Compounds, organic electroluminescent elements, and electronic devices

Abstract

To provide a compound that can improve the lifespan of an organic electroluminescent element, and to provide an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element. [Solution] A compound represented by the following general formula (1). TIFF2026098157000179.tif58159 Ring A x ring B is represented by the general formula (1A-1) or (1A-2). x This is a ring represented by the general formula (1B-1).

Description

[Technical Field]

[0001] The present invention relates to compounds, organic electroluminescent elements, and electronic devices. [Background technology]

[0002] Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays for mobile phones and televisions. When a voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical laws of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%. Examples of performance characteristics of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. For example, Patent Documents 1 and 2 describe studies aimed at improving the performance of organic EL elements. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Korean Published Patent Publication No. 10-2012-0116884 [Patent Document 2] Japanese Patent Publication No. 2019-169618 [Overview of the project] [Problems that the invention aims to solve]

[0004] The object of the present invention is to provide a compound that can improve the lifespan of an organic electroluminescent element, and to provide an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element. [Means for solving the problem]

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

[0006] [ka]

[0007] (In the above general formula (1), A set consisting of R1 and R2, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R1 and R2, which do not form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted fused ring, are each independently: Substituted or unsubstituted alkyl groups with 1 to 4 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Ring A X This is a ring represented by the general formula (1A-1) or (1A-2), The ring represented by the general formula (1A-1) above is condensed with ring Cx at position a, The ring represented by the general formula (1A-2) above is condensed with ring Cx at position b or c, Ring B X This is a ring represented by the general formula (1B-1), The ring represented by the general formula (1B-1) is condensed with ring Cx at positions d, e, f, or g. The ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1) each independently have one or more substituents represented by the following general formula (11) attached to them, or they do not have any substituents attached. At least one of the rings represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1) has one or more aryl groups Ar1 bonded to it. Ar1 is Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, A substituted or unsubstituted benzofluoranthenyl group, (It is a substituted or unsubstituted perilenyl group.)

[0008] [ka]

[0009] (In the above general formula (11), n 11 is 0, 1, 2, or 3, L 11 teeth, Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, Substituted or unsubstituted benzofluoranthenyl groups, and A divalent arylene group derived by removing one hydrogen atom from the aryl ring of either a substituted or unsubstituted perilen group, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, L 11 The heterocyclic group includes at least one atom selected from the group consisting of oxygen, sulfur, silicon, phosphorus, and boron as a heteroatom. When n11 is 0, L 11 This represents a single bond, Ar 11 teeth, Is it a hydrogen atom? Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, A substituted or unsubstituted benzofluoranthenyl group, Either a substituted or unsubstituted perilenyl group, These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Ar 11 The heterocyclic group includes at least one atom selected from the group consisting of oxygen, sulfur, silicon, phosphorus, and boron as a heteroatom. * indicates the bond location.

[0010] According to one aspect of the present invention, an organic electroluminescent element is provided that contains a compound according to one aspect of the present invention as a first compound.

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

[0012] According to one aspect of the present invention, a compound that can improve the lifespan of an organic electroluminescent element, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element can be provided. [Brief explanation of the drawing]

[0013] [Figure 1] This figure shows a schematic configuration of an example of an organic electroluminescent element according to one embodiment of the present invention. [Figure 2] This figure shows a schematic configuration of another example of an organic electroluminescent element according to one embodiment of the present invention. [Modes for carrying out the invention]

[0014] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0015] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.

[0016] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.

[0017] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

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

[0019] In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" means that "atom count XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more.

[0020] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0021] "Substituents as described herein" The substituents described herein will be explained below.

[0022] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

[0023] • "substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Examples Group G1) include the following unsubstituted aryl groups (Specific Examples Group G1A) and substituted aryl groups (Specific Examples Group G1B), etc. (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the groups in which one or more hydrogen atoms of an "unsubstituted aryl group" in specific example group G1A below are replaced by substituents, and the examples of substituted aryl groups in specific example group G1B below. Note that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in specific example group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted aryl group" in specific example group G1B below are further replaced by substituents.

[0024] • Unsubstituted aryl groups (specific examples group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, anthryl group, Benzoantryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perilenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0025] [ka]

[0026] [ka]

[0027] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.

[0028] • "Substitutable or unsubstituted heterocyclic groups" The “heterocyclic group” as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic group" as described herein is either a monocyclic group or a fused-cyclic group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples 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, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "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 groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.

[0029] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

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

[0031] • Unsubstituted heterocyclic groups containing a nitrogen atom (specific examples group G2A1): Pyrrolyl group, imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, pyrazinyl group, Triazinyl group, Indolyl group, isoindolyl group, indolidinyl group, Quinolidinyl group, quinolyl group, Isoquinolyl group, cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenantridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, Phenoxadinyl group, Phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0032] • Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): Frill group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0033] • Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): Thienyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzoisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazaazadibenzothiophenyl group (diazaazadibenzothienyl group), Azananofbenzothiophenyl group (azananofbenzothienyl group), and Diazaazananofbenzothiophenyl group (diazaazananofbenzothienyl group).

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

[0035]

Chemical formula

[0036]

Chemical formula

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

[0038] · A substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-Phenyl)carbazolyl group, (9-Biphenylyl)carbazolyl group, (9-Phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, Diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methyl benzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, Phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0039] • Heterocyclic groups with substitutions containing an oxygen atom (Specific examples group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0040] • Heterocyclic groups with substitutions containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0041] • Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):

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

[0043] • "Substituted or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group.") Hereafter, "alkyl group" simply refers to both "unsubstituted alkyl groups" and "substituted alkyl groups." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the groups in which one or more hydrogen atoms in the "unsubstituted alkyl groups" (specific example group G3A) below are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a linear alkyl group. Therefore, "unsubstituted alkyl groups" include both linear "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups". The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents.

[0044] • Unsubstituted alkyl groups (specific examples group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

[0045] · Substituted alkyl group (specific example group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-Trifluoroethyl group, and Trifluoromethyl group.

[0046] · "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when simply referring to an "alkenyl group", it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group". The "substituted alkenyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced by substituents. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl groups" (specific example group G4A) have substituents, and examples of substituted alkenyl groups (specific example group G4B), etc. Note that the examples of the "unsubstituted alkenyl group" and the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in this specification includes groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents.

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

[0048] • Substitutive alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0049] • "Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) are replaced by substituents.

[0050] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group

[0051] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B), etc. (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by a substituent. Specific examples of "substituted cycloalkyl groups" include the groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced by a substituent.

[0052] • Unsubstituted cycloalkyl groups (specific examples group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0053] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0054] · "-Si(R 901 )(R 902 )(R 903 ) represented by the base -Si(R 901 )(R 902 )(R 903 ) Examples of the base represented by (Example Group G7) are: -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) Here are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from one another. In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from one another. In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from one another.

[0055] ·「-O-(R 904 ) represented by the base The following information pertains to the -O-(R904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0056] · "-S-(R 905 ) represented by the base The following information pertains to the -S-(R 905 ) Examples of the base represented by (example group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0057] · "-N(R 906 )(R 907 ) represented by the base -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), the multiple G6s are either identical or different from one another.

[0058] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0059] • "Substituted or unsubstituted fluoroalkyl groups" The terms "substituted or unsubstituted fluoroalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The terms "substituted fluoroalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include the example of a group in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0060] • "Substituted or unsubstituted haloalkyl groups" The terms "substituted or unsubstituted haloalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The terms "substituted haloalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halogens.

[0061] • "Substituted or unsubstituted alkoxy groups" A specific example of a "substituted or unsubstituted alkoxy group" as described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0062] • "substituted or unsubstituted alkylthio groups" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0063] • "Substituted or unsubstituted aryloxy groups" A specific example of a "substituted or unsubstituted aryloxy group" as described herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0064] • "Substituted or unsubstituted arylthio groups" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0065] • "Substituted or unsubstituted trialkylsilyl groups" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either identical or different from one another. Unless otherwise specified herein, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

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

[0067] Unless otherwise specified herein, the substituted or unsubstituted aryl groups are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[0068] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0069] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0070] [ka]

[0071] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0072] [ka]

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

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

[0075] [ka]

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

[0077] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0078] • "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein 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 the "substituted or unsubstituted arylene group" (Specific Examples Group G12) include the divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.

[0079] • "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic groups” described herein refer to divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described above. Specific examples of “substituted or unsubstituted divalent heterocyclic groups” (Specific Examples Group G13) include the divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described in Specific Examples Group G2.

[0080] • "Substituted or unsubstituted alkylene groups" Unless otherwise specified, the "substituted or unsubstituted alkylene groups" described herein are divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described above. Specific examples of "substituted or unsubstituted alkylene groups" (Specific Examples Group G14) include the divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described in Specific Examples Group G3.

[0081] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0082] [ka]

[0083] [ka]

[0084] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.

[0085] [ka]

[0086] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. Equations Q9 and Q 10 These elements may be bonded to each other via single bonds to form a ring. In the general formulas (TEMP-53) to (TEMP-62) above, * represents a bond position.

[0087] [ka]

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

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

[0090] [ka]

[0091] [ka]

[0092] [ka]

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

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] [ka]

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

[0099] The above is a description of the substituents described herein.

[0100] • "When they combine to form a ring" In this specification, the phrase "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring, join together to form a substituted or unsubstituted fused ring, or do not join together" means the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring," the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted fused ring," and the case where "one or more pairs of adjacent elements do not join together." In this specification, the cases in which "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "cases where elements bond to form a ring") will be explained below. An example will be given of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.

[0101] [ka]

[0102] For example, R921 ~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.

[0103] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0104] [ka]

[0105] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above 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 R 922 Share.

[0106] [ka]

[0107] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, based solely on the structure of the formed ring. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can be saturated or unsaturated. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) is A , and ring Q C This is a "condensed ring". The ring Q of the general formula (TEMP-105) A and Q C This refers to the Q environment. A and Q C The ring Q of the general formula (TMEP-104) is formed by the condensation of the two rings. A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0108] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the mother skeleton or with a plurality of atoms of the mother skeleton and one or more arbitrary elements. For example, in the general formula (TEMP-104), the ring Q formed by the bonding of R 921 and R 922 means a ring formed by a carbon atom of the anthracene skeleton to which R A is bonded, a carbon atom of the anthracene skeleton to which R 921 is bonded, and one or more arbitrary elements. Specific examples include, when forming the ring Q 922 with R 921 and R 922 , when forming a monocyclic unsaturated ring with a carbon atom of the anthracene skeleton to which R A is bonded, a carbon atom of the anthracene skeleton to which R 921 is bonded, and four carbon atoms, the ring formed by R 922 and R 921 and R 922 is a benzene ring.

[0109] Here, "arbitrary element" is preferably at least one element selected from the group consisting of carbon element, nitrogen element, oxygen element, and sulfur element, unless otherwise specified in this specification. In an arbitrary element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. When an arbitrary element other than the carbon element is included, the formed ring is a heterocyclic ring. The "one or more arbitrary elements" constituting the monoring or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5, unless otherwise specified herein. Unless otherwise specified herein, the preferred form is a monoring or a fused ring. Unless otherwise specified herein, the "unsaturated ring" is preferred over the "saturated ring". Unless otherwise specified herein, “monocyclic” is preferably a benzene ring. Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.

[0110] When the above-mentioned "monocyclic ring" or "fused ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. The above explains the cases in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" ("the case of combining to form a ring").

[0111] • Substituents in the phrase "substituted or unsubstituted" In one embodiment described herein, the substituent referred to as "substituted or unsubstituted" (which may be referred to herein as "any substituent") is, for example, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming 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 ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R903 If there are two or more of them, then there are two or more R 903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.

[0112] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.

[0113] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, Ring-forming aryl groups with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.

[0114] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0115] Unless otherwise specified herein, adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, such as those described above.

[0116] In this specification, a numerical range expressed using "AA~BB" means a range that includes the numerical value AA, which is listed before "AA~BB", as the lower limit, and the numerical value BB, which is listed after "AA~BB", as the upper limit.

[0117] [First Embodiment] (compound) The compound according to this embodiment is a compound represented by the following general formula (1).

[0118] [ka]

[0119] (In the above general formula (1), A set consisting of R1 and R2, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R1 and R2, which do not form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted fused ring, are each independently: Substituted or unsubstituted alkyl groups with 1 to 4 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Ring A XThis is a ring represented by the general formula (1A-1) or (1A-2), The ring represented by the general formula (1A-1) above is condensed with ring Cx at position a, The ring represented by the general formula (1A-2) above is condensed with ring Cx at position b or c, Ring B X This is a ring represented by the general formula (1B-1), The ring represented by the general formula (1B-1) is condensed with ring Cx at positions d, e, f, or g. The ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1) each independently have one or more substituents represented by the following general formula (11) attached to them, or they do not have any substituents attached. At least one of the rings represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1) has one or more aryl groups Ar1 bonded to it. Ar1 is Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, A substituted or unsubstituted benzofluoranthenyl group, (It is a substituted or unsubstituted perilenyl group.)

[0120] [ka]

[0121] (In the above general formula (11), n 11 is 0, 1, 2, or 3, L 11 teeth, Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, Substituted or unsubstituted benzofluoranthenyl groups, and A divalent arylene group derived by removing one hydrogen atom from the aryl ring of either a substituted or unsubstituted perilen group, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, L 11 The heterocyclic group includes at least one atom selected from the group consisting of oxygen, sulfur, silicon, phosphorus, and boron as a heteroatom. When n11 is 0, L 11 This represents a single bond, Ar 11 teeth, Is it a hydrogen atom? Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, A substituted or unsubstituted benzofluoranthenyl group, Either a substituted or unsubstituted perilenyl group, These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Ar 11 The heterocyclic group includes at least one atom selected from the group consisting of oxygen, sulfur, silicon, phosphorus, and boron as a heteroatom. * indicates the bond location.

[0122] In the compound according to this embodiment, when the ring represented by general formula (1A-2) condenses with ring Cx at position b, the compound represented by general formula (1) is represented by the following general formula (1A-2a). Furthermore, when the ring represented by general formula (1A-2) condenses with ring Cx at position c, the compound represented by general formula (1) is represented by the following general formula (1A-2b).

[0123] [ka]

[0124] In the compound according to this embodiment, for example, when the ring represented by the general formula (1B-1) condenses with the ring Cx at position d, the compound represented by the general formula (1) is represented by the following general formula (1B-1a) or (1B-b). Also, for example, when the ring represented by the general formula (1B-1) condenses with the ring Cx at position e, the compound represented by the general formula (1) is represented by the following general formula (1B-1c) or (1B-1d).

[0125] [ka]

[0126] In the compound according to this embodiment, ring A XIt is preferable that the ring is represented by the general formula (1A-1) mentioned above.

[0127] The compound according to this embodiment (the compound represented by the general formula (1)) is preferably a compound represented by the following general formulas (1C), (1D), (1E), or (1F), and more preferably a compound represented by the following general formula (1C).

[0128] [ka]

[0129] In the above general formulas (1C), (1D), (1E), and (1F), R1 and R2 are, independently of each other, equivalent to R1 and R2 in the general formula (1) above. R3~R 18 Each of them operates independently. The aryl group Ar1, A substituent represented by the general formula (11), or It is a hydrogen atom, However, R3~R 18 At least one of them is the aryl group Ar1. Note: R3~R 18 When it is a hydrogen atom, it means that neither the aryl group Ar1 nor the substituent represented by the general formula (11) is substituted.

[0130] In the compound according to this embodiment, the aryl groups R1 and R2 are, Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, A substituted or unsubstituted benzofluoranthenyl group, It is preferable that the perilennyl group be substituted or unsubstituted.

[0131] In the compound according to this embodiment, the heterocyclic groups R1 and R2 are preferably substituted or unsubstituted heterocyclic groups having 5 to 30 ring-forming atoms, and more preferably substituted or unsubstituted heterocyclic groups having 5 to 18 ring-forming atoms.

[0132] In the compound according to this embodiment, R1 and R2 are preferably independently substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms.

[0133] In the compound according to this embodiment, R1 and R2 are preferably independently a methyl group or an ethyl group.

[0134] In the compound according to this embodiment, it is preferable that R1 and R2 do not bond to each other and do not form a ring.

[0135] In the compound according to this embodiment, the aryl group Ar1 is preferably a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted benzoanthryl group.

[0136] In the compound according to this embodiment, Ar 11 It is also preferable that one or more of the hydrogen atoms are deuterium atoms.

[0137] In the compound according to this embodiment, Ar 11 The aryl group is preferably a substituted or unsubstituted phenyl group.

[0138] In the compound according to this embodiment, L 11 The heterocyclic group preferably contains an oxygen atom or a silicon atom as a heteroatom.

[0139] In the compound according to this embodiment, L 11 The heterocyclic group is preferably a divalent heterocyclic group with 5 to 16 substituted or unsubstituted ring-forming atoms.

[0140] In the compound according to this embodiment, n11 is preferably 0. When n11 is 0, Ar 11 It is directly bonded by single bonds to the carbon atoms constituting the ring represented by general formula (1A-1), the ring represented by general formula (1A-2), and the ring represented by general formula (1B-1). In the compound according to this embodiment, n11 is also preferably 1.

[0141] In the compound according to this embodiment, it is preferable that the substituent represented by general formula (11) is not bonded to any of the rings represented by general formula (1A-1), general formula (1A-2), or general formula (1B-1).

[0142] The compound according to this embodiment is ring A X or Ring B X It is preferable that only one aryl group Ar1 is bonded to (that is, one of the rings represented by general formula (1A-1), the ring represented by general formula (1A-2), and the ring represented by general formula (1B-1).

[0143] In the compound according to this embodiment, one aryl group Ar1 is ring A X It is also preferable for them to bond.

[0144] In the compound according to this embodiment, it is also preferable that R4 in the general formulas (1C) and (1D) is an aryl group Ar1.

[0145] In the compound according to this embodiment, R of the general formula (1C) 13 It is also preferable that it be an aryl group Ar1.

[0146] In the compound according to this embodiment, it is also preferable that R9 in the general formula (1D) is an aryl group Ar1.

[0147] In the compound according to this embodiment, one aryl group Ar1 is ring B X It is also preferable for them to bond.

[0148] In the compounds according to this embodiment, it is also preferable that R4 in the general formulas (1E) and (1F) is an aryl group Ar1.

[0149] In the compound according to this embodiment, the aryl group Ar1 is Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, A substituted or unsubstituted pyrenyl group, It is also preferable that the triphenylenyl group be substituted or unsubstituted.

[0150] The compound according to this embodiment preferably does not contain heteroatoms.

[0151] In the compound according to this embodiment, the substituent ("any substituent") in the phrase "substituted or unsubstituted" is, for example, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -S-(R 905 A base represented by ) halogen atom, Nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is also preferable that the group is selected from the group consisting of the following: 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from one another. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from one another. R 903 If there are two or more of them, then there are two or more R 903 They are either identical or different from one another. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from one another. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from one another. R 906 If there are two or more of them, then there are two or more R906 They are either identical or different from one another. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.

[0152] In the compound according to this embodiment, the substituent referred to as "substituted or unsubstituted" is: Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is preferable that the group is selected from the group consisting of the following.

[0153] In the compound according to this embodiment, the substituent referred to as "substituted or unsubstituted" is: Unsubstituted alkyl groups with 1 to 18 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 18 ring-forming atoms It is more preferable that the group be selected from the group consisting of the following.

[0154] In the compounds according to this embodiment, the aryl group referred to as "substituted or unsubstituted aryl group" is: Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranteyl group, or It is preferable that it be a perilenyl group.

[0155] In the compound according to this embodiment, it is preferable that all of the groups described as "substituted or unsubstituted" are unsubstituted.

[0156] • Method for producing the compound according to this embodiment The compounds according to this embodiment can be produced according to the synthesis method described in the examples below. Alternatively, the compounds according to this embodiment can also be produced by following the synthesis method and using known alternative reactions and raw materials tailored to the target product.

[0157] • Specific examples of compounds according to this embodiment Specific examples of compounds according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples. In this specification, deuterium atoms are denoted as D in chemical formulas, and light hydrogen atoms are denoted as H or omitted from the description.

[0158] [ka]

[0159] [ka]

[0160]

change

[0161]

change

[0162]

change

[0163]

change

[0164]

change

[0165]

change

[0166]

change

[0167]

change

[0168]

change

[0169]

change

[0170]

change

[0171]

change

[0172]

change

[0173]

change

[0174]

change

[0175]

change

[0176]

change

[0177]

change

[0178]

change

[0179]

change

[0180]

change

[0181]

change

[0182]

change

[0183]

change

[0184]

change

[0185]

change

[0186]

change

[0187]

change

[0188]

change

[0189]

change

[0190]

change

[0191]

change

[0192]

change

[0193]

change

[0194]

change

[0195]

change

[0196]

change

[0197]

change

[0198]

change

[0199]

change

[0200]

change

[0201]

change

[0202] [ka]

[0203] [ka]

[0204] [ka]

[0205] [ka]

[0206] [ka]

[0207] [ka]

[0208] The compound according to this embodiment has a condensed fluorene structure in which a ring structure is condensed onto fluorene, and therefore exhibits excellent excitation resistance. The compound according to this embodiment has a structure in which a ring represented by the general formula (1B-1), consisting of four six-membered rings, is condensed onto ring Cx. Therefore, the compound according to this embodiment has improved excitation resistance compared to a compound having a structure in which an aryl ring (e.g., a phenanthrene ring) consisting of three six-membered rings is condensed onto ring Cx. By using the compound according to this embodiment in an organic EL device, an improvement in device lifespan can be expected. The compound according to this embodiment can be suitably used as a host material for the light-emitting layer of an organic EL device.

[0209] [Second Embodiment] (Materials for organic electroluminescent devices) The organic EL element material according to this embodiment contains the compound according to the first embodiment. One embodiment is an organic EL element material containing only the compound according to the first embodiment. Another embodiment is an organic EL element material containing the compound according to the first embodiment and another compound different from the compound in the first embodiment. In the organic EL element material of this embodiment, it is preferable that the compound according to the first embodiment is the host material. In this case, the organic EL element material may include the compound according to the first embodiment as the host material and other compounds such as dopant materials.

[0210] The compound according to the first embodiment is useful as a material for organic EL devices, useful as a material for the light-emitting layer of an organic EL device, and in particular useful as a host material for the blue light-emitting layer.

[0211] [Third Embodiment] (Organic electroluminescent element) The organic EL element according to this embodiment will be described below. The organic EL element according to this embodiment contains the compound according to the first embodiment as the first compound.

[0212] The organic EL element according to this embodiment includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating multiple layers composed of organic compounds. The organic layer may further contain an inorganic compound. In the organic EL element according to this embodiment, at least one layer of the organic layer contains the first compound (the compound according to the first embodiment).

[0213] In the organic EL element of this embodiment, it is preferable that at least one of the organic layers has a light-emitting region. In the organic EL element of this embodiment, it is preferable that the light-emitting region contains at least one light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by the general formula (1).

[0214] In the organic EL element according to this embodiment, the organic layer has an emissive region, the emissive region includes a first emissive layer and a second emissive layer, and it is also preferable that the first emissive layer contains a first compound as a first host material.

[0215] If the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL element according to this embodiment may have, for example, an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order. Alternatively, for example, the order of the first light-emitting layer and the second light-emitting layer may be reversed, and the element may have an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order.

[0216] When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, it is also preferable that the organic EL element according to this embodiment includes a second light-emitting layer between the anode and the cathode, and that the first light-emitting layer is disposed between the anode and the second light-emitting layer. When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, it is also preferable that the organic EL element according to this embodiment includes a first light-emitting layer between the anode and the cathode, and that a second light-emitting layer is disposed between the anode and the first light-emitting layer.

[0217] (Emission wavelength of organic EL elements) In this embodiment, the organic EL element preferably emits light with a maximum peak wavelength of 500 nm or less when the element is driven, and more preferably emits light with a peak wavelength of 430 nm or more and 480 nm or less. The maximum peak wavelength of light emitted by the organic EL element during element drive is measured as follows: Current density is 10 mA / cm². 2 The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage is applied to the element in such a manner. The peak wavelength of the emission spectrum with the maximum emission intensity is measured from the obtained spectral radiance spectrum and defined as the maximum peak wavelength (unit: nm).

[0218] The method for measuring the maximum peak wavelength of a compound in this specification is as follows: 10-6 mol / L or more 10 -5 Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. Measure the emission spectrum of this sample at room temperature (300K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the maximum emission peak wavelength. In this specification, the maximum peak wavelength may be referred to as the maximum fluorescence emission peak wavelength (FL-peak).

[0219] In the organic EL element according to this embodiment, the organic layer may consist only of an emissive layer, but the organic layer may further include at least one layer selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, and an electron barrier layer.

[0220] In the organic EL element according to this embodiment, it is preferable to have a hole transport layer between the anode and the light-emitting region. In the organic EL element according to this embodiment, if the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the first light-emitting layer and then to the second light-emitting layer, it is preferable to have a hole transport layer between the anode and the first light-emitting layer. Also, if the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side to the second light-emitting layer and then to the first light-emitting layer, it is preferable to have a hole transport layer between the anode and the second light-emitting layer.

[0221] In the organic EL element according to this embodiment, it is preferable to have an electron transport layer between the cathode and the light-emitting region. In the organic EL element according to this embodiment, if the light-emitting region includes a first light-emitting layer and a second light-emitting layer, and the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side in the order of the first light-emitting layer and the second light-emitting layer, it is preferable to have an electron transport layer between the cathode and the second light-emitting layer. Also, if the stacking order of the first light-emitting layer and the second light-emitting layer is from the anode side in the order of the second light-emitting layer and the first light-emitting layer, it is preferable to have an electron transport layer between the cathode and the first light-emitting layer.

[0222] Figure 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1A shown in Figure 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A includes, in order from the anode 3 side, a hole transport band 6, an emission region 5A, and an electron transport band 7. The hole transport band 6 includes, in order from the anode 3 side, a hole injection layer 61 and a hole transport layer 62. The emission region 5A includes one emission layer 5. The electron transport band 7 includes, in order from the emission region 5A side, an electron transport layer 71 and an electron injection layer 72.

[0223] (Emitting layer) The light-emitting layer 5 contains the compound according to the first embodiment. In the organic EL element 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the general formula (1A) or (1B).

[0224] (Luminescent compound) In the organic EL element 1A, the light-emitting layer 5 may further contain a light-emitting compound (preferably a fluorescent compound).

[0225] (Compound represented by general formula (5)) In one embodiment of the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by the following general formula (5).

[0226] [ka]

[0227] (In the above general formula (5), R 501 ~R 507 and R 511 ~R 517 Of these, one or more pairs consisting of two or more adjacent items, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 501 ~R 507 and R 511 ~R 517 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 521 and R 522 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0228] In luminescent compounds, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Preferably, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another.

[0229] "R 501 ~R 507 and R 511 ~R 517 "A set of two or more adjacent elements" is, for example, R 501 and R 502 A group consisting of R 502 and R 503 A group consisting of R 503 and R 504 A group consisting of R 505 and R 506 A group consisting of R 506 and R 507 A group consisting of R 501 and R 502 and R 503 This is a combination of sets and other elements.

[0230] In one embodiment, the compound represented by the general formula (5) is the compound represented by the following general formula (52).

[0231] [ka]

[0232] (In the above general formula (52), R531 ~R 534 and R 541 ~R 544 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 531 ~R 534 , R 541 ~R 544 , and R 551 and R 552 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 561 ~R 564 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0233] (Compounds represented by general formula (6)) In one embodiment of the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by the following general formula (6).

[0234] [ka]

[0235] (In the above general formula (6), Rings a, b, and c are each independent of the others. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. R 601 and R602 Each of these rings independently bonds with the a, b, or c ring to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R that does not form the aforementioned substituted or unsubstituted heteroalgebra 601 and R 602 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0236] In one embodiment of the organic EL element according to this embodiment, the a-ring, b-ring, and c-ring are rings that condense into the central condensed two-ring structure of the general formula (6) composed of a boron atom and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 ring-forming atoms).

[0237] The aromatic hydrocarbon rings of rings a, b, and c have the same structure as compounds in which a hydrogen atom has been introduced to an aryl group. The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central condensed biring structure of general formula (6) as ring-forming atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms on the central condensed two-ring structure of general formula (6) as ring-forming atoms.

[0238] Specific examples of "substituted or unsubstituted ring-forming aromatic hydrocarbon rings with 6 to 50 carbon atoms" include compounds in which a hydrogen atom has been introduced to the "aryl group" described in specific example group G1. The heterocyclic rings of the a, b, and c rings have the same structure as compounds in which a hydrogen atom is introduced into the heterocyclic group described above. The heterocycle of ring a includes three carbon atoms on the central fused biring structure of general formula (6) as ring-forming atoms. The heterocycles of rings b and c include two carbon atoms on the central fused biring structure of general formula (6) as ring-forming atoms. Specific examples of "heterocycles with 5 to 50 substituted or unsubstituted ring-forming atoms" include compounds in which hydrogen atoms are introduced into the "heterocycle group" described in specific example group G2.

[0239] R 601 and R 602 Each of these may independently bond with a ring a, a ring b, or a ring c to form a substituted or unsubstituted heterocycle. In this case, the heterocycle contains a nitrogen atom on the central fused biring structure of general formula (6). In this case, the heterocycle may also contain heteroatoms other than nitrogen. 601 and R 602 Specifically, when it is said that it bonds with ring a, ring b, or ring c, it means that it bonds with an atom constituting ring a, ring b, or ring c and R 601 and R 602 This means that the atoms that make up the compound are bonded together. For example, R 601 It binds to the a ring, R 601 A nitrogen-containing heterocycle of two-ring condensation (or three-ring condensation or more) may be formed by the condensation of a ring containing a nitrogen ring with an a-ring. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to two-ring condensation or more heterocyclic groups containing nitrogen. R 601 When it bonds with the b ring, R 602 When it bonds with the a ring, and R 602 The same applies when it is bonded to a c-ring. R 601 and R 602 Each of these elements does not necessarily have to be bonded to an a-ring, b-ring, or c-ring independently.

[0240] In one embodiment, the a-ring, b-ring, and c-ring in the general formula (6) are each independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring-forming carbon atoms. In one embodiment, the a-ring, b-ring, and c-ring in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0241] In one embodiment, R in the general formula (6) 601 and R 602 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Preferably, it is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms that forms a ring.

[0242] In one embodiment, the compound represented by the general formula (6) is the compound represented by the following general formula (62).

[0243] [ka]

[0244] (In the above general formula (62), R 601A R 611 and R 621 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 602A R 613 and R 614 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R that does not form the aforementioned substituted or unsubstituted heteroalgebra 601A and R 602A Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 611 ~R 621 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted heterocycle, does not form the aforementioned substituted or unsubstituted monocycle, and does not form the aforementioned substituted or unsubstituted fused ring. 611 ~R 621 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted. (In the above general formula (62), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different to one another.

[0245] R in the above general formula (62) 601A and R 602A These are, respectively, R in the general formula (6) above. 601 and R 602 It is the corresponding base. For example, R 601A and R 611 These may bond to form a two-ring condensation (or three-ring condensation or more) nitrogen-containing heterocycle in which the ring containing these and the benzene ring corresponding to the a-ring are fused. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to two-ring condensation or more heterocycle groups containing nitrogen. 601A and R 621 When they are joined, R602A and R 613 When they are joined, and R 602A and R 614 The same applies when they are joined together.

[0246] R 611 ~R 621 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a substituted or unsubstituted monoring, or They may bond to each other to form substituted or unsubstituted fused rings. For example, R 611 and R 612 These rings may bond together to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring, or benzothiophene ring is fused to the six-membered ring to which they are bonded. The resulting fused ring may be a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring.

[0247] In one embodiment, the compound represented by the general formula (6) is the compound represented by the following general formula (42-2).

[0248] [ka]

[0249] (In the above general formula (42-2), R 611 ~R 617 , R 601A and R 602A Each of these independently corresponds to R in the general formula (62) above. 611 ~R 617 , R 601A and R 602A It is synonymous with, X4 is an oxygen atom or a sulfur atom. R 701 ~R 704 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 701 ~R 704 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. In the above general formula (42-2), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of these independently corresponds to R in the general formula (62) above. 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 (This is synonymous with...)

[0250] (Compounds represented by general formula (3A)) In one embodiment of the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is a compound represented by the following general formula (3A).

[0251] [ka]

[0252] (In the above general formula (3A), Ra 301 Ra 302 Ra 303 Ra 304 Ra 305 Ra 306 Ra 307 Ra 308 Ra 309 and Ra 310 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, Ra 301 ~Ra 310 At least one of them is a monovalent group represented by the following general formula (31A), Ra that does not form the aforementioned monocyclic ring, does not form the aforementioned fused ring, and is not a monovalent group represented by the following general formula (31A) 301 ~Ra 310 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0253] [ka]

[0254] (In the above general formula (31A), Ara 301 and Ara 302 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. La 301 , La 302 and La 303 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, * indicates the bond position in the pyrene ring in the general formula (3A).

[0255] (Specific examples of luminescent compounds) The following are examples of luminescent compounds, but these are merely illustrative examples, and luminescent compounds are not limited to these examples.

[0256] [ka]

[0257] [ka]

[0258]

change

[0259]

change

[0260]

change

[0261]

change

[0262]

change

[0263]

change

[0264]

change

[0265]

change

[0266]

change

[0267] In the organic EL element 1A, the luminescent compound contained in the light-emitting layer 5 is preferably a compound that exhibits light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits light emission between 430 nm and 480 nm. In the organic EL element 1A, the luminescent compound contained in the light-emitting layer 5 is preferably a compound that exhibits fluorescent emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescent emission between 430 nm and 480 nm.

[0268] In the organic EL element 1A, when the light-emitting layer 5 includes a compound according to the first embodiment and a light-emitting compound, the compound according to the first embodiment (first compound) is preferably a host material (sometimes referred to as a matrix material), and the light-emitting compound is preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material).

[0269] In this specification, "host material" refers to, for example, a material that makes up "50% by mass or more of the layer." Therefore, for example, in the case of organic EL element 1A, the light-emitting layer 5 contains the compound represented by the general formula (1A) in an amount of 50% by mass or more of the total mass of the light-emitting layer.

[0270] (film thickness of the light-emitting layer) The film thickness of the light-emitting layer 5 is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the film thickness of the light-emitting layer is 5 nm or more, it is easier to form the light-emitting layer and easier to adjust the chromaticity. When the film thickness of the light-emitting layer is 50 nm or less, it is easier to suppress the rise in the driving voltage.

[0271] (Compound content in the luminescent layer) When the light-emitting layer 5 contains the compound according to the first embodiment and the luminescent compound, the content of the compound according to the first embodiment and the luminescent compound in the light-emitting layer 5 is preferably, for example, within the following ranges. The compound content according to the first embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the luminescent compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the compound according to the first embodiment and the luminescent compound in the light-emitting layer 5 is 100% by mass.

[0272] This embodiment does not exclude the possibility that the light-emitting layer 5 may contain materials other than the compound and light-emitting compound according to the first embodiment. The light-emitting layer 5 may contain only one compound according to the first embodiment, or it may contain two or more compounds.

[0273] Figure 2 shows a schematic configuration of another example of an organic EL element according to this embodiment. The organic EL element 1B shown in Figure 2 differs from the organic EL element 1A in that the organic layer 10B includes a first light-emitting region 5B, but is otherwise the same as the organic EL element 1A. The first light-emitting region 5B includes a first light-emitting layer 51 and a second light-emitting layer 52, in that order from the anode 3 side. The first light-emitting layer 51 contains the first compound, and the second light-emitting layer 52 contains the second compound.

[0274] (First compound) In the organic EL element 1B, the first compound is the compound according to the first embodiment. In the organic EL element according to this embodiment, the first compound is preferably a compound represented by the general formula (1).

[0275] (Second compound) In the organic EL element 1B, the second compound is not particularly limited, but examples include the second compound represented by the following general formula (2). In one embodiment of the organic EL element 1B, the second compound is a compound represented by the following general formula (2).

[0276] [ka]

[0277] (In the above general formula (2), R 201 ~R 208 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 801 A base represented by -COOR 802 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 201 and L 202 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar 201 and Ar 202 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0278] (In the second compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 801 and R 802 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.

[0279] In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group represented by the following general formula (HY1) in its molecule.

[0280] [ka]

[0281] (In the above general formula (HY1), R Y1 ~R Y8 and R Y11 ~R Y14 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Nitro group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. ny is either 0 or 1. however, When ny is 0, R Y1 ~R Y8 One of the selected options is a single bond that connects to *e, When ny is 1, R Y1 and R Y2 , R Y2 and R Y3 or R Y3 and R Y5 One of them is a single bond that connects to *cy, R Y1 and R Y2 , R Y2 and R Y3 or R Y3 and R Y5 The other side is a single bond that connects to *dy, R Y5 ~R Y8 , R Y11 ~R Y14 , as well as R which is not a single bond attached to *cy and *dy Y1 ~R Y4 One of the selected options is a single bond that connects to *e, Z2 is either an oxygen atom or a sulfur atom. *fy indicates the bonding position with the atom in the second compound.

[0282] In one embodiment of the organic EL element 1B, when ny in the general formula (HY1) is 0, the group represented by the general formula (HY1) is represented by the following general formula (HY10). In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group represented by the following general formula (HY10) in its molecule.

[0283] [ka]

[0284] (In the above general formula (HY10), R Y1 ~RY8 , and Z2 are, respectively, R in the general formula (HY1). Y1 ~R Y8 , and is synonymous with Z2, However, R Y1 ~R Y8 One of the selected options is a single bond that joins *ey, *fy indicates the bonding position with the atom in the second compound.

[0285] In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group represented by the general formula (HY1) in its molecule, and ny is 1.

[0286] In one embodiment of the organic EL element 1B, the second compound is a compound having at least one group selected from the group consisting of groups represented by the following general formulas (HY11), (HY12), and (HY13) in its molecule.

[0287] [ka]

[0288] (In the above general formulas (HY11), (HY12), and (HY13), R Y1 ~R Y8 , R Y11 ~R Y14 , and Z2 are, respectively, R in the general formula (HY1). Y1 ~R Y8 , R Y11 ~R Y14 , and is synonymous with Z2, However, R Y1 ~R Y8 and R Y11 ~R Y14 Of these, one is a single bond that connects to *ey, *fy indicates the bonding position with the atom in the second compound.

[0289] In one embodiment of the organic EL element 1B, the second compound is a compound represented by the general formula (2), and the molecule of the compound represented by the general formula (2) contains at least one group represented by the general formula (HY1).

[0290] In one embodiment of the organic EL element 1B, Ar in the general formula (2) 201 and Ar 202 At least one of them is a group represented by the general formula (HY1).

[0291] In one embodiment of the organic EL element 1B, Ar in the general formula (2) 201 Or Ar 202 However, this is the group represented by the general formula (HY1) mentioned above.

[0292] In one embodiment of the organic EL element 1B, the second compound is a compound represented by the general formula (2), and the molecule of the compound represented by the general formula (2) contains at least one group selected from the group consisting of groups represented by the general formulas (HY11), (HY12), and (HY13).

[0293] In one embodiment of the organic EL element 1B, Ar in the general formula (2) 201 and Ar 202 At least one of them is a group selected from the group consisting of groups represented by the general formulas (HY11), (HY12), and (HY13).

[0294] In one embodiment of the organic EL element 1B, Ar in the general formula (2) 201 Or Ar 202 However, it is one of the groups selected from the group consisting of the groups represented by the general formulas (HY11), (HY12), and (HY13).

[0295] In one embodiment of the organic EL element 1B, the excitation resistance of the second compound is improved by having at least one group selected from the group consisting of groups represented by the general formulas (HY1), (HY10), (HY11), (HY12), and (HY13) in its molecule. By using such a second compound in the second light-emitting layer, the lifespan of the organic EL element is easily extended.

[0296] In one embodiment of the organic EL element 1B, the groups described as "substituted or unsubstituted" in the second compound are all "unsubstituted" groups.

[0297] (Method for producing the second compound) The second compound according to this embodiment can be produced by known methods, or by following those methods and using known alternative reactions and raw materials suited to the target product.

[0298] (Specific examples of the second compound) Specific examples of the second compound according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.

[0299] [ka]

[0300] [ka]

[0301] [ka]

[0302] [ka]

[0303] [ka]

[0304]

change

[0305]

change

[0306]

change

[0307]

change

[0308]

change

[0309]

change

[0310]

change

[0311]

change

[0312]

change

[0313]

change

[0314]

change

[0315]

change

[0316]

change

[0317]

change

[0318]

change

[0319]

change

[0320]

change

[0321]

change

[0322]

change

[0323]

change

[0324]

change

[0325]

change

[0326]

change

[0327]

change

[0328]

change

[0329]

change

[0330]

change

[0331]

change

[0332]

change

[0333]

change

[0334]

change

[0335]

change

[0336]

change

[0337]

change

[0338]

change

[0339]

change

[0340]

change

[0341]

change

[0342]

change

[0343]

change

[0344]

change

[0345]

change

[0346] [ka]

[0347] [ka]

[0348] [ka]

[0349] [ka]

[0350] [ka]

[0351] [ka]

[0352] [ka]

[0353] [ka]

[0354] In the following specific examples of compounds, D represents a deuterium atom, z, z1, z2, z3, z4, z5, and z6 each represent the number of deuterium atoms bonded to the ring, z is an integer between 1 and 8, z1 is an integer between 1 and 9, z2 to z5 are integers between 1 and 5, and z6 is an integer between 1 and 7.

[0355] [ka]

[0356] [ka]

[0357] [ka]

[0358] [ka]

[0359] [ka]

[0360] [ka]

[0361] [ka]

[0362] [ka]

[0363] (First luminescent compound and second luminescent compound) In the organic EL element 1B, the first light-emitting layer 51 may also preferably contain a first light-emitting compound. The first light-emitting compound is preferably a fluorescent compound. In the organic EL element 1B, the second light-emitting layer 52 may also preferably contain a second light-emitting compound. The second light-emitting compound is preferably a fluorescent compound. When the first light-emitting layer 51 contains a first light-emitting compound and the second light-emitting layer 52 contains a second light-emitting compound, the first light-emitting compound and the second light-emitting compound are either identical or different from each other. Examples of the first and second luminescent compounds are the same as those exemplified in the organic EL element 1A.

[0364] In the organic EL element 1B, the first luminescent compound contained in the first light-emitting layer 51 is preferably a compound that exhibits light emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits light emission between 430 nm and 480 nm. In the organic EL element 1B, the first luminescent compound contained in the first light-emitting layer 51 is preferably a compound that exhibits fluorescence emission with a maximum peak wavelength of 500 nm or less, and more preferably a compound that exhibits fluorescence emission between 430 nm and 480 nm.

[0365] In the organic EL element 1B, if the first light-emitting layer 51 contains a first compound and a first luminescent compound, the first compound is preferably a first host material, and the first luminescent compound is preferably a first dopant material. Furthermore, in the organic EL element 1B, if the second light-emitting layer 52 contains a second compound and a second luminescent compound, the second compound is preferably a second host material, and the second luminescent compound is preferably a second dopant material.

[0366] The second light-emitting layer contains a second host material, The triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the following relationship (Equation 1): The organic electroluminescent element according to claim 14 or claim 15. T1(H1)>T1(H2) …(Math 1) In the organic EL element 1B, the second light-emitting layer 52 preferably contains a second host material, and the triplet energy T1(H1) of the first host material and the triplet energy T1(H2) of the second host material satisfy the relationship shown in the following formula (Equation 1). T1(H1)>T1(H2) …(Math 1)

[0367] Conventionally, Triplet-Triplet-Annihilation (sometimes referred to as TTA) is known as a technique for improving the luminescence efficiency of organic EL devices. TTA is a mechanism in which triplet excitons collide with other triplet excitons to produce singlet excitons. The TTA mechanism is also sometimes referred to as the TTF mechanism, as described in International Publication No. 2010 / 134350.

[0368] This explains the TTF phenomenon. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As previously known, their spin states are 25% singlet excitons and 75% triplet excitons. In conventionally known fluorescent devices, 25% of singlet excitons emit light when they relax to the ground state, while the remaining 75% of triplet excitons return to the ground state through a thermal deactivation process without emitting light. Therefore, the theoretical limit of the internal quantum efficiency of conventional fluorescent devices was said to be 25%. Meanwhile, the behavior of triplet excitons generated within organic matter has been theoretically investigated. According to SMBachilo et al. (J.Phys.Chem.A,104,7711(2000)), assuming that higher-order excitons such as quintets quickly revert to triplets, triplet excitons (hereinafter, 3 A * When the density of (described as) increases, triplet excitons collide with each other, and the reaction shown in the following equation occurs. Here, 1 A represents the ground state, 1 A * This represents the lowest excited singlet exciton. 3 A * + 3 A * →(4 / 9) 1 A+(1 / 9) 1 A * +(13 / 9) 3 A * That is, 5 3 A * →4 1 A+1A *Therefore, it is predicted that 1 / 5, or 20%, of the 75% of triplet excitons initially generated will be converted into singlet excitons. Consequently, the singlet excitons contributing as light will be 40%, which is the initial 25% plus 75% × (1 / 5) = 15%. In this case, the ratio of emission from TTF to the total emission intensity (TTF ratio) will be 15 / 40, or 37.5%. Furthermore, if we assume that the 75% of the initially generated triplet excitons collide with each other to generate singlet excitons (one singlet exciton is generated from two triplet excitons), then a very high internal quantum efficiency of 62.5% is obtained, which is the initial 25% of singlet excitons plus 75% × (1 / 2) = 37.5%. In this case, the TTF ratio is 37.5 / 62.5 = 60%.

[0369] According to the organic EL element of this embodiment, triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer are less likely to be quenched even if there is an excess of carriers at the interface between the first light-emitting layer and the organic layer in direct contact with the first light-emitting layer. For example, if the recombination region is locally located at the interface between the first light-emitting layer and the hole transport layer or electron barrier layer, quenching by excess electrons is possible. On the other hand, if the recombination region is locally located at the interface between the first light-emitting layer and the electron transport layer or hole barrier layer, quenching by excess holes is possible. The organic EL element 1B comprises at least two light-emitting layers (i.e., a first light-emitting layer 51 and a second light-emitting layer 52) that satisfy a predetermined relationship. By arranging the first light-emitting layer 51 and the second light-emitting layer 52 such that the triplet energy T1(H1) of the first compound in the first light-emitting layer 51 and the triplet energy T1(H2) of the second compound in the second light-emitting layer 52 satisfy the relationship in the above formula (Equation 1), triplet excitons generated in the first light-emitting layer 51 can move to the second light-emitting layer 52 without being quenched by excess carriers, and the reverse movement from the second light-emitting layer 52 to the first light-emitting layer 51 can be suppressed. As a result, the TTF mechanism is activated in the second light-emitting layer 52, singlet excitons are efficiently generated, and the luminescence efficiency is improved. Thus, the organic EL element 1B comprises a first light-emitting layer 51 that mainly generates triplet excitons and a second light-emitting layer 52 that mainly exhibits the TTF mechanism by utilizing triplet excitons that have moved from the first light-emitting layer 51, as separate regions. By using a compound with a lower triplet energy than the first compound in the first light-emitting layer as the second compound in the second light-emitting layer 52, a difference in triplet energy is created, thereby improving the luminescence efficiency.

[0370] (Triplet energy T1) The following methods can be used to measure the triplet energy T1. The compound to be measured is placed in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) and 10 -5 mol / L or more 10 -4 Prepare a solution by dissolving the substance to a concentration of mol / L or less, and place this solution in a quartz cell to use as the measurement sample. Measure the phosphorescence spectrum of this sample at a low temperature (77[K]) (vertical axis: phosphorescence intensity, horizontal axis: wavelength). Draw a tangent line to the rise of the short-wavelength side of the phosphorescence spectrum, and measure the wavelength λ at the intersection of this tangent line and the horizontal axis. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is defined as the triplet energy T1. Conversion formula (F1): T1[eV]=1239.85 / λ edge

[0371] The tangent to the rise of the phosphorescence spectrum on the short-wavelength side is drawn as follows: When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum (i.e., the tangent at the inflection point) is considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurement, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer can be used. However, the measuring apparatus is not limited to this; measurements may also be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light-receiving device.

[0372] In the organic EL element 1B, when the first light-emitting layer 51 contains a first compound and a first luminescent compound, it is preferable that the singlet energy S1(H1) of the first compound and the singlet energy S1(D3) of the first luminescent compound satisfy the relationship shown in the following formula (Equation 2). S1(H1)>S1(D3)...(Math 2)

[0373] (Singlet energy S1) The following methods can be used to measure the singlet energy S1 using a solution (sometimes referred to as the solution method). 10 compounds to be measured -5 mol / L or more 10 -4 Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. Measure the absorption spectrum of this sample at room temperature (300K) (vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent line to the falling edge on the longer wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula (F2) to calculate the singlet energy S1. Conversion formula (F2): S1[eV]=1239.85 / λedge Examples of absorption spectrum measuring devices include, but are not limited to, Hitachi's spectrophotometer (device name: U3310).

[0374] The tangent to the falling edge of an absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangents at each point on the spectral curve as we move along the spectral curve in the longer wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the value of the slope is minimized on the longest wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the falling edge of the absorption spectrum on the longer wavelength side. Note that maximum absorbance values ​​of 0.2 or less are not included in the maximum value at the longest wavelength mentioned above.

[0375] In the organic EL element 1B, if the second light-emitting layer 52 contains a second compound and a second luminescent compound, the second compound is preferably a host material, and the second luminescent compound is preferably a dopant material.

[0376] In the organic EL element 1B, when the second light-emitting layer 52 contains a second compound and a second luminescent compound, it is preferable that the singlet energy S1(H2) of the second compound and the singlet energy S1(D4) of the second luminescent compound satisfy the relationship shown in the following formula (Equation 3). S1(H2)>S1(D4)...(Math 3)

[0377] The first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain phosphorescent material (dopant material). Furthermore, it is preferable that the first light-emitting layer 51 and the second light-emitting layer 52 do not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes. Furthermore, it is preferable that the first light-emitting layer 51 and the second light-emitting layer 52 do not contain metal complexes.

[0378] (film thickness of the light-emitting layer) The film thicknesses of the first light-emitting layer 51 and the second light-emitting layer 52 in the organic EL element 1B are preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. When the film thickness of the light-emitting layer is 5 nm or more, it is easier to form the light-emitting layer and adjust the chromaticity. When the film thickness of the light-emitting layer is 50 nm or less, it is easier to suppress the rise in the driving voltage.

[0379] (Compound content in the luminescent layer) When the first light-emitting layer 51 contains the first compound and the first luminescent compound, the content of the first compound and the first luminescent compound in the first light-emitting layer 51 is preferably, for example, within the following ranges. The content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the first luminescent compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the first compound and the first luminescent compound in the first light-emitting layer 51 is 100% by mass.

[0380] This embodiment does not exclude the possibility that the first light-emitting layer 51 may contain materials other than the first compound and the first light-emitting compound. The first light-emitting layer 51 may contain only one type of the first compound, or it may contain two or more types.

[0381] When the second light-emitting layer 52 contains the second compound and the second luminescent compound, the content of the second compound and the second luminescent compound in the second light-emitting layer 52 is preferably, for example, within the following ranges. The content of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less. The content of the second luminescent compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less. However, the upper limit of the total content of the second compound and the second luminescent compound in the second light-emitting layer 52 is 100% by mass.

[0382] This embodiment does not exclude the possibility that the second light-emitting layer 52 may contain materials other than the second compound and the second light-emitting compound. The second light-emitting layer 52 may contain only one type of the second compound, or it may contain two or more types.

[0383] In the organic EL element 1B, it is also preferable that the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact.

[0384] In the organic EL element 1B, when "the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact," the layer structure in which "the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact" may include, for example, any of the following embodiments (LS1), (LS2), and (LS3). (LS1) A configuration in which, during the process of depositing the compound relating to the first light-emitting layer 51 and the process of depositing the compound relating to the second light-emitting layer 52, a region is created in which both the first compound as a host material (hereinafter sometimes referred to as the "first host material") and the second compound as a host material (hereinafter sometimes referred to as the "second host material") are mixed, and this region is located at the interface between the first light-emitting layer 51 and the second light-emitting layer 52. (LS2) In a configuration in which the first light-emitting layer 51 and the second light-emitting layer 52 contain a light-emitting compound, a region in which the first host material, the second host material, and the light-emitting compound are mixed is generated during the process of vapor deposition of the compound related to the first light-emitting layer 51 and the vapor deposition of the compound related to the second light-emitting layer 52, and this region is located at the interface between the first light-emitting layer 51 and the second light-emitting layer 52. (LS3) A configuration in which, when the first light-emitting layer 51 and the second light-emitting layer 52 contain a light-emitting compound, a region made of the light-emitting compound, a region made of the first host material, or a region made of the second host material is generated during the process of vapor deposition of the compound relating to the first light-emitting layer 51 and the compound relating to the second light-emitting layer 52, and such region is located at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

[0385] When the organic EL element 1B includes a third light-emitting layer, it is preferable that the first light-emitting layer 51 and the second light-emitting layer 52 are in direct contact, and that the second light-emitting layer 52 and the third light-emitting layer are in direct contact.

[0386] In the organic EL element 1B, when "the second light-emitting layer 52 and the third light-emitting layer are in direct contact," the layer structure in which "the second light-emitting layer 52 and the third light-emitting layer are in direct contact" is: For example, any of the following embodiments (LS4), (LS5), and (LS6) may also be included. (LS4) A configuration in which, during the process of depositing the compound relating to the second light-emitting layer 52 and the process of depositing the compound relating to the third light-emitting layer, a region is created in which both the second host material and the third host material (the host material contained in the third light-emitting layer) are mixed, and this region is located at the interface between the second light-emitting layer 52 and the third light-emitting layer. (LS5) In a configuration in which the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region in which the second host material, the third host material, and the light-emitting compound are mixed is generated during the process of vapor deposition of the compound relating to the second light-emitting layer 52 and the vapor deposition of the compound relating to the third light-emitting layer, and this region is located at the interface between the second light-emitting layer 52 and the third light-emitting layer. (LS6) A configuration in which, when the second light-emitting layer 52 and the third light-emitting layer contain a light-emitting compound, a region made of the light-emitting compound, a region made of the second host material, or a region made of the third host material is generated during the process of vapor deposition of the compound relating to the second light-emitting layer 52 and the vapor deposition of the compound relating to the third light-emitting layer, and such region is located at the interface between the second light-emitting layer 52 and the third light-emitting layer.

[0387] The organic EL element 1B may also preferably have an intervening layer. If the organic EL element 1B has an intervening layer, it is preferable that the intervening layer is placed between the first light-emitting layer 51 and the second light-emitting layer 52.

[0388] (intervening layer) The intervening layer is preferably an undoped layer. The intervening layer is preferably free of metal atoms. The intervening layer includes an intervening layer material. Preferably, the intervening layer material is not a luminescent compound. The intervening layer material is not particularly limited, but it is preferable that it be a material other than a luminescent compound. Examples of intercalated layer materials include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; 2) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; and 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0389] The intervening layer material may be one or both of the first compound contained in the first light-emitting layer 51 and the second compound contained in the second light-emitting layer 52.

[0390] When the interlayer contains multiple interlayer materials, it is preferable that the content of each interlayer material is 10% by mass or more of the total mass of the interlayer. The intervening layer preferably contains the intervening layer material in an amount of 60% by mass or more of the total mass of the intervening layer, more preferably 70% by mass or more of the total mass of the intervening layer, even more preferably 80% by mass or more of the total mass of the intervening layer, even more preferably 90% by mass or more of the total mass of the intervening layer, and still more preferably 95% by mass or more of the total mass of the intervening layer. The intervening layer may contain only one type of intervening layer material, or it may contain two or more types. If the intervening layer contains two or more intervening layer materials, the upper limit of the total content of the two or more intervening layer materials is 100% by mass. This embodiment does not exclude the possibility that the intervening layer may contain materials other than the intervening layer material.

[0391] The intervening layer may consist of a single layer or of two or more layers stacked together.

[0392] There are no particular restrictions on the thickness of the intervening layer, but it is preferably 3 nm to 15 nm per layer, and more preferably 5 nm to 10 nm.

[0393] The configuration of each layer common to organic EL element 1A and organic EL element 1B will be further explained. Reference numerals may be omitted below.

[0394] (substrate) Substrate 2 is used as a support for the organic EL element. Substrate 2 can be made of, for example, glass, quartz, or plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), such as a plastic substrate. Materials for forming the plastic substrate include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic vapor-deposited film can also be used.

[0395] (anode) For the anode 3 formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). 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, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).

[0396] These materials are typically deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% by mass of zinc oxide relative to indium oxide. Similarly, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% by mass of tungsten oxide and 0.1% to 1% by mass of zinc oxide relative to indium oxide. Other methods such as vacuum deposition, coating, inkjet, and spin coating may also be used.

[0397] Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the anode's work function. Therefore, any material suitable for electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0398] Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.

[0399] (cathode) For the cathode 4, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0400] Furthermore, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Additionally, when using silver paste or similar materials, coating or inkjet methods can be employed.

[0401] Furthermore, by providing an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, or spin coating.

[0402] (Hole injection layer) The hole injection layer 61 is a layer containing a material with high hole injection properties. Examples of materials with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0403] Furthermore, substances with high hole injection potential include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino] Aromatic amine compounds such as [phenylaminobenzene] (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) are also examples, as is dipyradino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile (HAT-CN).

[0404] Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples of polymer compounds include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). In addition, polymer compounds to which acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) have been added can also be used.

[0405] (Hole transport layer) The hole transport layer 62 is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer 62. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl Aromatic amine compounds such as phenyl (abbreviated as DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. The substances described here are mainly 10 -6 cm 2 It is a substance having a hole mobility of / (V·s) or greater.

[0406] The hole transport layer 62 may use carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. High molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[0407] However, other materials may be used as long as they have higher hole transport capabilities than electron transport capabilities. Furthermore, the layer containing the material with high hole transport capabilities may be a single layer, or it may consist of two or more layers of the above-mentioned material stacked together.

[0408] (Specific examples of hole transport zone materials) Specific examples of hole transport band materials include the following compounds. However, the present invention is not limited to these specific examples of hole transport band materials.

[0409] [ka]

[0410] (electron transport layer) The electron transport layer 71 is a layer containing a material with high electron transport properties. The electron transport layer 71 can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, there are also 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be suitably used. The substances described herein are mainly 10 -6 cm 2 The material has an electron mobility of 1 / (V·s) or greater. However, any material with higher electron transport properties than hole transport properties may be used as the electron transport layer. Furthermore, the electron transport layer may consist of a single layer, or it may consist of two or more layers of the above material stacked together.

[0411] Furthermore, polymer compounds can also be used in the electron transport layer 71. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[0412] (Specific examples of electron transport materials) Specific examples of electron transport materials that can be used in electron transport layers include the following compounds. However, the present invention is not limited to these specific examples of electron transport materials.

[0413] [ka]

[0414] [ka]

[0415] (electron injection layer) The electron injection layer 72 is a layer containing a material with high electron injection properties. The electron injection layer 72 can contain alkali metals, alkaline earth metals, or compounds thereof, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). Alternatively, a material containing an alkali metal, alkaline earth metal, or a compound thereof in an electron-transporting material, specifically one containing magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently.

[0416] Alternatively, a composite material obtained by mixing an organic compound and an electron donor may be used in the electron injection layer 72. Such a composite material exhibits excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons, and specifically, for example, the substances that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0417] (Layer formation method) The method for forming each layer of the organic EL element in this embodiment is not limited to those specifically mentioned above, but known methods such as dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet deposition can be employed.

[0418] (film thickness) The film thickness of each organic layer in the organic EL element of this embodiment is not limited unless otherwise specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer in the organic EL element is usually preferably in the range of a few nanometers to 1 μm.

[0419] According to this embodiment, an organic electroluminescent element with improved lifespan can be provided.

[0420] [Fourth Embodiment] (electronic equipment) The electronic device according to this embodiment is equipped with an organic electroluminescent element according to the third embodiment. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lights. The light-emitting device can also be used in a display device, for example, as a backlight for a display device.

[0421] [Variations of the Embodiment] Furthermore, the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention.

[0422] For example, the number of light-emitting layers in an organic EL element is not limited to one or two layers; three or more light-emitting layers may be stacked. If an organic EL element has two or more light-emitting layers, it is sufficient that at least two of the light-emitting layers (the first light-emitting layer and the second light-emitting layer) satisfy the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers, or phosphorescent light-emitting layers that utilize light emission due to electron transitions from a triplet excited state to a direct ground state.

[0423] Furthermore, if the organic EL element has multiple light-emitting layers, these light-emitting layers may be arranged adjacent to each other, or it may be a so-called tandem type organic EL element in which multiple light-emitting units are stacked with an intermediate layer in between.

[0424] Furthermore, the specific structure and shape in the implementation of the present invention may be other structures, etc., to the extent that the objectives of the present invention can be achieved. [Examples]

[0425] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.

[0426] <Compound> The structure of the compound represented by general formula (1) used in the manufacture of the organic EL element according to the example, and the structure of the compound represented by general formula (1) according to the synthesis example are shown below.

[0427] [ka]

[0428] [ka]

[0429] The structure of the comparative compound used in the manufacture of the organic EL element in the comparative example is shown below.

[0430] [ka]

[0431] The structures of other compounds used in the organic EL elements in the examples and comparative examples are shown below.

[0432] [ka]

[0433] <Fabrication of Organic EL Devices (1)> Organic EL elements were fabricated and evaluated as follows.

[0434] [Example 1] A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25mm x 75mm x 1.1mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was set to 130 nm. After cleaning, the glass substrate with transparent electrode lines was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HA-1 was deposited on the side where the transparent electrode lines were formed, covering the transparent electrodes, to form a hole injection layer (HI) with a thickness of 5 nm. Following the deposition of the hole injection layer, compound HT-1 was deposited to form a first hole transport layer with a thickness of 80 nm. Following the deposition of the first hole transport layer, compound HT-2 was deposited to create a second hole transport layer (also called an electron barrier layer) with a thickness of 10 nm. Compound BH1-1, as the first compound, and compound BD-1, as the first luminescent compound, were co-deposited onto the second hole transport layer such that the proportion of compound BD-1 was 2% by mass, thereby forming a first luminescent layer with a thickness of 5 nm. Compound BH-2, as the second compound, and compound BD-1, as the second luminescent compound, were co-deposited onto the first luminescent layer such that the proportion of compound BD-1 was 2% by mass, thereby forming a second luminescent layer with a thickness of 20 nm. Compound ET-1 was deposited on the second light-emitting layer to form a first electron transport layer (also called a hole barrier layer) with a thickness of 10 nm. Compound ET-2 was deposited on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm. LiF was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. A cathode with a thickness of 80 nm was formed by depositing metallic aluminum onto the electron injection layer.

[0435] The element configuration of Example 1 is schematically shown below. ITO(130) / HA-1(5) / HT-1(80) / HT-2(10) / BH1-1:BD-1(5,98%:2%) / BH-2:BD-1(20,98%:2%) / ET-1(10) / ET-2(15) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Similarly, the percentage figures in parentheses (98%:2%) indicate the proportion (by mass) of compound BH1-1 or compound BH-2 and compound BD-1 in the first or second light-emitting layer.

[0436] [Comparative Example 1] The organic EL element of Comparative Example 1 was fabricated in the same manner as in Example 1, except that the first compound of the first light-emitting layer was changed to one of the compounds listed in Table 1.

[0437] <Evaluation of Organic EL Elements (1)> The organic EL elements fabricated in Example 1 and Comparative Example 1 were evaluated as follows. The evaluation results are shown in Table 1.

[0438] ·Life span (LT95) The resulting organic EL element has a current density of 50 mA / cm². 2 A voltage was applied to achieve the desired result, and the time it took for the brightness to reach 95% of the initial brightness (LT95 (unit: hours)) was measured. Brightness was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained measurements, "LT95 (relative value)" was calculated based on the following formula (Equation 1X). LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100 ... (Equation 1 x)

[0439] [Table 1]

[0440] The organic EL element of Example 1 contained a compound represented by general formula (1) as the host material for the first light-emitting layer. As a result, the organic EL element of Example 1 had a longer lifespan compared to the organic EL element of Comparative Example 1.

[0441] <Evaluation of Compounds> (Triplet energy T1) The compound to be measured was dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to prepare a solution, which was then placed in a quartz cell to be used as the measurement sample. For this sample, the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) was measured at a low temperature (77[K]). A tangent line was drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the energy amount T1 was calculated from the following conversion formula (F1) based on the wavelength value λedge[nm] at the intersection of the tangent line and the horizontal axis. The results are shown in Table 1. Note that the triplet energy T1 may have an error of approximately ±0.02 eV depending on the measurement conditions. Conversion formula (F1): T1[eV]=1239.85 / λedge

[0442] The tangent to the rise of the phosphorescence spectrum on the short-wavelength side is drawn as follows: When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum (i.e., the tangent at the inflection point) is considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurements, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer was used.

[0443] <Examples of synthesis> [Synthesis Example 1: Synthesis of Compound BH1-1] Compound BH1-1 was synthesized using the following synthetic route.

[0444] [ka]

[0445] (Synthesis of intermediate Ma) Under a nitrogen atmosphere, benzo[c]phenanthrene-5-ylboronic acid (145 g, 533 mmol), tetrakistriphenylphosphine (12.4 g, 10.7 mmol), sodium carbonate (113 g, 1066 mmol), 1,2-dimethoxyethane (3.3 L), and water (800 ml) were added to a 5 L three-necked flask and heated under reflux for 5 hours. The reaction solution was extracted with dichloromethane and then purified by column chromatography to obtain 117 g of a white solid. By ASAP-MS analysis, the white solid was identified as the intermediate Ma (yield 50%).

[0446] (Synthesis of intermediate Mb) Under a nitrogen atmosphere, intermediate Ma (117 g, 267 mmol) and tetrahydrofuran (1.2 L) were placed in a 2 L three-necked flask and cooled to 0°C. 1 M methylmagnesium bromide (800 mL) was added, and the mixture was heated under reflux for 7 hours. The reaction was quenched by adding aqueous ammonium chloride solution, and the mixture was extracted with dichloromethane. The resulting solution was concentrated and purified by silica gel chromatography to obtain 70 g of brown oil. ASAP-MS analysis identified the brown oil as intermediate Mb (yield 60%).

[0447] (Synthesis of intermediate Mc) Under a nitrogen atmosphere, intermediate Mb (70 g, 160 mmol) and chloroform (700 mL) were placed in a 2 L three-necked flask and cooled to 0°C. Boron trifluoride diethyl ether complex (98 g, 208 mmol) was added, and the mixture was stirred at room temperature to 35°C for 6 hours. After concentrating the reaction solution, it was extracted with dichloromethane and further purified by silica gel chromatography to obtain 34 g of a white solid. ASAP-MS analysis identified this white solid as intermediate Mc (yield 50%).

[0448] (Synthesis of compound BH1-1) Under a nitrogen atmosphere, intermediate Mc (4.2 g, 10 mmol), 1-pyreneboronic acid (2.58 g, 10.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (183 mg, 0.20 mmol), 2M sodium carbonate aqueous solution (12.5 mL, 25 mmol), and 1,4-dioxane (67 mL) were added to a 250 mL three-necked flask and heated under reflux for 5 hours. The reaction solution was extracted with dichloromethane and then purified by column chromatography to obtain 4.6 g of a white solid. By ASAP-MS analysis, the white solid was identified as compound BH1-1 (yield 84%).

[0449] [Synthesis Example 2: Synthesis of Compound BH1-2] Compound BH1-2 was synthesized using the following synthetic route.

[0450] [ka]

[0451] (Synthesis of compound BH1-2) Compound BH1-1 was synthesized using the same method as in the synthesis of compound BH1-1, except that intermediate Md was used instead of 1-pyreneboronic acid, yielding 4.69 g of a white solid. By ASAP-MS analysis, this white solid was identified as compound BH1-2 (yield 82%).

[0452] [Synthesis Example 3: Synthesis of Compound BH1-3] Compound BH1-3 was synthesized using the following synthetic route.

[0453] [ka]

[0454] (Synthesis of compound BH1-3) Compound BH1-1 was synthesized using the same method as before, except that 2-naphthaleneboronic acid was used instead of 1-pyreneboronic acid, yielding 3.29 g of a white solid. This white solid was identified as compound BH1-3 by ASAP-MS analysis (yield 70%).

[0455] [Synthesis Example 4: Synthesis of Compound BH-Ref1] Compound BH-Ref1 was synthesized using the following synthetic route.

[0456] [ka]

[0457] (Synthesis of compound BH-Ref1) Under a nitrogen atmosphere, 2-(13,13-dimethyl-13H-indeno[1,2-l]phenanthren-11-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.56 g, 8.47 mmol), 1-bromopyrene (2.38 g, 8.47 mmol), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (240 mg, 339 mmol), 2M aqueous sodium carbonate (12.7 mL), and 1,2-dimethoxyethane (100 mL) were placed in a 200 mL three-necked flask and stirred overnight at 70°C. The reaction mixture was extracted with toluene and concentrated. The resulting solid was purified by recrystallization and silica gel chromatography to obtain 1.5 g of a white solid. ASAP-MS analysis identified the white solid as compound BH-Ref1 (yield 36%). [Explanation of symbols]

[0458] 1A, 1B... Organic EL element, 2... Substrate, 3... Anode, 4... Cathode, 5A, 5B... Light-emitting region, 5... Light-emitting layer, 51... First light-emitting layer, 52... Second light-emitting layer, 6... Hole transport band, 61... Hole injection layer, 62... Hole transport layer, 7... Electron transport band, 71... Electron transport layer, 72... Electron injection layer.

Claims

1. A compound represented by the following general formula (1). 【Chemistry 1】 (In the above general formula (1), R １ and R ２ A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring １ and R ２ Each of them operates independently. Substituted or unsubstituted alkyl groups having 1 to 4 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ring A Ｘ This is a ring represented by the general formula (1A-1) or (1A-2), The ring represented by the general formula (1A-1) condenses with ring Cx at position a, The ring represented by the general formula (1A-2) is condensed with ring Cx at position b or c, Ring B Ｘ This is a ring represented by the general formula (1B-1), The ring represented by the general formula (1B-1) is condensed with ring Cx at positions d, e, f, or g. The ring represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1) each have, independently, one or more substituents represented by the following general formula (11) attached to them, or they do not have any substituents attached. At least one of the rings represented by the general formula (1A-1), the ring represented by the general formula (1A-2), and the ring represented by the general formula (1B-1) contains an aryl group Ar １ One or more are combined, Ar １ teeth, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, A substituted or unsubstituted benzofluoranthenyl group, (It is a substituted or unsubstituted perilenyl group.) 【Chemistry 2】 (In the above general formula (11), n １１ is 0, 1, 2, or 3, and L １１ teeth, Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, Substituted or unsubstituted benzofluoranthenyl groups, and A divalent arylene group derived by removing one hydrogen atom from the aryl ring of either a substituted or unsubstituted perilen group, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, L １１ The heterocyclic group includes at least one atom selected from the group consisting of oxygen, sulfur, silicon, phosphorus, and boron as a heteroatom. When n11 is 0, L １１ This represents a single bond, Ar １１ teeth, Is it a hydrogen atom? Substituted or unsubstituted phenyl groups, Substituted or unsubstituted biphenyl groups, Substituted or unsubstituted terphenyl groups, Substituted or unsubstituted naphthyl groups, Substituted or unsubstituted benzoantryl groups, Substituted or unsubstituted phenanthryl groups, Substituted or unsubstituted benzophenanthryl groups, Substituted or unsubstituted phenalenyl group, Substituted or unsubstituted pyrenyl group, Substituted or unsubstituted chrysenyl groups, Substituted or unsubstituted benzocrisenyl groups, Substituted or unsubstituted triphenylenyl groups, Substituted or unsubstituted benzotriphenylenyl group, Substituted or unsubstituted tetracenyl groups, Substituted or unsubstituted pentacenyl group, Substituted or unsubstituted fluorenyl groups, Substituted or unsubstituted 9,9'-spirobifluorenyl group, Substituted or unsubstituted benzofluorenyl groups, Substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups, A substituted or unsubstituted benzofluoranthenyl group, Either a substituted or unsubstituted perilenyl group, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Ar １１ The heterocyclic group includes at least one atom selected from the group consisting of oxygen, sulfur, silicon, phosphorus, and boron as a heteroatom. * indicates the bonding position.

2. The compound represented by the general formula (1) is a compound represented by the following general formulas (1C), (1D), (1E), or (1F): The compound according to claim 1. 【Transformation 3】 (In the above general formulas (1C), (1D), (1D), and (1F), R １ and R ２ Each of these independently corresponds to R in the general formula (1) above. １ and R ２ It is synonymous with, R ３ ~R １８ Each of them operates independently. The aryl group Ar １ , A substituent represented by the general formula (11), or It is a hydrogen atom, However, R ３ ~R １８ At least one of them is the aryl group Ar １ (That is the case.)

3. R １ and R ２ Each of these is independently a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. The compound according to claim 1 or claim 2.

4. R １ and R ２ These are, independently, a methyl group or an ethyl group. The compound according to any one of claims 1 to 3.

5. R １ and R ２ They do not bond with each other and do not form a ring. The compound according to any one of claims 1 to 4.

6. The aryl group Ar １ This is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted benzoanthryl group. The compound according to any one of claims 1 to 5.

7. Ar １１ One or more of the hydrogen atoms are deuterium atoms. The compound according to any one of claims 1 to 6.

8. L １１ A heterocyclic group is a divalent heterocyclic group with 5 to 16 substituted or unsubstituted ring-forming atoms. The compound according to any one of claims 1 to 7.

9. n11 is either 0 or 1. The compound according to any one of claims 1 to 8.

10. None of the rings represented by the general formula (1A-1), the rings represented by the general formula (1A-2), and the rings represented by the general formula (1B-1) are bonded to the substituent represented by the general formula (11). The compound according to any one of claims 1 to 9.

11. The groups described above as "substituted or unsubstituted" are all unsubstituted. Compound according to any one of claims 1 to 10

12. A compound comprising the compound described in any one of claims 1 to 11 as the first compound, Organic electroluminescent element.

13. Anode and, Cathode and, It comprises an organic layer disposed between the anode and the cathode, At least one layer of the organic layer contains the first compound, The organic electroluminescent element according to claim 12.

14. The organic layer has a light-emitting region, The light-emitting region includes a first light-emitting layer and a second light-emitting layer. The first light-emitting layer contains the first compound as the first host material. The organic electroluminescent element according to claim 13.

15. The first light-emitting layer comprises a first light-emitting compound, The first luminescent compound is a compound that exhibits luminescence with a maximum peak wavelength of 500 nm or less. The organic electroluminescent element according to claim 14.

16. The second light-emitting layer contains a second host material, The triplet energy T of the first host material １ (H1) and the triplet energy T of the second host material １ (H2) and satisfy the relationship shown in the following equation (Equation 1), The organic electroluminescent element according to claim 14 or claim 15. T １ (H1) > T １ (H2)…(Number 1)

17. A hole transport layer is provided between the anode and the light-emitting region. An organic electroluminescent element according to any one of claims 14 to 16.

18. An electron transport layer is provided between the cathode and the light-emitting region. An organic electroluminescent element according to any one of claims 14 to 17.

19. An electronic device equipped with an organic electroluminescent element according to any one of claims 12 to 18.

Images