single key, or A substituted or unsubstituted cyclic aryl group with 6 to 12 carbon atoms.

[0197] In one implementation, L1 is single bond, Substituted or unsubstituted phenylene, or Substituted or unsubstituted naphthyl dimethyl.

[0198] In one embodiment, L1 has at least one deuterium atom.

[0199] In one implementation, L1 is a single bond.

[0200] In one implementation, n1 is 0, 1, or 2.

[0201] In one implementation, n1 is 0 or 1.

[0202] In one implementation, n1 is 0.

[0203] In one implementation, it is not represented by (L1). n1 The key of R 11 ~R 40 Each independently hydrogen atom, Alkyl groups with 1 to 10 carbon atoms, whether substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms substituted or unsubstituted aryl groups with 6 to 10 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 13 cyclic atoms, whether substituted or unsubstituted.

[0204] In one implementation, (L1) is not represented. n1 The key of R 11 ~R 40 Each independently hydrogen atom, Substituted or unsubstituted phenyl, or Substituted or unsubstituted naphthyl groups.

[0205] In one implementation, it is not represented by (L1). n1 The key of R 11 ~R 40 It is a hydrogen atom.

[0206] In one implementation, R is a hydrogen atom 11 ~R 40 It is a protium atom.

[0207] In one implementation, R is a hydrogen atom 11 ~R 40 It is a deuterium atom.

[0208] In one embodiment, the compound represented by any of the aforementioned formulas (1) to (3) is a compound represented by any of the following formulas (1-1) to (1-3), (2-1) to (2-3) and (3-1) to (3-3).

[0209] [Chemistry 25] [Chemistry 26] [Chemistry 27] In equations (1-1) to (1-3), (2-1) to (2-3), and (3-1) to (3-3), n1, L1, R 11 ~R 40 As defined in equations (1) to (3) above; R 101 ~R 112 R 201 ~R 210 and R 301 ~R 310 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 101 ~R 112 R 201 ~R 210 and R 301 ~R 310 Each is independently a hydrogen atom or a substituent R; The substituent R is defined as in equations (1) to (3) above.

[0210] It should be noted that, as is obvious from the definition, the compounds shown in formulas (1-2) belong to the case where "Ar1 is a substituted or unsubstituted pyrene group" in the compounds shown in formula (1). Therefore, R 15 and R 17 ~R 20 One of them represents (L1). n1 The key.

[0211] Similarly, the compound shown in formula (2-2) belongs to the case where "Ar1 is a substituted or unsubstituted pyrene group" in the compound shown in formula (2). Therefore, R 25 ~R 27 and R 29 ~R 30 One of them represents (L1). n1 The key.

[0212] In one implementation, it is not represented by (L1). n1 The key of R 101 ~R 112 R 201 ~R 210 and R 301 ~R 310 It is a hydrogen atom.

[0213] In one embodiment, the compound represented by any of the aforementioned formulas (1) to (3) is a compound represented by any of the following formulas (1-11), (2-11), (2-12), and (2-21). [Chemistry 28] [Chemistry 29] In equations (1-11), (2-11), (2-12), and (2-21), n1, L1, and R... 11 ~R 14 R 16 ~R 20 R 21 ~R 24 and R 26 ~R 30 As defined in equations (1) to (3) above; R 101 ~R 112 and R 202 ~R 210 Each is independently a hydrogen atom or a substituent R; The substituent R is defined as in equations (1) to (3) above.

[0214] In one embodiment, the substituent in the “substituted or unsubstituted” cases in formulas (1) to (3) 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.

[0215] R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted.

[0216] In one embodiment, the substituent in the “substituted or unsubstituted” cases of formulas (1) to (3) is a group selected from the following groups: 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.

[0217] In one embodiment, the substituent in the “substituted or unsubstituted” cases of formulas (1) to (3) is a group selected from the following groups: 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.

[0218] As one aspect of the present invention, the compounds described in the examples are examples of compounds that may be cited.

[0219] The compounds involved in one aspect of the present invention can be synthesized, according to embodiments, by using known alternative reactions or starting materials corresponding to the target.

[0220] The following describes specific examples of compounds involved in one aspect of the present invention, but these are merely illustrative and the compounds involved in one aspect of the present invention are not limited to the specific examples described below.

[0221] [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] .

[0222] [Materials for Organic Electroluminescent Devices] The compounds involved in one aspect of the present invention are useful as materials for organic EL elements, for example as materials used in the light-emitting layer of organic EL elements.

[0223] [Organic EL element] An organic EL element relating to one aspect of the present invention will be described.

[0224] An organic EL element according to one aspect of the present invention has: a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers contains a compound according to one aspect of the present invention (a compound represented by any of formulas (1) to (3)).

[0225] One aspect of the present invention relates to an organic EL element that, by having the above-described configuration, can improve performance.

[0226] In one embodiment, the light-emitting layer comprises, in sequence, an anode, a light-emitting layer, and a cathode, wherein at least one organic layer of the light-emitting layer comprises a compound according to one aspect of the present invention.

[0227] One aspect of the present invention relates to an organic EL element having the above-described configuration, which can improve performance and enable organic EL elements with, for example, low drive voltage and long lifetime. While the reasons for these effects may not be definitively established, it is believed that the use of the aforementioned compound improves hole injection in the layer, thereby exhibiting these effects.

[0228] In one embodiment, the light-emitting layer of the organic EL element according to one aspect of the present invention further comprises a compound represented by any of the following formulas (D11) to (D41). [Chemistry 100] For equations (D11) to (D41), as will be described later.

[0229] (The compound represented by formula (D11)) The compound represented by formula (D11) will be described.

[0230] [Chemistry 101] [In equation (D11),] Each of the three Zs is an independent CR a Or nitrogen atoms; Rings A1 and A2 are each independent of each other. Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 carbon atoms, or Heterocycles with 5 to 50 cyclic atoms, either substituted or unsubstituted; R a When there are multiple R, it is composed of multiple R a One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other; 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. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form 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. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form 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 Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted; R 901 ~R 907 As defined in equations (1) to (3) above.

[0231] The aromatic hydrocarbon rings of A1 and A2 have the same structure as compounds obtained by introducing hydrogen atoms into the aforementioned aryl groups with 6 to 50 carbon atoms.

[0232] The "aromatic hydrocarbon rings" of A1 and A2 contain two carbon atoms on the fused 2-ring structure at the center of the aforementioned formula (D11) as cyclic atoms.

[0233] As a specific example of "aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms", compounds obtained by introducing hydrogen atoms into "substituted or unsubstituted aryl groups" as described in Specific Example Group G1 can be cited.

[0234] The "heterocyclic" rings A1 and A2 have the same structure as compounds obtained by introducing hydrogen atoms into the aforementioned "heterocyclic groups with 5 to 50 cyclic atoms".

[0235] The "heterocyclic" rings A1 and A2 contain two carbon atoms on the fused 2-ring structure at the center of the aforementioned formula (D11) as cyclic atoms.

[0236] As a specific example of "a heterocycle with 5 to 50 cyclic atoms, whether substituted or unsubstituted", compounds obtained by introducing hydrogen atoms into the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2 can be cited.

[0237] 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 heterocyclic ring as an Al ring.

[0238] 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.

[0239] In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D11a).

[0240] In one embodiment, at least two of Ra, Rb, and Rc are groups represented by the following formula (D11a).

[0241] [Chemistry 102] [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, substituted or unsubstituted, with 5 to 30 cyclic atoms; Ar D101 for Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or The group represented by the following formula (D11b); [Chemistry 103] (In equation (D11b), L D102 and L D103 Each independently single bond, Substituted or unsubstituted arylene groups with 6 to 30 cyclic carbon atoms, or A divalent heterocyclic group, substituted or unsubstituted, with 5 to 30 cyclic atoms; By Ar D102 and Ar D103 The group They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other; Ar does not form the aforementioned monocyclic or fused rings D102 and Ar D103 Each independently substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0242] The following are specific examples of compounds represented by formula (D11), but these are merely illustrative and the compounds represented by formula (D11) are not limited to the specific examples described below. [Chemistry 104] .

[0243] (The compound represented by formula (D21)) The compound represented by formula (D21) will be described.

[0244] [Chemistry 105] [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 is bonded to each other to form a divalent group as shown in the following formula (D22); R D205 With R D206 R D206 With R D207 and R D207 With R D208 At least one group of them is bonded to each other to form a divalent group as shown in the following formula (D23); [Chemistry 106] (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); 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); X D2 For oxygen atoms, sulfur atoms, or NR D209 ; R that does not form the divalent groups shown in formulas (D22) and (D23) above, and is not the monovalent group shown in formula (D24) above. D201 ~R D208 R that is not a monovalent group as shown in the aforementioned formula (D24) D211 ~R D214 and R D221 ~R D224 and R D209 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted; [Chemistry 107] (In equation (D24), Ar D201 and Ar D202 Each independently substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted; L D201 ~L D203 Each independently single bond, substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms Substituted or unsubstituted divalent heterocyclic groups with 5 to 30 cyclic atoms, or A divalent linking group formed by bonding 2 to 4 groups selected from substituted or unsubstituted aryl groups with 6 to 30 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 equations (1) to (3) above.

[0245] 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.

[0246] As for the compounds represented by formula (D21), in addition to the compounds described in International Publication No. 2014 / 104144, the following compounds may be listed as specific examples, but these are merely examples and the compounds represented by formula (21) are not limited to the following specific examples.

[0247] [Chemistry 108] (The compound represented by formula (D31)) The compound represented by formula (D31) will be described.

[0248] [Chemistry 109] [In equation (D31),] By R D301 ~R D307 and R D311 ~R D317 Two or more adjacent rings form a group of one or more rings that are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other. R that does not form the aforementioned single ring and the aforementioned fused ring D301 ~R D307 and R D311 ~R D317 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R D321 and R D322 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 As defined in equations (1) to (3) above.

[0249] "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 consisting of R D302 and R D303 The group consisting of R D303 and R D304 The group consisting of R D305 and R D306 The group consisting of R D306 and R D307 The group consisting of R D301 R D302 and R D303 Combinations of groups, etc.

[0250] In one implementation, R D301 ~R D307 and R D311 ~R D317 At least one of them is -N(R) 906 (R) 907 ).

[0251] In one implementation, R D301 ~R D307 and R D311 ~R D317 Two of them are -N (R) 906 (R) 907 ).

[0252] In one implementation, R D301 ~R D307 and R D311 ~R D317 Each independently hydrogen atom, substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0253] The following describes specific examples of compounds represented by formula (D31), but these are merely illustrative examples, and the compounds represented by formula (D31) are not limited to the specific examples described below.

[0254] [Chemical 110] [Chemistry 111] (The compound represented by formula (D41)) The compound represented by formula (D41) will be described.

[0255] [Chemistry 112] [In equation (D41),] Rings a, b, and c are each independently... Aromatic hydrocarbon rings with 6 to 50 carbon atoms, substituted or unsubstituted, Heterocycles with 5 to 50 cyclic atoms, either substituted or unsubstituted; R D401 and R D402 Each ring independently bonds to the aforementioned ring a, ring b, or ring c to form a substituted or unsubstituted heterocycle, or they do not bond at all; R that does not form the aforementioned heterocycle D401 and R D402 Each independently Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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].

[0256] Rings a, b, and c are rings fused with a fused 2-ring structure in the center of formula (D41), which consists of a B atom and two N atoms (an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a heterocycle with 5 to 50 substituted or unsubstituted cyclic carbon atoms).

[0257] 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 2-ring structure at the center of formula (D41) as cyclic atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms in the fused 2-ring structure at the center of formula (D41) as cyclic atoms. Specific examples of "aromatic hydrocarbon rings with 6 to 50 substituted or unsubstituted cyclic carbon atoms" include compounds formed by introducing hydrogen atoms into the "aryl" group described in specific example group G1.

[0258] 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 of the fused 2-ring structure at the center of formula (D41) as cyclic atoms. The "heterocycles" of rings b and c include the two carbon atoms of the fused 2-ring structure at the center of formula (D41) as cyclic atoms. Specific examples of "heterocycles with 5 to 50 substituted or unsubstituted cyclic atoms" include compounds formed by introducing hydrogen atoms into the "heterocyclic group" described in specific example group G2.

[0259] R D401 and R D402 Each ring can independently bond with ring a, ring b, or ring c to form substituted or unsubstituted heterocycles. In this case, the heterocycle contains the nitrogen atom on the fused 2-ring structure at the center of formula (D41). The heterocycle in this case can contain heteroatoms other than the nitrogen atom. Specifically, R D401 and R D402 Bonding to ring a, b, or c refers to the bonding between atoms that make up ring a, b, or c and atoms that make up ring R. D401 and R D402 Atomic bonding. For example, R D401 It can bond with an α ring to form a ring containing R D401 A nitrogen-containing heterocycle in which two rings (or three or more rings) are fused to an a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing heterocyclic groups with two or more rings fused to each other in Specific Example Group G2.

[0260] R D401 Cases involving b-ring bonding, R D402 Cases involving α-ring bonding and R D402 The situation regarding bonding with the c-ring is the same as described above.

[0261] In one embodiment, rings a, b, and c in formula (D41) are each independently an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted cyclic carbon atoms.

[0262] In one embodiment, rings a, b, and c in formula (D41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0263] In one implementation, R in equation (D41) D401 and R D402 Each is independently an aryl group with 6 to 50 cyclic carbon atoms (substituted or unsubstituted) or a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms (substituted or unsubstituted), preferably an aryl group with 6 to 50 cyclic carbon atoms (substituted or unsubstituted).

[0264] In one embodiment, the compound represented by formula (D41) is the compound represented by formula (D42) below. [Chemistry 113] (In equation (D42), R D401A With selection from R D411 and R D421 One or more of them are bonded to form a substituted or unsubstituted heterocycle, or they are not bonded; R D402A With selection from R D413 and R D414 One or more of them are bonded to form a substituted or unsubstituted heterocycle, or they are not bonded; R does not form the aforementioned substituted or unsubstituted heterocycles D401A and R D402A Each independently Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R D411 ~R D421 Two or more adjacent rings in one or more groups are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other; R does not form the aforementioned substituted or unsubstituted heterocycles or the aforementioned substituted or unsubstituted saturated or unsaturated rings. D411 ~R D421Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 As defined in equations (1) to (3) above.

[0265] R in equation (D42) D401A and R D402A R is the same as in equation (D41) D401 and R D402 The corresponding functional group.

[0266] For example, R D401A With R D411 Bonding can form nitrogen-containing heterocycles with two-ring fusion (or three-ring fusion or more) formed by the fusion of the rings containing them with a benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing two-ring fused or more 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.

[0267] 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 D412Bonding can form structures such as 6-membered rings, fused benzene rings, indole rings, pyrrole rings, benzofuran rings, or benzothiophene rings, with the fused rings becoming naphthyl rings, carbazole rings, indole rings, dibenzofuran rings, or dibenzothiophene rings.

[0268] In one implementation, R does not contribute to ring formation. D411 ~R D421 Each of the following 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 atoms.

[0269] In one implementation, R does not contribute to ring 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.

[0270] In one implementation, R does not contribute to ring formation. D411 ~R D421 Alkyl groups, each consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms.

[0271] In one implementation, R does not contribute to ring formation. D411 ~R D421 Each of the following is an alkyl group consisting of 1 to 50 hydrogen atoms, either substituted or unsubstituted: R D411 ~R D421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0272] In one embodiment, the compound represented by formula (D42) is the compound represented by formula (D43). [Chemistry 114] (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 R D451 Bonding forms substituted or unsubstituted heterocycles, or no bonding occurs; R D441 With R D442 They may bond to form substituted or unsubstituted heterocycles, or they may not bond at all; R D431~R D451 Two or more adjacent rings in one or more groups are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other; 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 hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 As defined in equations (1) to (3) above.

[0273] R D431 Can be used with R D446 Bonding forms substituted or unsubstituted heterocycles. For example, R D431 With R D446 Bonding can form R D446 A nitrogen-containing heterocycle consisting of a bonded benzene ring, a ring containing nitrogen, and a benzene ring corresponding to an a ring, fused together to form a 3-ring fused or more nitrogen-containing heterocycle. Specific examples of such nitrogen-containing heterocycles include compounds corresponding to the nitrogen-containing 3-ring fused or more heterocyclic groups in specific example group G2. R D433 With R D447 Bonding situation, R D434 With R D451 The bonding situation and R D441 With R D442 The bonding situation is the same as described above.

[0274] In one implementation, R does not contribute to ring formation.D431 ~R D451 Each of the following 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 atoms.

[0275] In one implementation, R does not contribute to ring 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.

[0276] In one implementation, R does not contribute to ring formation. D431 ~R D451 Alkyl groups, each consisting of 1 to 50 hydrogen atoms, or substituted or unsubstituted carbon atoms.

[0277] In one implementation, R does not contribute to ring formation. D431 ~R D451 Each of the following is an alkyl group consisting of 1 to 50 hydrogen atoms, either substituted or unsubstituted: R D431 ~R D451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0278] In one embodiment, the compound represented by the aforementioned formula (D43) is a compound represented by the following formula (D43A). [Chemistry 115] (In formula (D43A), R D461 for hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted; R D462 ~R D465 Each independently Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or Aryl groups, with or without substituted cyclic carbon atoms, numbering 6 to 50.

[0279] In one implementation, R D461 ~R D465 Each is independently an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms.

[0280] In one implementation, R D461 ~R D465 Each is an alkyl group, either substituted or unsubstituted, having 1 to 50 carbon atoms.

[0281] In one embodiment, the compound represented by the aforementioned formula (D43) is the compound represented by the following formula (D43B). [Chemistry 116] (In formula (D43B), R D471 and R D472 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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, either substituted or unsubstituted; R D473 ~R D475 Each independently Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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, either substituted or unsubstituted; R 906 and R 907As defined in equations (1) to (3) above.

[0282] In one embodiment, the compound represented by the aforementioned formula (D43) is a compound represented by the following formula (D43B'). [Chemistry 117] (In equation (D43B'), R) D472 ~R D475 As defined in the aforementioned formula (D43B).

[0283] In one implementation, R D471 ~R D475 At least one of them is Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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, either substituted or unsubstituted.

[0284] In one implementation method R D472 for hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted -N(R 906 (R) 907 ),or Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted. R D471 and R D473 ~R D475 Each independently Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted -N(R 906 (R) 907 ),or Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted.

[0285] In one embodiment, the compound represented by the aforementioned formula (D43) is a compound represented by the following formula (D43C). [Chemistry 118] (In formula (D43C), R D481 and R D482 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or Aryl groups with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted; R D483 ~R D486 Each independently Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted. Substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, or Aryl groups, with or without substituted cyclic carbon atoms, numbering 6 to 50.

[0286] In one embodiment, the compound represented by the aforementioned formula (D43) is a compound represented by the following formula (D43C'). [Chemistry 119] (In equation (D43C'), R) D483 ~R D486 As defined in the aforementioned formula (D43C).

[0287] In one implementation, R D481 ~R D486 Each is independently an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms.

[0288] In one implementation, R D481 ~R D486 Each is an aryl group, either substituted or unsubstituted, with 6 to 50 cyclic carbon atoms.

[0289] In one embodiment, the compound represented by the aforementioned formula (D41) is the compound represented by the following formula (D44).

[0290] [Chemistry 120] (In equation (D44), X D401 For O or S; R D401B With selection from R D487 and R D497 One or more of them are bonded to form a substituted or unsubstituted heterocycle, or they are not bonded; R D402B With selection from R D489 and R D490 One or more of them are bonded to form a substituted or unsubstituted heterocycle, or they are not bonded; R does not form the aforementioned substituted or unsubstituted heterocycles D401B and R D402B Each independently Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R D487 ~R D497 Two or more adjacent rings in one or more groups are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or they are not bonded to each other; R does not form the aforementioned substituted or unsubstituted heterocycles or the aforementioned substituted or unsubstituted saturated or unsaturated rings. D487 ~R D497 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted; R 901 ~R 907 As defined in equations (1) to (3) above. In one implementation, R D401B and R D402B Each is independently an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms.

[0291] In one implementation, R D487 ~R D497 Each is independently an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms.

[0292] For the compound shown in formula (D41), first use a linking group (containing NR) D401 Groups and containing NR D402 The intermediate is produced by bonding rings a, b, and c together with a group containing B (reaction 1). The final product is produced by bonding rings a, b, and c together with a linking group (a group containing B). In reaction 1, amination reactions such as the Buchwald-Hartwig reaction can be used. In reaction 2, tandem hetero-Friedel-Crafts reactions can be used.

[0293] The following describes specific examples of compounds represented by formula (D41), but these are merely illustrative, and the compounds represented by formula (D41) are not limited to the specific examples described below. [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] In addition to the compounds shown in formulas (D11), (D21), (D31), or (D41) above, the aforementioned light-emitting layer may also use, for example, the compounds shown below. [Chemistry 134] In one embodiment, the aforementioned light-emitting layer contains a compound represented by formula (D41).

[0294] 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 (a compound represented by any of formulas (1) to (3)) according to one aspect of the present invention.

[0295] In one embodiment, the aforementioned light-emitting layer has a first layer and a second layer from the anode side, and further has one or more layers, wherein the aforementioned first layer contains a compound (a compound represented by any of formulas (1) to (3)) according to one aspect of the present invention.

[0296] In one embodiment, the first layer contains a compound according to one aspect of the present invention and a compound represented by any of the aforementioned formulas (D11) to (D41).

[0297] In one embodiment, the first layer comprises a compound involved in one aspect of the invention as the host material (sometimes also referred to as the matrix material).

[0298] In one embodiment, the first layer further comprises a dopant material.

[0299] In one embodiment, the first 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 luminescent material).

[0300] In one embodiment, the first layer contains dopant material in an amount exceeding 1.1% by mass, 1.2% by mass, or 1.5% by mass of the total mass of the first layer.

[0301] In one embodiment, the first layer contains dopant material in an amount of less than 10% by mass, less than 7% by mass, or less than 5% by mass of the total mass of the first layer.

[0302] In one embodiment, the first layer contains the main material in an amount of 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the total mass of the first layer.

[0303] In one embodiment, the first layer contains the host material in an amount of less than 99% by mass of the total mass of the first layer.

[0304] The first layer may also contain materials other than the host material and dopant materials.

[0305] The first layer can contain only one host material or two or more. The first layer can contain only one dopant material or two or more.

[0306] The luminescent layer is a layer containing a highly luminescent substance, and various materials can be used. For example, in addition to the compounds shown in any of the formulas (D11) to (D41) above, fluorescent compounds and phosphorescent compounds can also be used as highly luminescent substances. Fluorescent compounds are compounds that can emit light from a singlet excited state, and phosphorescent compounds are compounds that can emit light from a triplet excited state.

[0307] 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.

[0308] 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.

[0309] The luminescent layer can also be configured such that the highly luminescent substance (guest material) is dispersed in other substances (host material). As for the substance used to disperse the highly luminescent substance, various substances can be used besides the materials used in this invention as described above (the compounds involved in one aspect of this invention). Preferably, a substance with a higher lowest empty orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) compared to the highly luminescent substance is used.

[0310] 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.

[0311] Alternatively, delayed fluorescence (thermally activated delayed fluorescence) compounds can also be used as the host material. The luminescent layer preferably comprises the materials used in this invention as described above and the delayed fluorescence host compound.

[0312] In addition to the materials used in this invention as described above, the light-emitting layer may also contain or not contain the other substances mentioned above.

[0313] (Level 2) The second layer contains at least one compound that is different from the first layer described above. In one embodiment, the second layer contains a host material (the second host material). As the host material, substances listed as the host material (the first host material) of the first layer described above can be used.

[0314] In one embodiment, the second host material is a compound different from the first host material contained in the first layer.

[0315] Alternatively, delayed fluorescence (thermally activated delayed fluorescence) compounds can also be used as the host material. The luminescent layer may also contain the compounds described above in one aspect of the present invention, and the delayed fluorescence host compound.

[0316] In one embodiment, the second layer further comprises a dopant material (the second dopant material). As the dopant material, substances listed above as the dopant material of the first layer (the first dopant material) can be used.

[0317] In one embodiment, the second dopant material is a compound represented by any of the formulas (D11) to (D41) above.

[0318] In one embodiment, the second dopant material is a compound different from the first dopant material.

[0319] In one embodiment, the second dopant material is the same compound as the first dopant material.

[0320] In one embodiment, the second layer contains dopant material in an amount exceeding 1.1% by mass, 1.2% by mass, or 1.5% by mass of the total mass of the second layer.

[0321] In one embodiment, the second layer contains dopant material in an amount of less than 10% by mass, less than 7% by mass, or less than 5% by mass of the total mass of the second layer.

[0322] In one embodiment, the second layer contains the main material in an amount of 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the total mass of the second layer.

[0323] In one embodiment, the second layer contains the host material in an amount of less than 99% by mass of the total mass of the second layer.

[0324] The second layer may also contain materials other than the host material and dopant materials.

[0325] 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.

[0326] The second layer can be a fluorescent luminescent layer or a phosphorescent luminescent layer.

[0327] In one embodiment, the second layer is a fluorescent light-emitting layer.

[0328] In one embodiment, an organic EL element according to one aspect of the present invention has a hole transport region between the aforementioned anode and the aforementioned light-emitting layer.

[0329] In one embodiment, an organic EL element according to one aspect of the present invention has an electron transport region between the aforementioned cathode and the aforementioned light-emitting layer.

[0330] Reference Figure 1 The following describes the general configuration of an organic EL element according to one aspect of the present invention.

[0331] 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.

[0332] As a representative component configuration of the organic EL element of the present invention, an example can be shown that has the following structure stacked on a substrate.

[0333] (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, 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 these layers, or it can be composed of only a portion of these layers. Furthermore, for each of the above layers, two or more types of layers can be used; for example, two different types of hole transport layers can be stacked.

[0334] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0335] 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 these layers, or it can be composed of only a portion of these layers. Furthermore, for each of the above layers, two or more types of layers can be used; for example, two electron transport layers with different compositions can be stacked.

[0336] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0337] Hereinafter, components that can be used in an organic EL element according to one aspect of the present invention, and materials other than the compounds described above that constitute each layer, will be described.

[0338] (Substrate) The substrate is used 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 (flexible) substrate that can be bent; examples include plastic substrates containing polycarbonate or polyvinyl chloride.

[0339] (anode) The anode formed on the substrate preferably uses metals, alloys, conductive compounds, and mixtures thereof with a high work function (specifically 4.0 eV or higher). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride).

[0340] (hole injection layer) The hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability can also 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 polymers, polymers, etc.).

[0341] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used for the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used. In addition, any other substance can be used as long as it has high hole transport capacity compared to electrons. It should be noted that the layer containing the high hole transport capacity can be fabricated not only as a single layer, but also as an object obtained by stacking two or more layers containing the above-mentioned substances.

[0342] (Electron blocking layer, hole blocking layer, exciton blocking layer) Electron blocking layers, hole blocking layers, exciton (triple state) blocking layers, etc., can also be set adjacent to the light-emitting layer.

[0343] 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.

[0344] (Electron transport layer) The electron transport layer is a layer containing substances with high electron transport properties. Electron transport layers can use 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymeric compounds.

[0345] (Electron injection layer) The electron injection layer is a layer containing a material with high electron injection capability. Electron injection layers can utilize metal complexes such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium 8-hydroxyquinoline (Liq), as well as lithium oxides (LiO). x Alkali metals, alkaline earth metals, or their compounds, etc.

[0346] (cathode) The cathode is preferably made of metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs); alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and alloys containing them (e.g., MgAg, AlLi); and rare earth metals such as europium (Eu) and ytterbium (Yb) and alloys containing them.

[0347] In an organic EL element according to one aspect 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 lower level, and improve luminous efficiency, the thickness is usually in the range of several nm to 1 μm.

[0348] In the organic EL element according to one aspect of the present invention, the method of forming each layer is not particularly limited. Existing and 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 such as immersion in a solution dissolved in a solvent, spin coating, casting, rod coating, roll coating, etc.

[0349] [Electronic devices] An electronic device according to one aspect of the present invention is characterized in that it comprises an organic EL element according to one aspect of the present invention.

[0350] Specific examples of electronic devices include display components such as organic EL panel modules; display devices for televisions, mobile phones, or personal computers; and light-emitting devices such as lighting fixtures or vehicle lamps. Example

[0351] <Compound> The following shows the compounds of formulas (1) to (3) used in the manufacture of the organic EL elements in Examples 1 to 16.

[0352] [Chemistry 135] [Chemistry 136] The following are comparative example compounds used in the manufacture of the organic EL elements in Comparative Examples 1 to 6.

[0353] [Chemistry 137] The structures of other compounds used in the manufacture of the organic EL elements in Examples 1-16 and Comparative Examples 1-6 are shown below.

[0354] [Chemistry 138] [Chemistry 139]

[0355] Example 1 <Fabrication of Organic EL Components> Organic EL components are fabricated as follows.

[0356] A 25mm × 75mm × 1.1mm thick glass substrate (manufactured by Geomatics Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[0357] The cleaned glass substrate with transparent electrodes is mounted on the substrate support of the vacuum evaporation apparatus. First, compound HI-1 is evaporated to cover the transparent electrodes on the side where they are formed, and a hole injection layer with a thickness of 5 nm is formed into a film.

[0358] Compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[0359] Compound EB-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[0360] On the second hole transport layer, compound Inv-1 (host material) and compound BD-1 (dopant material) are co-deposited in a ratio of 2% by mass to form the first light-emitting layer with a thickness of 5 nm.

[0361] On the first luminescent layer, compound BH-2 (host material) and compound BD-1 (dopant material) are co-deposited in a ratio of 2% by mass to form a second luminescent layer with a thickness of 20 nm.

[0362] Compound HB-1 was deposited on the second luminescent layer to form the first electron transport layer with a thickness of 10 nm.

[0363] Compound ET-1 was deposited on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm.

[0364] LiF was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0365] Metallic Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0366] If we simply show the component configuration of the organic EL element of Example 1, it is as follows.

[0367] ITO(130) / HI-1(5) / HT-1(80) / EB-1(10) / Inv-1:BD-1(5:2%) / BH-2:BD-1(20:2%) / HB-1(10) / ET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Additionally, the percentages in parentheses indicate the proportion (by mass) of the latter compound in that layer.

[0368] <Evaluation of Organic EL Components> • Component lifespan At room temperature, with a current density of 50 mA / cm 2 A voltage was applied to the organic EL element, and the time (LT95, in hours) until the brightness reached 95% of its initial brightness was measured. In Table 1, the element lifetime is expressed as a relative value with Comparative Example 1 described later set to 100.

[0369] • Drive voltage At room temperature, using a DC constant current of 10mA / cm 2 The initial characteristics of organic EL elements are measured by driving.

[0370] Examples 2-5 As the main material for the first luminescent layer, the compound described in Table 1 was used instead of Inv-1. Otherwise, the organic EL element was fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 1.

[0371] Comparative Examples 1-2 As the main material for the first luminescent layer, the compound described in Table 1 was used instead of Inv-1. Otherwise, the organic EL element was fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 1.

[0372] [Table 1] .

[0373] Example 6 <Fabrication of Organic EL Components> Organic EL components are fabricated as follows.

[0374] A 25mm × 75mm × 1.1mm thick glass substrate (manufactured by Geomatics Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[0375] The cleaned glass substrate with transparent electrodes is mounted on the substrate support of the vacuum evaporation apparatus. First, compound HI-1 is evaporated to cover the transparent electrodes on the side where they are formed, and a hole injection layer with a thickness of 5 nm is formed into a film.

[0376] Compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 80 nm.

[0377] Compound EB-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[0378] On the second hole transport layer, compounds Inv-7 (host material) and BD-1 (dopant material) were co-deposited at a ratio of 2% by mass to form the first light-emitting layer with a thickness of 5 nm.

[0379] On the first luminescent layer, compound BH-2 (host material) and compound BD-1 (dopant material) are co-deposited in a ratio of 2% by mass to form a second luminescent layer with a thickness of 20 nm.

[0380] Compound HB-1 was deposited on the second luminescent layer to form the first electron transport layer with a thickness of 10 nm.

[0381] Compound ET-1 was deposited on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm.

[0382] LiF was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0383] Metallic Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0384] If we simply show the component configuration of the organic EL element of Example 5, it is as follows.

[0385] ITO(130) / HI-1(5) / HT-1(80) / EB-1(10) / Inv-7:BD-1(5:2%) / BH-2:BD-1(20:2%) / HB-1(10) / ET-1(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Additionally, the percentages in parentheses indicate the proportion (by mass) of the latter compound in that layer.

[0386] <Evaluation of Organic EL Components> The resulting organic EL devices were evaluated for drive voltage, external quantum efficiency (EQE), and device lifetime as follows. The results are shown in Table 2.

[0387] • Drive voltage At room temperature, using a DC constant current of 10mA / cm 2 The initial characteristics of organic EL elements are measured by driving.

[0388] • External quantum efficiency (EQE) For the fabricated organic EL devices, a current density of 10 mA / cm² was achieved. 2 A voltage was applied to the organic EL element, and the EL emission spectrum was measured using a CS-2000 spectroradiometer (manufactured by Conicaminodesk Ltd.). In Table 2, EQE represents the relative value when Comparative Example 3 described later is set to 100.

[0389] • Component lifespan At room temperature, a current density of 50 mA / cm 2 A voltage was applied to the organic EL element, and the time (LT95, in hours) until the brightness reached 95% of the initial brightness was measured. In Table 2, the element lifetime is expressed as a relative value with Comparative Example 3 described later set to 100.

[0390] Examples 7-10 As the main material for the first luminescent layer, the compound described in Table 2 was used instead of Inv-7. Otherwise, the organic EL element was fabricated and evaluated in the same manner as in Example 6. The results are shown in Table 2.

[0391] Comparative Example 3 As the main material for the first luminescent layer, the compound described in Table 2 was used instead of Inv-7. Otherwise, the organic EL element was fabricated and evaluated in the same manner as in Example 6. The results are shown in Table 2.

[0392] [Table 2] .

[0393] Example 11 <Fabrication of Organic EL Components> Organic EL components are fabricated as follows.

[0394] A 25mm × 75mm × 1.1mm thick glass substrate (manufactured by Geomatics Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[0395] The cleaned glass substrate with transparent electrodes is mounted on the substrate support of the vacuum evaporation apparatus. First, compounds HT-2 and HI-2 are co-evaporated at a ratio of 3% by mass to cover the transparent electrode on the side where the transparent electrode is formed, and a hole injection layer with a film thickness of 10 nm is formed.

[0396] Compound HT-2 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 85 nm.

[0397] Compound EB-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm.

[0398] On the second hole transport layer, compounds Inv-6 (host material) and BD-2 (dopant material) were co-deposited at a ratio of 2% by mass to form the first light-emitting layer with a thickness of 5 nm.

[0399] On the first luminescent layer, compound BH-3 (host material) and compound BD-2 (dopant material) were co-deposited at a ratio of 2% by mass to form a second luminescent layer with a thickness of 14 nm.

[0400] Compound HB-2 was deposited on the second luminescent layer to form the first electron transport layer with a thickness of 5 nm.

[0401] On the first electron transport layer, compounds ET-2 and Liq were co-deposited at a ratio of 50% by mass to form a second electron transport layer with a thickness of 31 nm.

[0402] Liq was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0403] Metallic Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0404] If we simply illustrate the component configuration of the organic EL element of Example 11, it would look like this.

[0405] ITO(130) / HT-2:HI-2(10:3%) / HT-2(85) / EB-2(5) / Inv-6:BD-2(5:2%) / BH-3:BD-2(14:2%) / HB-2(5) / ET-2:Liq(31:50%) / Liq(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Additionally, the percentages in parentheses indicate the proportion (by mass) of the latter compound in that layer.

[0406] <Evaluation of Organic EL Components> The driving voltage, external quantum efficiency (EQE), and device lifetime of the obtained organic EL devices were evaluated in the same manner as in Example 6. The results are shown in Table 3. In Table 3, EQE and device lifetime are relative values ​​with Comparative Example 4 described later set to 100.

[0407] Examples 12-16 As the main material for the first luminescent layer, the compound described in Table 3 was used instead of Inv-6. Otherwise, the organic EL element was fabricated and evaluated in the same manner as in Example 11. The results are shown in Table 3.

[0408] Comparative Examples 4-6 As the main material for the first luminescent layer, the compound described in Table 3 was used instead of Inv-6. Otherwise, the organic EL element was fabricated and evaluated in the same manner as in Example 11. The results are shown in Table 3.

[0409] [Table 3] .

[0410] <Compound Synthesis> (Synthesis Example 1) Synthesis of Inv-7 Synthesize Inv-7 using the following synthesis path.

[0411] [Chemistry 140] Under an argon atmosphere, intermediate 1-1 (benzo[b]naphtho[1,2-d]furan-2-yl trifluoromethanesulfonate: 10.0 g, 27.3 mmol) and intermediate 2-1 (4,4,5,5-tetramethyl-2-[( 2 H 11A mixture of [benzanthracene-7-yl]-1,3,2-dioxaborhexacyclopentane (9.97 g, 27.3 mmol), tris(dibenzylacetone)dipalladium(0) (0.49 g, 0.546 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl (SPhos) (0.89 g, 2.18 mmol), 2M sodium carbonate aqueous solution (34 mL), and 1,4-dioxane (136 mL) was refluxed at boiling point for 6 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to give 6.84 g of a white solid in 55% yield. As a result of mass spectrometry analysis, the obtained substance was identified as compound Inv-7, with a molecular weight of 455.60 and m / z = 456.

[0412] (Synthetic Examples 2-13) Synthesis of Inv-1, 3-6, 8-10, and 13-16 Except for changing the intermediates in Synthesis Example 1 to the compounds shown in Tables 4-5, the same method as in Synthesis Example 1 was used for the synthesis.

[0413] [Table 4] .

[0414] [Table 5] .

[0415] (Synthesis Example 14) Synthesis of Inv-2 Synthesize Inv-2 using the following synthesis path.

[0416] [Chemistry 141] Under an argon atmosphere, intermediate 1-2(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborhexacyclopentan-2-yl)-( 2 H9) Benzo[b]naphtho[2,3-d]furan: 10.0 g, 28.3 mmol), intermediate 2-2(12-bromo-7-( 2 H5) Phenyl ( 2 H 10A mixture of benzanthracene (11.3 g, 28.3 mmol), tris(dibenzylacetone)palladium(0) (0.51 g, 0.566 mmol), 2-dicyclohexylphosphine-2′-(N,N-dimethylamino)biphenyl (DavePhos: 0.89 g, 2.26 mmol), cesium carbonate (23.1 g, 70.8 mmol), 1,4-dioxane (115 mL), and water (25 mL) was refluxed at boiling point for 6 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and recrystallization to give 9.71 g of a white solid in 63% yield. As a result of mass spectrometry analysis, the obtained substance was identified as compound Inv-2, with a molecular weight of 544.78 and m / z = 545.

[0417] (Synthetic Examples 15-16) Synthesis of Inv-11-12 Except for changing the intermediates in Synthesis Example 14 to the compounds shown in Table 6, the same method as in Synthesis Example 14 was used for the synthesis.

[0418] [Table 6] .

[0419] The foregoing has described several embodiments and / or examples of the present invention in detail. However, those skilled in the art will readily apply many changes to these illustrative embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, these many changes are also included within the scope of the present invention.

[0420] All the documents described in this specification and the contents of the application that form the basis of the Paris Convention priority claim for this application are incorporated herein by reference.

Claims

1. The compound represented by any of the following formulas (1) to (3), [Chemistry 142] In equation (1), Ar1 is Aryl groups formed by the fusion of four or more monocyclic rings, either substituted or unsubstituted, or A monovalent heterocyclic group consisting of four or more monocyclic rings, fused together, with or without substitution; n1 is an integer from 0 to 3; When n1 is 0, (L1) n1 It is a single bond; When n1 is 2 or more, two or more L1s are connected in series; when n1 is 2 or more, two or more L1s can be the same or different. L1 is single bond, Substituted or unsubstituted arylene groups with 6 to 12 cyclic carbon atoms, or A divalent heterocyclic group, substituted or unsubstituted, with 5 to 50 cyclic atoms; When Ar1 is a substituted or unsubstituted pyrene group, R 15 and R 17 ~R 20 One of them represents (L1). n1 The key; When Ar1 is a group other than a substituted or unsubstituted pyrene group, R 15 ~R 20 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 11 ~R 20 Each is independently a hydrogen atom or a substituent R; In equation (2), Ar1, L1, and n1 are defined as in equation (1) above; When Ar1 is a substituted or unsubstituted pyrene group, R 25 ~R 27 and R 29 ~R 30 One of them represents (L1). n1 The key; When Ar1 is a group other than a substituted or unsubstituted pyrene group, R 25 ~R 30 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 21 ~R 30 Each is independently a hydrogen atom or a substituent R; In equation (3), Ar1, L1, and n1 are defined as in equation (1) above; R 35 ~R 40 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 31 ~R 40 Each is independently a hydrogen atom or a substituent R; Substituent R is Alkyl groups with 1 to 50 carbon atoms, whether substituted or unsubstituted Alkenes with 2 to 50 substituted or unsubstituted carbon atoms Alkyne groups with 2 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted; R 901 ~R 907 Each independently hydrogen atom, Alkyl groups with 1 to 50 carbon atoms, whether 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 Monovalent heterocyclic groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted; R 901 ~R 907 When there are more than two, more than two R 901 ~R 907 They can be the same or different.

2. The compound according to claim 1, wherein, Ar1 is a group represented by any of the following formulas (Ar-1) to (Ar-3). [Chemistry 143] In equation (Ar-1), By R a11 ~R a20 One or more groups of two or more adjacent elements are bonded together to form a substituted or unsubstituted monocyclic or fused ring. R that does not form the aforementioned monocyclic or fused ring a11 ~R a20 One of them represents (L1). n1 The bond, or one of the aforementioned cyclic atoms in a monocyclic or fused ring, is bonded to (L1) by a single bond. n1 Bonding; R that does not form the aforementioned monocyclic or fused ring and does not represent the aforementioned single bond a11 ~R a20 Each is independently a hydrogen atom or a substituent R; In equation (Ar-2), X a21 For O, S, N (R) a29 ), or C(R) a30 )2; By R a21 ~R a28 One or more groups of two or more adjacent elements are bonded together to form a substituted or unsubstituted monocyclic or fused ring. R that does not form the aforementioned monocyclic or fused ring a21 ~R a29 One of them represents (L1). n1 The key, or by R a21 ~R a28 One of the cyclic atoms in a monocyclic or fused ring formed by two or more adjacent atoms in a group is bonded to (L1) by a single bond. n1 Bonding; 2 Rs a30 They bond to each other to form substituted or unsubstituted monocyclic or fused rings, or do not form the aforementioned monocyclic or fused rings; R that does not form the aforementioned monocyclic or fused ring and does not represent the aforementioned single bond a21 ~R a30 Each is independently a hydrogen atom or a substituent R; 2 Rs a30 They can be the same or different; In equation (Ar-3), X a31 For O or S; By R a31 ~R a40 One or more groups of two or more adjacent elements are bonded together to form a substituted or unsubstituted monocyclic or fused ring. R that does not form the aforementioned monocyclic or fused ring a31 ~R a38 One of them represents (L1). n1 The bond, or one of the aforementioned cyclic atoms in a monocyclic or fused ring, is bonded to (L1) by a single bond. n1 Bonding; R that does not form the aforementioned monocyclic or fused ring and does not represent the aforementioned single bond a31 ~R a40 Each is independently a hydrogen atom or a substituent R; The substituent R is defined as in equations (1) to (3) above.

3. The compound according to claim 1 or 2, wherein, Ar1 is Substituted or unsubstituted benzo[anthracene] Substituted or unsubstituted pyrene, Substituted or unsubstituted triphenylene Substituted or unsubstituted bases Substituted or unsubstituted benzofluorene, Substituted or unsubstituted naphthobenzofuranyl, or Substituted or unsubstituted benzoxanthine group.

4. The compound according to any one of claims 1 to 3, wherein, Ar1 is Substituted or unsubstituted benzo[anthracene] Substituted or unsubstituted pyrene group, or Substituted or unsubstituted benzoxanthine group.

5. The compound according to any one of claims 1 to 4, wherein, L1 is a single bond.

6. The compound according to any one of claims 1 to 5, wherein, n1 is 0.

7. The compound according to any one of claims 1 to 6, wherein, Not indicating (L1) n1 The key of R 11 ~R 40 Each independently hydrogen atom, Alkyl groups with 1 to 10 carbon atoms, whether substituted or unsubstituted Substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms substituted or unsubstituted aryl groups with 6 to 10 cyclic carbon atoms, or Monovalent heterocyclic groups with 5 to 13 cyclic atoms, whether substituted or unsubstituted.

8. The compound according to any one of claims 1 to 7, wherein, Not indicating (L1) n1 The key of R 11 ~R 40 Each independently hydrogen atom, Substituted or unsubstituted phenyl, or Substituted or unsubstituted naphthyl groups.

9. The compound according to any one of claims 1 to 8, wherein, Not indicating (L1) n1 The key of R 11 ~R 40 It is a hydrogen atom.

10. The compound according to any one of claims 1 to 9, wherein, Ar1 has at least one deuterium atom.

11. The compound according to claim 1, wherein, The compound represented by any of the aforementioned formulas (1) to (3) is a compound represented by any of the following formulas (1-1) to (1-3), (2-1) to (2-3), and (3-1) to (3-3). [Chemistry 144] [Chemistry 145] [Chemistry 146] In equations (1-1)~(1-3), (2-1)~(2-3), and (3-1)~(3-3), n1, L1, R 11 ~R 40 As defined in equations (1) to (3) above; R 101 ~R 112 R 201 ~R 210 and R 301 ~R 310 One of them represents (L1). n1 The key; Not indicating (L1) n1 The key of R 101 ~R 112 R 201 ~R 210 and R 301 ~R 310 Each is independently a hydrogen atom or a substituent R; The substituent R is defined as in equations (1) to (3) above.

12. The compound according to claim 11, wherein, Not indicating (L1) n1 The key of R 101 ~R 112 R 201 ~R 210 and R 301 ~R 310 It is a hydrogen atom.

13. The compound according to claim 1, wherein, The compound represented by any of the aforementioned formulas (1) to (3) is a compound represented by any of the following formulas (1-11), (2-11), (2-12), and (2-21). [Chemistry 147] [Chemistry 148] In equations (1-11), (2-11), (2-12), and (2-21), n1, L1, and R... 11 ~R 14 R 16 ~R 20 R 21 ~R 24 and R 26 ~R 30 As defined in equations (1) to (3) above; R 101 ~R 112 and R 202 ~R 210 Each is independently a hydrogen atom or a substituent R; The substituent R is defined as in equations (1) to (3) above.

14. 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 aforementioned organic layers contains the compound according to any one of claims 1 to 13.

15. The organic electroluminescent element according to claim 14, comprising an anode, a light-emitting layer and a cathode in sequence, wherein at least one organic layer of the light-emitting layer comprises the aforementioned compound.

16. The organic electroluminescent element according to claim 15, wherein, The aforementioned light-emitting layer comprises a first layer and a second layer from the anode side, and the aforementioned first layer comprises the aforementioned compound.

17. An electronic device having an organic electroluminescent element according to any one of claims 14 to 16.

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