Compounds and organic electroluminescent elements using them

Abstract

The compound shown in formula (1) below.

Description

Technical Field

[0001] This invention relates to novel compounds and organic electroluminescent elements using the same. 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 conventional organic EL devices is not yet adequate. In order to improve device performance, the materials used in organic EL devices have been gradually improved (e.g., Patent Document 1), but further high performance is still required.

[0004] Existing technical documents Existing technical documents Patent documents Patent document 1: International Publication No. 2022 / 264827. Summary of the Invention

[0005] The purpose of this invention is to provide high-performance organic EL elements and compounds that enable such organic EL elements.

[0006] According to the present invention, the following compounds, etc., may be provided.

[0007] 1. The compound represented by the following formula (1).

[0008] [Chemistry 1] (In formula (1),) R1~R 11 Each independently hydrogen atom, or Aryl groups with 6 to 14 cyclic carbon atoms, substituted or unsubstituted.

[0009] R 21 ~R 34 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Substituted or unsubstituted cycloalkyl groups with 5 to 10 carbon atoms.

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

[0011] According to the present invention, high-performance organic EL elements and compounds that can realize such organic EL elements can be provided. Attached Figure Description

[0012] Figure 1 This is a diagram illustrating a schematic configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

[0013] [definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely, protium atom, deuterium atom and tritium atom.

[0014] In this specification, in the chemical structural formula, hydrogen atoms, i.e. protium atoms, deuterium atoms, or tritium atoms, are bonded at positions not explicitly indicated by symbols such as "R" or "D" representing deuterium atoms.

[0015] In this specification, the number of cyclic carbon atoms refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded together to form a cyclic structure (e.g., monocyclic compounds, fused-ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of cyclic carbon atoms. The term "number of cyclic carbon atoms" as used below is the same unless otherwise stated. For example, the number of cyclic carbon atoms in a benzene ring is 6, in a naphthalene ring it is 10, in a pyridine ring it is 5, and in a furan ring it is 4. Additionally, for example, the number of cyclic carbon atoms in 9,9-diphenylfluorenyl is 13, and in 9,9'-spirodifluorenyl it is 25.

[0016] Furthermore, when a benzene ring is substituent, for example, with an alkyl group, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in a benzene ring with a substituent alkyl group is 6. Similarly, when a naphthalene ring is substituent, for example, with an alkyl group, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in a naphthalene ring with a substituent alkyl group is 10.

[0017] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds) whose atoms are bonded to form a cyclic structure (e.g., monocyclic, fused-ring, and ring aggregates). Atoms that do not constitute a ring (e.g., hydrogen atoms that end the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Additionally, for example, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring bonded with hydrogen atoms or substituents is 10.

[0018] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon atoms numbering XX to YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, excluding the number of carbon atoms in substituents. Here, "YY" is greater than "XX", where "XX" refers to an integer greater than 1 and "YY" refers to an integer greater than 2.

[0019] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms in the ZZ group when it is unsubstituted, excluding the number of atoms in the substituent group when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1 and "YY" is an integer greater than or equal to 2.

[0020] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0021] In this specification, "unsubstituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0022] Furthermore, in this specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substitution" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0023] Substituents described in this specification The substituents described in this specification will be explained below.

[0024] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" as described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0025] 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.

[0026] Unless otherwise stated in this specification, the number of carbon atoms in "unsubstituted alkyl" as stated in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0027] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" specified in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0028] 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.

[0029] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted cycloalkyl" as described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0030] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0031] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0032] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylene" as described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0033] • "Substituted or unsubstituted aryl groups" As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls (specific example group G1A) and substituted aryls (specific example group G1B) etc. can be cited (here, the unsubstituted aryl refers to the case where the "substituted or unsubstituted aryl" is an "unsubstituted aryl", and the substituted aryl refers to the case where the "substituted or unsubstituted aryl" is a "substituted aryl"). In this specification, when only "aryl" is mentioned, it includes both "unsubstituted aryl" and "substituted aryl".

[0034] "Substituted aryl" means that one or more hydrogen atoms of the "unsubstituted aryl" are replaced by substituents. As the "substituted aryl", examples include groups in which one or more hydrogen atoms of the "unsubstituted aryl" in the following specific example group G1A are replaced by substituents, and examples of the substituted aryl in the following specific example group G1B etc. It should be noted that the examples of the "unsubstituted aryl" and the "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atoms bonded to the carbon atoms of the aryl itself in the "substituted aryl" in the following specific example group G1B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted aryl" in the following specific example group G1B are further replaced by substituents.

[0035] · Unsubstituted aryls (specific example group G1A): Phenyl, p - Biphenylyl, m - Biphenylyl, o - Biphenylyl, p - Terphenyl - 4 - yl, p - Terphenyl - 3 - yl, p - Terphenyl - 2 - yl, m - Terphenyl - 4 - yl, <000024]]m - Terphenyl - 3 - yl, m - Terphenyl - 2 - yl, o - Terphenyl - 4 - yl, o - Terphenyl - 3 - yl, o - Terphenyl - 2 - yl, 1 - Naphthyl, 2 - Naphthyl, Anthryl, Benzoanthryl, Phenanthryl, Benzo[a]phenanthryl, Phenalenyl, Pyrenyl, Chrysenyl, Benzo[c]chrysenyl, Triphenylenyl, Benzo[a]triphenylenyl, Tetracenyl,​ Pentaphenyl, Fluorine 9,9'-spirodifluorene, benzo[f]fluorene, Dibenzofluorene, Fluoranthene group, Benzofluoranthyl, Perylene, and A monovalent aryl group is derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-1) to (TEMP-15).

[0036] [Chemistry 2] [Chemistry 3] .

[0037] • Substituted aryl groups (specific example group G1B): o-Tolyl, m-Tolyl, p-Tolyl, p-Xylyl, m-Xylyl, o-xylyl, p-isopropylphenyl, m-Isopropylphenyl, o-isopropylphenyl, p-tert-butylphenyl, m-tert-butylphenyl, o-tert-butylphenyl, 3,4,5-Trimethylphenyl 9,9-Dimethylfluorenyl, 9,9-Diphenylfluorenyl 9,9-Bis(4-methylphenyl)fluorenyl, 9,9-Bis(4-isopropylphenyl)fluorenyl, 9,9-Bis(4-tert-butylphenyl)fluorenyl, cyanophenyl, Triphenylsilylphenyl Trimethylsilylphenyl Phenynaphthyl, Naphthylphenyl, and A group formed by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure shown in the aforementioned general formulas (TEMP-1) to (TEMP-15) with substituents.

[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, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group"). In this specification, when "heterocyclic group" is mentioned alone, it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

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

[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 formed by replacing one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) with substituents (specific example group G2B4).

[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, Phenazine group, 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, Benzothiophene (benzothio) Isobenzothiophene (isobenzophenylthio) dibenzothiophene (dibenzophenylthio) Naphthobenzothiophene (naphthobenzobenzyl) Benzothiazolyl, Benzisothiazolyl, phenothiazine group, Dinaphthothiophene (dinaphthophenylthio) Azadibenzothiophene (azadibenzophenylthio) diazadibenzothiophene (diazadibenzophenylthio) Azanaphthobenzothiophene (azanaphthobenzophenylthio) and Diazanaphthenebenzothiophene (diazanaphthenebenzothiophene).

[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] .

[0049] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y AEach can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0050] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the aforementioned general formulas (TEMP-16) to (TEMP-33) contains a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0051] • 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.

[0052] • 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].

[0053] • Heterocyclic groups containing sulfur atoms (specific example group G2B3): Phenyl dibenzothiophene, Methyldibenzothiophene, tert-butyldibenzothiophene, and The 1-valent residue of [9H-thioxanth-9,9'-[9H]fluorene].

[0054] • A group formed by replacing one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structures shown in the aforementioned general formulas (TEMP-16) to (TEMP-33) with substituents (specific example group G2B4): The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0055] • "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".

[0056] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by substituents. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkyl" (specific example group G3A) are replaced by substituents, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes straight-chain "unsubstituted alkyl" and branched "unsubstituted alkyl". It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples. The "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl" of specific example group G3B are further replaced by substituents.

[0057] • Unsubstituted alkyl groups (specific example group G3A): methyl, Ethyl, n-propyl, Isopropyl, n-Butyl, Isobutyl, sec-butyl, and tert-butyl.

[0058] • Substituted alkyl groups (specific example group G3B): Heptafluoropropyl (including isomers) Pentafluoroethyl, 2,2,2-Trifluoroethyl, and Trifluoromethyl

[0059] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group"). In this specification, when "alkenyl group" is mentioned alone, it includes both "unsubstituted alkenyl group" and "substituted alkenyl group".

[0060] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by substituents. Specific examples of "substituted alkenyl" include the substituents in the "unsubstituted alkenyl" group (specific example group G4A) and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples. The "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself are further replaced by substituents, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituents are further replaced by substituents.

[0061] • Unsubstituted alkenyl groups (specific example group G4A): vinyl, Allyl 1-Butenyl, 2-Butenyl, and 3-Butenyl.

[0062] • Substituted alkenyl groups (specific example group G4B): 1,3-Butadienyl, 1-Methylvinyl 1-Methylallyl, 1,1-Dimethylallyl, 2-Methylallyl, and 1,2-Dimethylallyl.

[0063] • "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".

[0064] "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.

[0065] • Unsubstituted alkynyl group (specific example group G5A): Acetylene group.

[0066] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl"). In this specification, when "cycloalkyl" is mentioned alone, it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0067] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by substituents. Specific examples of "substituted cycloalkyl" include groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" (specific example group G6A) are replaced by substituents, and examples of substituted cycloalkyl (specific example group G6B), etc. It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" of specific example group G6B are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" of specific example group G6B are further replaced by substituents.

[0068] • Unsubstituted cycloalkyl groups (specific example group G6A): Cyclopropyl Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Adamantyl, 2-Adamantyl, 1-Norbornel alkyl, and 2-Norbornel alkyl.

[0069] • Substituted cycloalkyl groups (specific example group G6B): 4-Methylcyclohexyl.

[0070] ·"-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).

[0071] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0072] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0073] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0074] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

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

[0076] In -Si(G1)(G2)(G2), the multiple G2s may be the same or different.

[0077] In -Si(G1)(G1)(G2), multiple G1s may be the same or different.

[0078] In -Si(G2)(G2)(G2), the multiple G2s may be the same or different.

[0079] In -Si(G3)(G3)(G3), the multiple G3s may be the same or different.

[0080] In -Si(G6)(G6)(G6), the multiple G6s may be the same or different.

[0081] ·"-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).

[0082] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0083] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0084] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0085] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0086] • "-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).

[0087] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0088] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0089] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0090] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0091] ·"-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).

[0092] in, G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0093] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0094] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0095] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0096] In -N(G1)(G1), multiple G1s may be the same or different.

[0097] In -N(G2)(G2), multiple G2s may be the same or different.

[0098] In -N(G3)(G3), multiple G3s may be the same or different.

[0099] 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.

[0100] • "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" are replaced by fluorine atoms (perfluoroalkyl). The number of carbon atoms in the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl" are replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl" are further replaced by substituents, and groups in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl" are further replaced by substituents. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in the aforementioned "alkyl" (specific example group G3) in which one or more hydrogen atoms are replaced by fluorine atoms.

[0101] • "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" is replaced by a halogen atom, and also includes groups in which all hydrogen atoms bonded to the carbon atom of the alkyl group constituting the "substituted or unsubstituted alkyl" are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of the "haloalkyl" are replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl" are further replaced by a substituent, and groups in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl" are further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in the aforementioned "alkyl" (specific example group G3) in which one or more hydrogen atoms are replaced by halogen atoms. Sometimes haloalkyl is referred to as alkyl halide.

[0102] • "Substituted or unsubstituted alkoxy groups" As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, there is a group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.

[0103] • "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.

[0104] • "Substituted or unsubstituted aryloxy groups" As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of cyclic carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0105] • "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.

[0106] • "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.

[0107] • "Substituted or unsubstituted aralkyl groups" As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is a type of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" replaced by "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50 unless otherwise specified in this specification, preferably 7 to 30, and more preferably 7 to 18.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] In this specification, the carbazoyl group, unless otherwise specified herein, refers to any of the following groups.

[0112] [Chemistry 6] .

[0113] In this specification, (9-phenyl)carbazolyl refers to any of the following groups unless otherwise specified in this specification.

[0114] [Chemistry 7] .

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

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

[0117] [Chemistry 8] .

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

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

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

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

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

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

[0124] [Chemistry 9] [Chemistry 10] .

[0125] In the aforementioned general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0126] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * indicates the bonding site.

[0127] [Chemistry 11] .

[0128] In the aforementioned general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0129] Formulas Q9 and Q 10 They can form rings by bonding with each other through single bonds.

[0130] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * indicates the bonding site.

[0131] [Chemistry 12] .

[0132] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0133] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * indicates the bonding site.

[0134] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0135] [Chemistry 13] [Chemistry 14] [Chemistry 15] .

[0136] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0137] [Chemistry 16] [Chemistry 17] [Chemistry 18] [Chemistry 19] .

[0138] In the aforementioned general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0139] The above is an explanation of the substituents described in this specification.

[0140] • "Cases where bonds form rings" In this specification, the phrase "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together, forming a substituted or unsubstituted fused ring by bonding together, or not bonding together" refers to the following: forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together; forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together; and not bonding one or more groups of two or more adjacent elements together.

[0141] The following description addresses the cases of "a substituted or unsubstituted monocyclic ring formed by the mutual bonding of one or more groups of two or more adjacent elements" and "a substituted or unsubstituted fused ring formed by the mutual bonding of one or more groups of two or more adjacent elements" (hereinafter, these cases are sometimes collectively referred to as "the case of forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0142] [Chemistry 20] .

[0143] 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 R929 With R 921 The group.

[0144] The phrase "one or more groups" refers to the fact that two or more groups consisting of two or more adjacent elements can simultaneously form a loop. For example, R 921 With R 922 They bond together to form a ring Q A And at the same time R 925 With R 926 They bond together to form a ring Q B In the case of the anthracene compound represented by the aforementioned general formula (TEMP-103), the anthracene compound is represented by the following general formula (TEMP-104).

[0145] [Chemistry 21] .

[0146] The case of rings formed by "groups consisting of two or more adjacent elements" includes not only the case of group bonding consisting of "two" adjacent elements as in the previous example, but also the case of group bonding consisting of "three or more" adjacent elements. For example, it refers to R. 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923 When the groups of elements Q bond together to form a ring, fused together to form an anthracene matrix, the anthracene compound represented by the aforementioned general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .

[0147] [Chemistry 22] .

[0148] The formed "monocyclic ring" or "fused ring," as a structure consisting only of rings, can be a saturated ring or an unsaturated ring. Even when a "monocyclic ring" or "fused ring" is formed from "one of the groups consisting of two adjacent rings," the "monocyclic ring" or "fused ring" can form a saturated ring or an unsaturated ring. For example, the ring Q formed in the aforementioned general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the aforementioned general formula (TEMP-105) A and ring Q CIt 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 Fusing together to form fused rings. The ring Q of the aforementioned general formula (TEMP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the aforementioned general formula (TEMP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0149] "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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] "Ring formation" refers to the formation of a ring solely from multiple atoms of the parent skeleton, or from multiple atoms of the parent skeleton combined with one or more arbitrary atoms. For example, R shown in the aforementioned general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The bonded anthracene framework consists of carbon atoms and rings formed with one or more arbitrary atoms. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the carbon atoms of the bonded anthracene skeleton form a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The resulting ring is a benzene ring.

[0154] 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.

[0155] 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.

[0156] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0157] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0158] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0159] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0160] Unless otherwise stated in this specification, the preferred form is an unsaturated ring consisting of multiple atoms of a parent skeleton and at least 15 atoms selected from carbon, nitrogen, oxygen and sulfur atoms bonded together, forming a substituted or unsubstituted monocyclic ring.

[0161] 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.

[0162] 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.

[0163] 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").

[0164] 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.

[0165] R 901 When there are more than two, more than two R 901 They are the same or different. R 902 When there are more than two, more than two R 902 They are the same or different. R 903 When there are more than two, more than two R 903They are the same or different. R 904 When there are more than two, more than two R 904 They are the same or different. R 905 When there are more than two, more than two R 905 They are the same or different. R 906 When there are more than two, more than two R 906 They are the same or different. R 907 When there are more than two, more than two R 907 They are the same or different.

[0166] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from groups including: Alkyl groups with 1 to 50 carbon atoms aryl groups with 6 to 50 carbon atoms in the ring, and Heterocyclic groups with 5 to 50 cyclic atoms.

[0167] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from groups including: Alkyl groups with 1 to 18 carbon atoms aryl groups with 6 to 18 carbon atoms in the ring, and Heterocyclic groups with 5 to 18 cyclic atoms.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] In this specification, the numerical range represented by "AA~BB" refers to the range that includes the value AA listed before "AA~BB" as the lower limit and the value BB listed after "AA~BB" as the upper limit.

[0172] [New Compound] One aspect of the present invention relates to a compound represented by formula (1) described below.

[0173] The compounds involved in one aspect of the present invention can improve the performance of organic EL devices when used. For example, using the compounds involved in one aspect of the present invention can provide organic EL devices with low drive voltage and excellent external quantum efficiency.

[0174] [The compound shown in formula (1)] One aspect of the present invention relates to a compound as shown in formula (1).

[0175] [Chemistry 23] (In formula (1),) R1~R 11 Each independently hydrogen atom, or Aryl groups with 6 to 14 cyclic carbon atoms, substituted or unsubstituted.

[0176] R 21 ~R 34 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Substituted or unsubstituted cycloalkyl groups with 5 to 10 carbon atoms.

[0177] From R1~R 11 Two or more adjacent groups are not bonded to each other and do not form substituted or unsubstituted monocyclic or fused rings.

[0178] In one implementation, R1~R 10 It is a hydrogen atom.

[0179] In one implementation, R 11 It is an aryl group with 6 to 14 cyclic carbon atoms, either substituted or unsubstituted.

[0180] In one implementation, R 11 It can be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0181] In one implementation, R 11 It is a hydrogen atom.

[0182] By R 21 ~R 34 Two or more adjacent groups are not bonded to each other and do not form substituted or unsubstituted monocyclic or fused rings.

[0183] In one implementation, R 21 ~R30 It is a hydrogen atom.

[0184] In one implementation, R 31 ~R 34 It is a hydrogen atom.

[0185] In one embodiment, the compound represented by the aforementioned formula (1) is any one of the following formulas (1-1) to (1-4).

[0186] [Chemistry 24] [Chemistry 25] (In equations (1-1) to (1-4), R1~R 10 and R 21 ~R 34 As defined in equation (1) above.

[0187] R 111 ~R 115 R 121 ~R 127 and R 131 ~R 137 Each independently selected hydrogen atom, Alkyl groups having 1 to 6 carbon atoms (preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or tert-butyl). Haloalkyl groups having 1 to 6 carbon atoms (preferably trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, or 1,1,1,3,3,3-hexafluoroisopropyl). Alkenyl groups (preferably vinyl or propenyl) with 2 to 6 carbon atoms Cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, or adamantyl). Halogen atoms (preferably fluorine, chlorine, or bromine atoms), cyano, and An aryl group (preferably phenyl, naphthyl, biphenyl, or phenanthrene) with 6 to 14 carbon atoms (preferably 6 to 13, more preferably 6 to 12, and even more preferably 6 to 10). In one embodiment, the compound represented by the aforementioned formula (1) is any one of the following formulas (1-11) to (1-14).

[0188] [Chemistry 26] [Chemistry 27] (In equations (1-11)~(1-14), R1~R 10 R 111 ~R 115 R 121 ~R 127 and R 131 ~R 137 As defined in equations (1-1) to (1-4) above. In one implementation, R 111 ~R 115 R 121 ~R 127 and R 131 ~R 137 It is a hydrogen atom.

[0189] In one embodiment, the alkyl group having 1 to 6 carbon atoms in formula (1) is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, or n-hexyl.

[0190] In one embodiment, the cycloalkyl group with 5 to 10 cyclic carbon atoms in formula (1) is cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, or adamantyl.

[0191] In one embodiment, the aryl group with 6 to 14 cyclic carbon atoms in formula (1) is phenyl, naphthyl, biphenyl, fluorenyl, or phenanthryl.

[0192] In one embodiment, the substituted aryl group with 6 to 14 cyclic carbon atoms in formula (1) is terphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, naphthylphenyl, or phenylnaphthyl.

[0193] In one embodiment, the substituents in formula (1), referred to as "substituted or unsubstituted", are selected from... Alkyl groups having 1 to 6 carbon atoms (preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or tert-butyl). Haloalkyl groups having 1 to 6 carbon atoms (preferably trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, or 1,1,1,3,3,3-hexafluoroisopropyl). Alkenyl groups (preferably vinyl or propenyl) with 2 to 6 carbon atoms Cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, or adamantyl). Halogen atoms (preferably fluorine, chlorine, or bromine atoms), cyano, and The aryl group (preferably phenyl, naphthyl, biphenyl, or phenanthrene) has 6 to 14 carbon atoms (preferably 6 to 13, more preferably 6 to 12, and even more preferably 6 to 10).

[0194] The compound shown in formula (1) can be synthesized according to the examples by using known alternative reactions and starting materials consistent with the target compound.

[0195] The following describes specific examples of compounds involved in one aspect of the present invention, but these are merely illustrative examples, and the compounds involved in one aspect of the present invention are not limited to the specific examples described below.

[0196] [Chemistry 28] .

[0197] 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 electron transport region of organic EL elements.

[0198] [Organic EL Components] An organic EL element relating to one aspect of the present invention will be described.

[0199] 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.

[0200] One aspect of the present invention relates to an organic EL element that, by having the above-described configuration, can improve performance.

[0201] Reference Figure 1 This invention describes the general configuration of an organic EL element according to one aspect of the present invention.

[0202] In one embodiment, an organic EL element 1 according to one aspect of the present invention has: a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 located between the anode 3 and the light-emitting layer 5, and an organic layer 6 located between the light-emitting layer 5 and the cathode 10.

[0203] Organic layer 4 and organic layer 6 can each be a single layer, or they can be formed by multiple layers.

[0204] In one embodiment, an organic EL element according to one aspect of the present invention sequentially comprises an anode, a light-emitting layer, an electron transport region, and a cathode, wherein at least one layer in the aforementioned electron transport region comprises a compound according to one aspect of the present invention.

[0205] (Electronic transmission area) The electron transport region is a collective term for one or more layers disposed between the light-emitting layer and the cathode. For example, the electron transport region, starting from the light-emitting layer side, is composed of layers referred to later as a hole-blocking layer, an electron transport layer, and an electron injection layer. It can be a stacked structure containing all of these layers, or it can be composed of only a portion of these layers. Furthermore, for each of the above layers, two or more types of layers can be used; for example, two different electron transport layers can be stacked together.

[0206] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0207] In one embodiment, the aforementioned electron transport region has at least a first layer (also referred to as a "hole blocking layer" or "first electron transport layer") and a second layer (also referred to as an "electron transport layer" or "second electron transport layer") sequentially from the light-emitting layer side. The aforementioned second layer contains compounds involved in one aspect of the present invention.

[0208] In one embodiment, the aforementioned second layer substantially contains only the compounds involved in one aspect of the present invention.

[0209] "Substantially containing only the compound involved in one aspect of the invention" means that the second layer contains no other components at all, or contains only trace amounts of other components to the extent that they do not impair the effects of the invention. For example, this state is characterized by the presence of other components as unavoidable impurities.

[0210] (Other components of organic EL elements) 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, and conventionally known materials and elements may be used as long as the effects of the present invention are not impaired.

[0211] As a representative component configuration of this organic EL element, an example can be shown that the following structure is stacked on a substrate. (1) Anode / Light-emitting layer / Electron transport region / Cathode (2) Anode / Hole transport region / Light-emitting layer / Electron transport region / Cathode (“ / ” indicates that adjacent layers are stacked.)

[0212] (hole transport region) The hole transport region is a collective term for one or more layers disposed between the anode and the light-emitting layer. For example, from the light-emitting layer side, the hole transport region is composed of layers referred to later as an electron blocking layer, a hole transport layer, and a hole injection layer. It can be a stacked structure containing all of these layers, or it can be composed of only a portion of these layers. Furthermore, for each of the above layers, two or more types of layers can be used; for example, two different hole transport layers can be stacked together.

[0213] Each layer can be formed using only one material, or it can be formed using two or more materials.

[0214] The following describes the component structure and materials constituting each layer of an organic EL element according to one aspect of the present invention.

[0215] (Substrate) The substrate serves as a support for the light-emitting element. Materials such as glass, quartz, and plastic can be used as substrates. Flexible substrates can also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate or polyvinyl chloride.

[0216] (anode) The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples include indium tin oxide (ITO), indium zinc oxide, silicon- or silicon-oxide-containing indium tin oxide, zinc oxide-containing indium oxide, tungsten oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride).

[0217] (hole injection layer) A hole injection layer is a layer containing a substance with high hole injection capability. Substances with high hole injection capability 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, electron-withdrawing (acceptor) compounds, or polymers (oligomers, dendritic macromolecules, polymers, etc.).

[0218] (Hole transport layer) The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used. If the substance has higher hole transport capacity than electron transport capacity, substances other than these can also be used. It should be noted that the layer containing the substance with high hole transport capacity can be not only a single layer, but also a layer formed by stacking two or more layers containing the above-mentioned substances.

[0219] (The object material of the light-emitting layer) The luminescent layer is a layer containing a highly luminescent substance, and various materials can be used. For example, fluorescent compounds that emit light and phosphorescent compounds that emit light can be used as highly luminescent substances. Fluorescent compounds are compounds that emit light from a singlet excited state, while phosphorescent compounds are compounds that emit light from a triplet excited state.

[0220] 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.

[0221] 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.

[0222] (Main material of the light-emitting layer) The luminescent layer can be configured such that the highly luminescent substance (guest material) is dispersed in other substances (host material). Various substances can be used as the substance for dispersing the highly luminescent substance, but it is preferable to use a substance with a higher lowest empty orbital energy level (LUMO level) and a lower highest occupied orbital energy level (HOMO level) compared to the highly luminescent substance.

[0223] 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.

[0224] (Electron transport layer) The electron transport layer is a layer containing substances with high electron transport properties. In addition to the compounds shown in the aforementioned formula (1), the following can be used in the electron transport layer: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymeric compounds.

[0225] (Electron injection layer) The electron injection layer is a layer containing materials with high electron injection capacity. In the electron injection layer, compounds that can be used in the aforementioned electron transport layer, such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium 8-hydroxyquinoline (Liq), and other metal complex compounds, as well as lithium oxides (LiO), can be used. x Alkali metals, alkaline earth metals, or their compounds, etc.

[0226] (cathode) The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[0227] (Electron blocking layer, hole blocking layer, exciton blocking layer) Electron blocking layers, hole blocking layers, exciton (triple state) blocking layers, etc., can be set adjacent to the light-emitting layer.

[0228] 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.

[0229] In one embodiment of the organic EL element of the present invention, the method for forming each layer is not particularly limited. Formation methods based on conventionally known methods such as vacuum evaporation and spin coating can be used. Each layer, including the light-emitting layer, can be formed by known methods such as vacuum evaporation, molecular beam evaporation (MBE), or coating methods based on solutions dissolved in solvents, such as immersion coating, spin coating, casting, rod coating, and roll coating.

[0230] In one embodiment of the organic EL element of the present invention, the film thickness of each layer is not particularly limited. Generally, in order to suppress defects such as pinholes, suppress the applied voltage to a low level, and achieve good luminous efficiency, the thickness is usually preferred to be in the range of several nm to 1 μm.

[0231] One embodiment of the electronic device of the present invention includes the aforementioned organic electroluminescent element. Specific examples of the electronic device include display components such as organic EL panel assemblies; display devices for televisions, mobile phones, smartphones, personal computers, etc.; and light-emitting devices for lighting and vehicle lamps. Example

[0232] <Compound> The compound of formula (1) used in the manufacture of the organic EL element of Example 1 is shown below.

[0233] [Chemistry 29] The compounds used in the manufacture of the organic EL element of Comparative Example 1 are shown below.

[0234] [Chemistry 30] The structures of other compounds used in the manufacture of the organic EL elements of Example 1 and Comparative Example 1 are shown below.

[0235] [Chemistry 31] .

[0236] Example 1 <Fabrication of Organic EL Components> Organic EL elements are fabricated as described below.

[0237] A glass substrate (manufactured by Geomatics Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. This resulted in an ITO film thickness of 130nm.

[0238] The cleaned glass substrate with transparent electrodes is mounted on the substrate support of the vacuum evaporation apparatus. First, on the side where the transparent electrodes are formed, compounds HT-1 and HI-1 are co-evaporated to cover the transparent electrodes, so that the proportion of compound HI-1 reaches 3% by mass, forming a first hole transport layer with a film thickness of 10 nm.

[0239] Compound HT-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 77.5 nm.

[0240] Compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer with a thickness of 7.5 nm.

[0241] On the third hole transport layer, compounds BH-1 (host material), BH-2 (host material), and BD-1 (dopant material) were co-deposited with a ratio of 39% by mass of compound BH-2 and a ratio of 2% by mass of compound BD-1 to form a light-emitting layer with a film thickness of 20 nm.

[0242] Compound HBL-1 was deposited on the luminescent layer to form the first electron transport layer with a thickness of 5 nm.

[0243] On the first electron transport layer, compound ET-1 and lithium 8-hydroxyquinoline (Liq) were co-deposited at a ratio of 33% by mass to form a second electron transport layer with a thickness of 25 nm.

[0244] Metal Yb is deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[0245] Metallic Al was deposited on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0246] The component structure of the organic EL element in Example 1 is briefly shown below. ITO(130) / HT-1:HI-1(10:3%) / HT-1(77.5) / EBL-1(7.5) / BH-1:BH-2:BD-1(20:39%:2%) / HBL-1(5) / ET-1:Liq(25:33%) / Yb(1) / Al(50) The numbers in parentheses indicate the film thickness (in nm). Additionally, the percentage figures within parentheses indicate the proportion (mass%) of the latter compound in that layer. There are two percentage figures within parentheses, representing the proportion (mass%) of the second and third compounds in that layer, respectively.

[0247] <Evaluation of Organic EL Components> • Drive voltage At room temperature, with a constant DC current of 10mA / cm 2 The initial characteristics of the organic EL element were determined. The results are shown in Table 1.

[0248] External quantum efficiency (EQE) For the fabricated organic EL devices, to achieve a current density of 10 mA / cm² 2 A voltage (in V) was applied to the organic EL element, and the EL emission spectrum was measured using a CS-2000 spectrophotometer (manufactured by Conicaminodesk Ltd.). The results are shown in Table 1.

[0249] Comparative Example 1 Instead of compound HBL-1, the compounds described in Table 1 were used, and organic EL elements were fabricated and evaluated using the same method as in Example 1. The results are shown in Table 1.

[0250] [Table 1] .

[0251] <Compound Synthesis> (Synthetic Example 1) Synthesis of HBL-1 HBL-1 was synthesized using the following synthetic route.

[0252] [Chemistry 32] 12-Bromo-7-phenyltetraphene (8.0 g), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1,3,5-triazine (9.1 g), Pd2(dba)3 (0.19 g), and S-Phos (0.3 g) were added to a flask. After purging the flask with argon, 1,4-dioxacyclohexane (100 mL) and sodium carbonate aqueous solution (2 M, 21 mL) were added. The mixture was heated under reflux for 26 hours with stirring. The solvent was distilled off, and the crude product was purified by silica gel chromatography and washed with toluene to give HBL-1 as a white solid (11.0 g, yield 86%).

[0253] The mass spectrometry analysis showed a molecular weight of 611.75 and an m / e ratio of 612, identifying it as the target analyte.

[0254] (Synthetic Example 2) Synthesis of HBL-2 HBL-2 ​​was synthesized using the following synthetic route.

[0255] [Chemistry 33] Instead of 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1,3,5-triazine, 2,4-bis(phenyl-d5)-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1,3,5-triazine was used. Otherwise, the same procedures as in Synthesis Example 1 were performed to obtain HBL-2 ​​in the form of a white solid (3.9 g, 83% yield).

[0256] The mass spectrometry analysis results showed a molecular weight of 621.81 and an m / e ratio of 622, identifying it as the target analyte.

[0257] 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.

[0258] All the documents described in this specification and the contents of the application that form the basis of this application based on the priority of the Paris Convention are hereby incorporated into this application.

Claims

1. The compound represented by formula (1) below, [Chemistry 34] In equation (1), R1~R 11 Each independently hydrogen atom, or Aryl groups with 6 to 14 cyclic carbon atoms, substituted or unsubstituted. R 21 ~R 34 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, or Cycloalkyl groups with 5 to 10 carbon atoms, substituted or unsubstituted.

2. The compound according to claim 1, wherein, R 11 It is an aryl group with 6 to 14 cyclic carbon atoms, either substituted or unsubstituted.

3. The compound according to claim 1 or 2, wherein, R 11 It can be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

4. The compound according to claim 1, wherein it is represented by any one of the following formulas (1-1) to (1-4), [Chemistry 35] [Chemistry 36] In equations (1-1) to (1-4), R1 to R 10 and R 21 ~R 34 As defined in equation (1) above, R 111 ~R 115 R 121 ~R 127 and R 131 ~R 137 Each independently selected hydrogen atom, Alkyl groups with 1 to 6 carbon atoms Alkenes with 2-6 carbon atoms Cycloalkyl groups with 5-10 carbon atoms Halogen atoms, cyano, and Aryl groups with 6 to 14 carbon atoms forming a ring.

5. The compound according to claim 4, wherein it is represented by any one of the following formulas (1-11) to (1-14), [Chemistry 37] [Chemistry 38] In equations (1-11) to (1-14), R1 to R 10 R 111 ~R 115 R 121 ~R 127 and R 131 ~R 137 As defined in equations (1-1) to (1-4) above.

6. The compound according to claim 4 or 5, wherein, R 111 ~R 115 R 121 ~R 127 and R 131 ~R 137 It is a hydrogen atom.

7. The compound according to any one of claims 1 to 6, wherein, R 21 ~R 30 It is a hydrogen atom.

8. The compound according to any one of claims 1 to 7, wherein, R 31 ~R 34 It is a hydrogen atom.

9. The compound according to any one of claims 1 to 8, wherein, R1~R 10 It is a hydrogen atom.

10. 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 according to any one of claims 1 to 9.

11. The organic electroluminescent element according to claim 10, wherein, It comprises, in sequence, an anode, a light-emitting layer, an electron transport region, and a cathode, wherein at least one layer of the organic layer in the aforementioned electron transport region comprises the aforementioned compound.

12. The organic electroluminescent element according to claim 11, wherein, The aforementioned electron transport region has at least a first layer and a second layer sequentially from the aforementioned light-emitting layer side. The aforementioned first layer contains the aforementioned compound.

13. The organic electroluminescent element according to claim 11 or 12, wherein, The aforementioned electron transport region has at least a first layer and a second layer sequentially from the aforementioned light-emitting layer side. The aforementioned second layer contains the aforementioned compound.

14. The organic electroluminescent element according to any one of claims 11 to 13, wherein, There is a hole transport region between the aforementioned anode and the aforementioned light-emitting layer.

15. An electronic device comprising the organic electroluminescent element according to any one of claims 10 to 14.

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