Compounds, organic electroluminescent devices, and electronic equipment

Abstract

To provide compounds that can extend the life of organic electroluminescent devices and improve chromaticity.SOLUTION: For example, the compound is represented by the general formula (111) in the figure.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This 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%. To improve the performance of organic EL elements, for example, Patent Documents 1 to 5 have investigated compounds (e.g., pyrene compounds, etc.) used in organic EL elements. Furthermore, Patent Document 6 describes a phenomenon in which a singlet exciton is generated by the collision fusion of two triplet excitons (hereinafter sometimes referred to as Triplet-Triplet Fusion = TTF phenomenon) in order to improve the performance of organic EL elements. Examples of performance characteristics of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] International Publication No. 2021 / 049663 [Patent Document 2] Chinese Patent Application Publication No. 104650029 Specification [Patent Document 3] European Patent Application Publication No. 2463352 [Patent Document 4] U.S. Patent Application Publication No. 2009 / 0131673 [Patent Document 5] U.S. Patent Application Publication No. 2006 / 0240283 [Patent Document 6] International Publication No. 2010 / 134350 [Overview of the project] [Problems that the invention aims to solve]

[0004] For organic electroluminescent elements that emit blue fluorescence, there was a need to improve lifespan and suppress the deterioration of chromaticity.

[0005] An object of the present invention is to provide a compound that can extend the lifespan and improve the chromaticity of an organic electroluminescent element. Another object of the present invention is to provide an organic electroluminescent element with a long lifespan and improved chromaticity, and to provide an electronic device equipped with the organic electroluminescent element. [Means for solving the problem]

[0006] According to one aspect of the present invention, a compound represented by the following general formula (1) is provided.

[0007] [ka]

[0008] (In the above general formula (1), R1~R9, R 101 ~R 108 and R 111 ~R 118 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 20 carbon atoms, or These are heterocyclic groups with 5 to 21 substituted or unsubstituted ring-forming atoms. And, Ar 12 teeth, A substituted or unsubstituted ring-forming aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 9 to 31 ring-forming atoms, Ar 12 The substituted aryl group as is optionally substituted with a group selected from the group consisting of an aryl group having 6 to 20 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 21 ring-forming atoms, or not having any, Ar 12 The substituted heterocyclic group as is optionally substituted with at least one selected from the group consisting of an aryl group having 6 to 20 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 21 ring-forming atoms, or not having any, L 11 and L 12 are each independently, a single bond, a substituted or unsubstituted arylene group having 6 to 10 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring-forming atoms, p is 0 or 1, q is 0 or 1, p + q is 1 or 2. However, when p is 1, one of R 101 and R 102 , R 102 and R 103 , or R 103 and R 104 is a single bond bonded to *a, and the other of R 101 and R 102 , R 102 and R 103 , or R 103 and R 104 is a single bond bonded to *b, when q is 0, of the two selected from R 105 to R 108 one is a single bond bonded to *e and the other is a single bond bonded to *f, when q is 1, one of R 105 and R 106 , R 106 and R 107 , or R 107 and R 108One of them is a single bond that connects to *c, and R 105 and R 106 , R 106 and R 107 , or R 107 and R 108 The other side is a single bond that connects to *d, and not a single bond that connects to *c and *d. 105 ~R 108 , and R 115 ~R 118 Of the two selected, one is a single bond that connects to *e, and the other is a single bond that connects to *f.

[0009] According to one aspect of the present invention, an organic electroluminescent element is provided, comprising an anode, a cathode, and a light-emitting band disposed between the anode and the cathode, wherein the light-emitting band includes a first light-emitting layer containing a compound according to one aspect of the present invention as a first host material.

[0010] 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]

[0011] According to one aspect of the present invention, a compound can be provided that can extend the lifespan and improve the chromaticity of an organic electroluminescent element. According to one aspect of the present invention, an organic electroluminescent element with a long lifespan and improved chromaticity can be provided. According to one aspect of the present invention, an electronic device equipped with the organic electroluminescent element can be provided. [Brief explanation of the drawing]

[0012] [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. [Figure 3]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]

[0013] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0014] 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.

[0015] 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.

[0016] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself of a compound (e.g., monocyclic compound, condensed-ring compound, crosslinked compound, carbocyclic compound, and heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., monocyclic ring, condensed ring, and ring assembly). Atoms that do not constitute the ring (e.g., hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is the same unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Further, for example, the number of hydrogen atoms bonded to a carbon atom of a quinazoline ring or the number of atoms constituting a substituent is not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0017] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms", "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 the ZZ group 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.

[0018] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY atoms", "XX to YY atoms" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group 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, an unsubstituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of a "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been replaced by a substituent. The hydrogen atom in an "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. Also, in this specification, "substituted" in the case of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substituted" in the case of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group have been replaced by an AA group.

[0020] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.

[0021] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of an "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18. Unless otherwise specified in this specification, the number of ring-forming atoms of an "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkyl group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. Unless otherwise specified in this specification, the number of carbon atoms of an "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6. 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.

[0022] • "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.

[0023] • 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).

[0024] [ka]

[0025]

Chem.

[0026] ·Aryl group for substitution (specific example group G1B): o-Tolyl group, m-Tolyl group, p-Tolyl 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 in which one or more hydrogen atoms of a monovalent group derived from the ring structures represented by the general formulas (TEMP-1) to (TEMP-15) are replaced with substituents. <x

[0027] ·"Substituted or unsubstituted heterocyclic group" 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.

[0028] 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).

[0029] 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).

[0030] • 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.

[0031] • 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.

[0032] • 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), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphtobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0033] • 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 examples group G2A4):

[0034] [ka]

[0035] [ka]

[0036] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each of these is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH. In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A If at least one of the members is NH or CH2, the monovalent heterocyclic groups derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 members.

[0037] • Heterocyclic groups with substitutions containing a nitrogen atom (Specific examples 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.

[0038] • 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].

[0039] • 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].

[0040] • 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):

[0041] 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.

[0042] • "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.

[0043] • 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.

[0044] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0045] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has substituents, and examples of substituted alkenyl groups (Specific Example Group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include 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 substituent in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents.

[0046] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0047] • 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.

[0048] • "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.

[0049] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group.

[0050] • "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.

[0051] • 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.

[0052] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0053] · "-Si(R 901 )(R 902 )(R 903 ) a base represented by -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.

[0054] ·「-O-(R 904 ) a base represented by 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.

[0055] · "-S-(R 905 ) a base represented by 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.

[0056] · "-N(R 906 )(R 907 ) a base represented by -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), multiple G6s are either identical or different from one another.

[0057] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0058] • "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.

[0059] • "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.

[0060] • "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.

[0061] • "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.

[0062] • "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.

[0063] • "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.

[0064] • "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.

[0065] • "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.

[0066] 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.

[0067] 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.

[0068] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0069] [ka]

[0070] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0071] [ka]

[0072] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0073] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group specifically refer to any of the following groups:

[0074] [ka]

[0075] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0076] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0077] • "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.

[0078] • "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.

[0079] • "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.

[0080] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0081] [ka]

[0082] [ka]

[0083] 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.

[0084] [ka]

[0085] 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.

[0086] [ka]

[0087] 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.

[0088] 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).

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] [ka]

[0097] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0098] The above is a description of the substituents described herein.

[0099] • "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.

[0100] [ka]

[0101] For example, R921 ~R 930 Among the cases where "one or more sets consisting of two or more adjacent ones are combined with each other to form a ring", the set consisting of two adjacent ones that forms one set refers to R 921 and R 922 and the set of R 922 and R 923 and the set of R 923 and R 924 and the set of R 924 and R 930 and the set of R 930 and R 925 and the set of R 925 and R 926 and the set of R 926 and R 927 and the set of R 927 and R 928 and the set of R 928 and R 929 and the set of, and R 929 and R 921 and the set of.

[0102] The above "one or more sets" means that two or more sets consisting of two or more adjacent ones may form a ring at the same time. For example, R 921 and R 922 are combined with each other to form ring Q A , and at the same time R 925 and R 926 are combined with each other to form ring Q B is formed, then the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0103]

Chemical formula

[0104] The case where a "set consisting of two or more adjacent ones" forms a ring includes not only the case where a set consisting of "two" adjacent ones is combined as in the above example, but also the case where a set consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form ring Q A , and, 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.

[0105] [ka]

[0106] 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.

[0107] An "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. A "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocycle. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. A concrete example of an aromatic heterocycle is a structure in which the aromatic heterocycle group listed as a concrete example in concrete example group G2 is terminated by a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary elements. For example, as shown in the general formula (TEMP-104), 921 and R 922 A ring Q is formed when these two elements are bonded together. A R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 It refers to a ring formed by the carbon atoms of the anthracene skeleton to which the R atoms are bonded, and one or more arbitrary elements. A specific example is R 921 and R 922 And the environment Q A When forming R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by these two is a benzene ring.

[0108] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated with a hydrogen atom or the like, or substituted with "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. 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.

[0109] 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").

[0110] • 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 having 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.

[0111] 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.

[0112] 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.

[0113] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0114] 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.

[0115] 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.

[0116] In this specification, the expression "A≧B" means that the value of A is equal to the value of B, or that the value of A is greater than the value of B. In this specification, the expression "A ≤ B" means that the value of A is equal to the value of B, or that the value of A is less than the value of B.

[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), R1~R9, R 101 ~R 108 and R 111 ~R 118 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 20 carbon atoms, or These are heterocyclic groups with 5 to 21 substituted or unsubstituted ring-forming atoms. And, Ar 12 teeth, A substituted or unsubstituted ring-forming aryl group having 10 to 30 carbon atoms, or These are heterocyclic groups with 9 to 31 substituted or unsubstituted ring-forming atoms. Ar 12 A substituted aryl group may have or may not have at least one substituent selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 20 ring-forming carbon atoms and substituted or unsubstituted heterocyclic groups with 5 to 21 ring-forming atoms. Ar 12 A substituted heterocyclic group may have or may not have at least one substituent selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 20 ring-forming carbon atoms and substituted or unsubstituted heterocyclic groups with 5 to 21 ring-forming atoms. L 11 and L 12 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 10 carbon atoms, or A divalent heterocyclic group having 5 to 13 substituted or unsubstituted ring-forming atoms, p is either 0 or 1, q is either 0 or 1, p+q is either 1 or 2. however, When p is 1, R 101 and R 102 , R 102 and R 103 , or R 103 and R 104 One of them is a single bond that connects to *a, and R 101 and R 102 , R 102 and R 103 , or R 103 and R 104 The other side is a single bond that connects to *b, When q is 0, R 105 ~R 108 Of the two selected, one is a single bond that joins *e, and the other is a single bond that joins *f. When q is 1, R105 and R 106 , R 106 and R 107 , or R 107 and R 108 One of them is a single bond that connects to *c, and R 105 and R 106 , R 106 and R 107 , or R 107 and R 108 The other side is a single bond that connects to *d, and not a single bond that connects to *c and *d. 105 ~R 108 , and R 115 ~R 118 Of the two selected, one is a single bond that connects to *e, and the other is a single bond that connects to *f.

[0120] The compound according to this embodiment (the compound represented by the general formula (1)) has structures in its molecule represented by the following general formulas (1a), (1b), and (1c).

[0121] [ka]

[0122] [ka]

[0123] (In the above general formulas (1a), (1b), and (1c), R1 to R9, R 101 ~R 108 , R 111 ~R 118 Ar 12 , L 11 , L 12 p, q, *a, *b, *c, *d, *e, and *f are as defined in the general formula (1) above.

[0124] In the compound according to this embodiment, the structure represented by general formula (1a) (pyrene structure) is bonded to the structure represented by general formula (1c), and further, the structure represented by general formula (1c) is bonded to the structure represented by general formula (1b) (a condensed aryl structure with 10 or more ring-forming atoms or a condensed heterocyclic structure with 10 or more ring-forming atoms). Having such a molecular structure, the compound according to this embodiment has a singlet energy within a specific range (in one embodiment, a singlet energy of 2.95 eV or more and 3.25 eV or less), improving durability against excited states. Therefore, by using the compound according to this embodiment in the organic layer of an organic EL element, the lifespan of the organic EL element is extended. In the compound according to this embodiment, the structure represented by general formula (1a) (pyrene structure) and the structure represented by general formula (1b) (a condensed aryl structure with 10 or more ring-forming atoms or a condensed heterocyclic structure with 10 or more ring-forming atoms) are bonded to one of the same monorings in the structure represented by general formula (1c). As a result, the molecular shape of the compound according to this embodiment becomes round, and intermolecular interactions are suppressed. Therefore, by using the compound according to this embodiment in the organic layer of an organic EL element, an improvement in chromaticity can be expected.

[0125] In the compound according to this embodiment, when p is 1, "R 101 and R 102 , R 102 and R 103 , or R 103 and R 104 One of them is a single bond that connects to *a, and R 101 and R 102 , R 102 and R 103 , or R 103 and R 104 "The other side is a single bond that connects to *b" means, R 101 and R 102 One of them is a single bond that connects to *a, and R 101 and R 102 Is the other one a single bond that connects to *b? R 102 and R 103One of them is a single bond that connects to *a, and R 102 and R 103 The other side is a single bond that connects to *b, or R 103 and R 104 One of them is a single bond that connects to *a, and R 103 and R 104 This means that the other side is a single bond that connects to *b.

[0126] In the compound according to this embodiment, when q is 1, "R 105 and R 106 , R 106 and R 107 , or R 107 and R 108 One of them is a single bond that connects to *c, and R 105 and R 106 , R 106 and R 107 , or R 107 and R 108 "The other side is a single bond that connects to *d" means, R 105 and R 106 One of them is a single bond that connects to *c, and R 105 and R 106 Is the other one a single bond that connects to *d? R 106 and R 107 One of them is a single bond that connects to *c, and R 106 and R 107 The other side is a single bond that connects to *d, or R 107 and R 108 One of them is a single bond that connects to *c, and R 107 and R 108 This means that the other end is a single bond that connects to *d.

[0127] In this embodiment, the compound represented by general formula (1) is preferably represented by the following general formula (10).

[0128] [ka]

[0129] (In the above general formula (10), R1 to R9, R 101 ~R 108 , R 111 ~R 114 Ar 12 , L 11 , L 12 *a, *b, *e, and *f are as defined in the general formula (1) above.

[0130] In this embodiment, the compound represented by general formula (1) may also be represented by the following general formula (11).

[0131] [ka]

[0132] (In the above general formula (11), R1 to R9, R 101 ~R 107 , R 111 ~R 114 Ar 12 , L 11 , L 12 *a, *b, and *f are as defined in the general formula (1) above.

[0133] In this embodiment, R in the compound represented by general formula (1) 105 or R 106 However, it is preferable that the bond to *f is a single bond.

[0134] In this embodiment, R in the compound represented by general formula (1) 102 and R 103 One of them is a single bond that connects to *a, and R 102 and R 103 It is preferable that the other bond is a single bond that connects to *b.

[0135] In the above general formula (11), R 102 and R 103 One of them is a single bond that connects to *a, and R 102 and R 103When the other bond is a single bond to *b, the compound according to this embodiment is represented by the following general formula (111).

[0136] [ka]

[0137] (In the above general formula (111), R1 to R9, R 101 , R 104 , R 105 ~R 107 , R 111 ~R 114 Ar 12 , L 11 , L 12 And *f are defined as described in the general formula (1) above.

[0138] In this embodiment, R in the compound represented by general formula (1) 103 and R 104 One of them is a single bond that connects to *a, and R 103 and R 104 It is preferable that the other bond is a single bond that connects to *b.

[0139] In the above general formula (11), R 103 and R 104 One of them is a single bond that connects to *a, and R 103 and R 104 When the other bond is a single bond attached to *b, the compound according to this embodiment is represented by the following general formula (112).

[0140] [ka]

[0141] (In the above general formula (112), R1 to R9, R 101 , R 102 , R 105 ~R 107 , R 111 ~R 114 Ar 12 , L 11 , L12 And *f are defined as described in the general formula (1) above.

[0142] In this embodiment, Ar in the compound represented by general formula (1) 12 It is preferable that the group is an aryl group formed by the condensation of four or fewer monorings. In the compound according to this embodiment, Ar in the compound represented by general formula (1) 12 It is preferable that the group is an aryl group formed by the fusion of two, three, or four monorings.

[0143] In the first host material, for example, the pyrenyl group and the benzanthryl group are aryl groups formed by the fusion of four monorings (six-membered rings), the anthryl group and the phenanthryl group are aryl groups formed by the fusion of three monorings (six-membered rings), and the dibenzofuranyl group and the dibenzothienyl group are heterocyclic groups formed by the fusion of three monorings (two six-membered rings and one five-membered ring).

[0144] In this embodiment, Ar in the compound represented by general formula (1) 12 The aryl group may also preferably have an aryl group with 6 to 10 ring-forming carbon atoms as a substituent.

[0145] In this embodiment, Ar in the compound represented by general formula (1) 12 It is also preferable that the ring-forming aryl group has 10 to 30 carbon atoms and is unsubstituted.

[0146] In the compound according to this embodiment, Ar 12 It is also preferable that the group is represented by the following general formula (1100) or (1200).

[0147] [ka]

[0148] (In the above general formula (1100), R 1101 ~R 1110 One of them is L12 The binding position with L is shown. 12 R is not the bonding site with 1101 ~R 1110 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 having 6 to 17 carbon atoms, or It is a heterocyclic group with 5 to 17 ring-forming atoms, either substituted or unsubstituted.

[0149] In the compound according to this embodiment, Ar 12 It is also preferable that the group is represented by the following general formulas (1111), (1112), or (1113).

[0150] [ka]

[0151] (In the above general formulas (1111), (1112) and (1113), R 1101 ~R 1110 These are, respectively, R in the general formula (1100) above. 1101 ~R 1110 This is synonymous with L 12 (This indicates the bonding position.)

[0152] In the compound according to this embodiment, L 12 R is not the bonding site with 1101 ~R 1110 Each of these is preferably independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 10 ring-forming carbon atoms, and more preferably a hydrogen atom or a substituted or unsubstituted phenyl group.

[0153] [ka]

[0154] (In the above general formula (1200), R 1201 ~R 1212 One of them is L 12 The binding position with L is shown. 12 R is not the bonding site with 1201 ~R 1212 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 having 6 to 17 carbon atoms, or It is a heterocyclic group with 5 to 17 ring-forming atoms, either substituted or unsubstituted.

[0155] In the compound according to this embodiment, R in the general formula (1200) 1211 or R 1212 However, L 12 It is preferable that this is the bonding position.

[0156] In the compound according to this embodiment, R in the general formula (120) 1211 However, L 12 It is preferable that this is the bonding position.

[0157] In the compound according to this embodiment, Ar 12 It is also preferable that the group is represented by the following general formula (121) or general formula (122).

[0158] [ka]

[0159] (In the above general formulas (121) and (122), R 1201 ~R 1212 These are, respectively, R in the general formula (120) above. 1201 ~R 1212 This is synonymous with L 12 (This indicates the bonding position.)

[0160] In the compound according to this embodiment, L 12 R is not the bonding site with 1201 ~R 1212 Each of these is preferably independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 10 ring-forming carbon atoms, and more preferably a hydrogen atom or a substituted or unsubstituted phenyl group.

[0161] In the compound according to this embodiment, L 12 R is not the bonding site with 1101 ~R 1110 R 1201 ~R 1212 It is also preferable that it be a hydrogen atom.

[0162] In this embodiment, L in the compound represented by general formula (1) 11 It is also preferable that the ring-forming arylene group has 6 to 10 carbon atoms and is single-bonded, substituted, or unsubstituted.

[0163] In this embodiment, L in the compound represented by general formula (1) 11 It is also preferable that the bond be a single bond.

[0164] In this embodiment, L in the compound represented by general formula (1) 12 It is preferable that the ring-forming arylene group has 6 to 10 carbon atoms and is single-bonded, substituted, or unsubstituted.

[0165] In this embodiment, L in the compound represented by general formula (1) 12 It is preferable that the group is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0166] In this embodiment, R1 to R9 in the compound represented by general formula (1), and R that is not a single bond 101 ~R 108 , and R that is not a single bond 111 ~R 118Each of these is preferably independently a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 10 carbon atoms.

[0167] In this embodiment, R1 to R9 in the compound represented by general formula (1), and R that is not a single bond 101 ~R 108 , and R that is not a single bond 111 ~R 118 Preferably, it is a hydrogen atom.

[0168] In the compounds according to this embodiment, it is preferable that any group described as "substituted or unsubstituted" is an "unsubstituted" group.

[0169] (Method for producing the compound according to this embodiment) The compounds according to this embodiment can be produced by following the synthesis method described in the examples below, or by using known alternative reactions and raw materials tailored to the target product, in accordance with that synthesis method.

[0170] (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.

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[0240] [Second Embodiment] (Materials for organic electroluminescent devices) The material for an organic electroluminescent device according to this embodiment contains the compound according to the first embodiment. One embodiment is a material for an organic electroluminescent device that contains only the compound according to the first embodiment, and another embodiment is a material for an organic electroluminescent device that contains the compound according to the first embodiment and other compounds different from the compound in the first embodiment. In the organic electroluminescent element material of this embodiment, it is preferable that the compound according to the first embodiment is the host material. In this case, the material for the organic electroluminescent element may include the compound according to the first embodiment as the host material and other compounds, such as a luminescent compound as a dopant material.

[0241] [Third Embodiment] (Organic electroluminescent element) The organic electroluminescent element according to this embodiment has an anode, a cathode, and a light-emitting band disposed between the anode and the cathode.

[0242] The first light-emitting layer of the organic EL element according to this embodiment contains the compound according to the first embodiment (the compound represented by general formula (1)) as the first host material. As described above, the compound according to the first embodiment has improved durability against excited states and suppressed intermolecular interactions. Therefore, according to this embodiment, it is possible to provide an organic EL element with a longer lifespan and improved chromaticity.

[0243] (Emission band) The light-emitting band of the organic EL element according to this embodiment includes one or more light-emitting layers. In the organic EL element according to this embodiment, the light-emitting band includes a first light-emitting layer. In the organic EL element according to this embodiment, the first light-emitting layer contains the compound according to the first embodiment as a first host material.

[0244] In one embodiment of the organic EL element according to this embodiment, the light-emitting band includes only the first light-emitting layer. The organic EL element according to this embodiment may further include the first light-emitting layer and one or more organic layers. In one embodiment of the organic EL element according to this embodiment, the light-emitting band includes the first light-emitting layer and the second light-emitting layer.

[0245] (First light-emitting layer) In the organic EL element according to this embodiment, the first light-emitting layer preferably includes a first host material and a first light-emitting compound.

[0246] In the organic EL element according to this embodiment, it is preferable that the first luminescent compound exhibits emission with a maximum peak wavelength of 500 nm or less, and more preferably that it exhibits emission with a maximum peak wavelength of 480 nm or less. In the organic EL element according to this embodiment, the first luminescent compound preferably exhibits light emission with a maximum peak wavelength of 430 nm or higher.

[0247] In the organic EL element according to this embodiment, the first luminescent compound preferably exhibits fluorescence emission with a maximum peak wavelength of 500 nm or less, and more preferably exhibits fluorescence emission with a maximum peak wavelength of 480 nm or less. In the organic EL element according to this embodiment, the first luminescent compound preferably exhibits fluorescence emission with a maximum peak wavelength of 430 nm or higher.

[0248] In the organic EL element according to this embodiment, the first light-emitting compound is preferably a compound that does not contain an azine ring structure in its molecule.

[0249] In the organic EL element according to this embodiment, the first luminescent compound is preferably not a boron-containing complex, and more preferably not a complex.

[0250] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer does not contain a metal complex. Furthermore, in the organic EL element according to this embodiment, it is also preferable that the first light-emitting layer does not contain a boron-containing complex.

[0251] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer does not contain a phosphorescent material (dopant material). Furthermore, it is preferable that the first light-emitting layer does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0252] The method for measuring the maximum peak wavelength of a compound is as follows: Prepare a 5 μmol / L toluene solution of the compound to be measured, place it in a quartz cell, and measure the emission spectrum of the sample at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrofluorometer (instrument 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 peak wavelength. In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum fluorescence emission peak wavelength (FL-peak).

[0253] In the emission spectrum of the first luminescent compound, the peak with the maximum emission intensity is defined as the maximum peak, and when the height of this maximum peak is set to 1, it is preferable that the heights of the other peaks appearing in the emission spectrum are less than 0.6. The peaks in the emission spectrum are defined as the maximum values. Furthermore, it is preferable that the emission spectrum of the first luminescent compound has fewer than three peaks.

[0254] In the organic EL element according to this embodiment, it is preferable that the triplet energy T1(H1) of the first host material and the triplet energy T1(D1) of the first luminescent compound satisfy the following equation (Equation 6). T1(D1)>T1(H1) …(Math 6)

[0255] Because the first host material and the first luminescent compound satisfy the relationship shown in equation (Equation 6), triplet excitons generated on the first host material do not move to the first luminescent compound, which has a higher triplet energy. Furthermore, triplet excitons generated on the first luminescent compound rapidly transfer energy to the molecules of the first host material. In other words, singlet excitons are efficiently generated on the first host material by the TTF phenomenon through collisions between triplet excitons without the triplet excitons from the first host material moving to the first luminescent compound.

[0256] In the organic EL element according to this embodiment, it is preferable that the singlet energy S1(H1) of the first host material and the singlet energy S1(D1) of the first luminescent compound satisfy the relationship shown in the following formula (Equation 5). The singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state. S1(H1)>S1(D1) …(Math 5)

[0257] When the first host material and the first luminescent compound satisfy the relationship shown in equation (Equation 5), singlet excitons generated on the first host material can easily transfer energy from the first host material to the first luminescent compound, contributing to the fluorescence emission of the first luminescent compound.

[0258] In the organic EL element according to this embodiment, the first luminescent compound is preferably contained in the first light-emitting layer in an amount of 0.5% by mass or more. That is, the first light-emitting layer preferably contains the first luminescent compound in an amount of 0.5% by mass or more of the total mass of the first light-emitting layer, more preferably in an amount of 1.0% by mass or more of the total mass of the first light-emitting layer, even more preferably in an amount of 1.2% by mass or more of the total mass of the first light-emitting layer, and even more preferably in an amount of 1.5% by mass or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first light-emitting compound in an amount of 10% by mass or less of the total mass of the first light-emitting layer, more preferably in an amount of 7% by mass or less of the total mass of the first light-emitting layer, and even more preferably in an amount of 5% by mass or less of the total mass of the first light-emitting layer.

[0259] In the organic EL element according to this embodiment, the first light-emitting layer preferably contains the first host material in an amount of 60% by mass or more of the total mass of the first light-emitting layer, more preferably 70% by mass or more of the total mass of the first light-emitting layer, even more preferably 80% by mass or more of the total mass of the first light-emitting layer, even more preferably 90% by mass or more of the total mass of the first light-emitting layer, and still more preferably 95% by mass or more of the total mass of the first light-emitting layer. The first light-emitting layer preferably contains the first host material in an amount of 99% by mass or less of the total mass of the first light-emitting layer. However, if the first light-emitting layer contains a first host material and a first light-emitting compound, the upper limit of the total content of the first host material and the first light-emitting compound is 100% by mass.

[0260] This embodiment does not exclude the first light-emitting layer from containing materials other than the first host material and the first light-emitting compound. The first light-emitting layer may contain only one type of first host material, or two or more types. The first light-emitting layer may contain only one type of first light-emitting compound, or two or more types.

[0261] (Second light-emitting layer) In the organic EL element according to this embodiment, the light-emitting band may further preferably include a second light-emitting layer.

[0262] In the organic EL element according to this embodiment, the second light-emitting layer preferably contains a second host material. The second host material is a different compound from the first host material contained in the first light-emitting layer.

[0263] In the organic EL element according to this embodiment, the second light-emitting layer preferably includes a second host material and a second light-emitting compound. In the organic EL element according to this embodiment, the first light-emitting compound and the second light-emitting compound are either the same or different from each other.

[0264] In the organic EL element according to this embodiment, it is preferable that the second luminescent compound exhibits luminescence with a maximum peak wavelength of 500 nm or less. The first luminescent compound and the second luminescent compound are each compounds that independently exhibit luminescence with a maximum peak wavelength of 500 nm or less.

[0265] In the organic EL element according to this embodiment, the second luminescent compound preferably exhibits emission with a maximum peak wavelength of 480 nm or less, and more preferably exhibits emission with a maximum peak wavelength of 430 nm or more.

[0266] In the organic EL element according to this embodiment, the second luminescent compound preferably exhibits fluorescence emission with a maximum peak wavelength of 500 nm or less, and more preferably exhibits fluorescence emission with a maximum peak wavelength of 480 nm or less. In the organic EL element according to this embodiment, the second luminescent compound preferably exhibits fluorescence emission with a maximum peak wavelength of 430 nm or higher. The method for measuring the maximum peak wavelength of a compound is as described above.

[0267] In the organic EL element according to this embodiment, it is preferable that the full width at half maximum of the largest peak of the second luminescent compound is 1 nm or more and 20 nm or less.

[0268] In the organic EL element according to this embodiment, the light-emitting band includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer includes a first host material and a first light-emitting compound, the second light-emitting layer includes a second host material and a second light-emitting compound, the first host material and the second host material are different from each other, and the first light-emitting compound and the second light-emitting compound are either the same or different from each other.

[0269] In the organic EL element according to this embodiment, it is preferable that 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)

[0270] According to one aspect of this embodiment, an organic electroluminescent element with improved luminescence efficiency can be provided. Conventionally, Triplet-Triplet-Annhilation (sometimes referred to as TTA) is known as a technique for improving the luminescence efficiency of organic electroluminescent devices. TTA is a mechanism in which triplet excitons collide with other triplet excitons to generate singlet excitons. The TTA mechanism is sometimes referred to as the TTF mechanism, as described in Patent Document 6.

[0271] 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%.

[0272] According to one aspect of this embodiment of the organic electroluminescent element, triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer are less likely to be quenched at the interface between the first light-emitting layer and the organic layer in direct contact with the first light-emitting layer, 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 an excess of 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 an excess of holes is possible. An organic electroluminescent element according to one aspect of this embodiment comprises at least two light-emitting layers (i.e., a first light-emitting layer and a second light-emitting layer) that satisfy a predetermined relationship, wherein the triplet energy T1(H1) of the first host material in the first light-emitting layer and the triplet energy T1(H2) of the second host material in the second light-emitting layer satisfy the relationship given by the formula (Equation 1). By providing a first and second light-emitting layer that satisfy the relationship in the above formula (Equation 1), triplet excitons generated in the first light-emitting layer can move to the second light-emitting layer without being quenched by excess carriers, and the reverse movement from the second light-emitting layer to the first light-emitting layer can be suppressed. As a result, the TTF mechanism is activated in the second light-emitting layer, singlet excitons are efficiently generated, and the luminescence efficiency is improved. Thus, the organic electroluminescent element comprises a first light-emitting layer that primarily generates triplet excitons and a second light-emitting layer that primarily exhibits the TTF mechanism by utilizing triplet excitons migrated from the first light-emitting layer, as separate regions. By using a compound with a lower triplet energy than the first host material in the first light-emitting layer as the second host material in the second light-emitting layer, a difference in triplet energy is created, thereby improving the luminescence efficiency.

[0273] In the organic EL element according to this embodiment, it is preferable that 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 1B). T1(H1)-T1(H2)>0.03eV …(Math 1B)

[0274] In this specification, "host material" refers to a material that is included in the layer in an amount of, for example, "50% by mass or more". Therefore, the first light-emitting layer contains, for example, the first host material in an amount of 50% by mass or more of the total mass of the first light-emitting layer. The second light-emitting layer contains, for example, the second host material in an amount of 50% by mass or more of the total mass of the second light-emitting layer.

[0275] In the organic EL element according to this embodiment, when the light emission band includes a first light-emitting layer and a second light-emitting layer, the first host material and the first light-emitting compound satisfy the relationship shown in formula (Equation 6). As a result, triplet excitons generated in the first light-emitting layer move over the first host material rather than the first light-emitting compound which has a higher triplet energy, making it easier for them to move to the second light-emitting layer.

[0276] In this embodiment, when the light emission band includes a first light-emitting layer and a second light-emitting layer, it is preferable that the following equation (Equation 20B) is satisfied for the organic EL element. T1(D1)>T1(H1)>T1(H2) …(Math 20B)

[0277] In the organic EL element according to this embodiment, it is preferable that the singlet energy S1(H2) of the second host material and the singlet energy S1(D2) of the second luminescent compound satisfy the following relationship (Equation 7). S1(H2)>S1(D2)…(Number 7)

[0278] In the organic EL element according to this embodiment, the second luminescent compound and the second host material satisfy the relationship shown in equation (Equation 7). As a result, the singlet energy of the second luminescent compound is smaller than the singlet energy of the second host material. Therefore, singlet excitons generated by the TTF phenomenon transfer energy from the second host material to the second luminescent compound, contributing to the fluorescence emission of the second luminescent compound.

[0279] In the organic EL element according to this embodiment, it is preferable that the triplet energy T1(D2) of the second luminescent compound and the triplet energy T1(H2) of the second host material satisfy the following equation (Equation 8). T1(D2)>T1(H2) …(Math 8)

[0280] In the organic EL element according to this embodiment, the relationship between the second luminescent compound and the second host material satisfies the relationship shown in equation (Equation 8). As a result, when triplet excitons generated in the first light-emitting layer move to the second light-emitting layer, they transfer energy to the molecules of the second host material rather than to the second luminescent compound, which has a higher triplet energy. Furthermore, triplet excitons generated by the recombination of holes and electrons on the second host material do not move to the second luminescent compound, which has a higher triplet energy. Triplet excitons generated by recombination on the molecules of the second luminescent compound rapidly transfer energy to the molecules of the second host material. Without the triplet excitons from the second host material moving to the second luminescent compound, the triplet excitons efficiently collide with each other on the second host material via the TTF phenomenon, generating singlet excitons.

[0281] In the organic EL element according to this embodiment, the second light-emitting compound is preferably a compound that does not contain an azine ring structure in its molecule.

[0282] In the organic EL element according to this embodiment, the second luminescent compound is preferably not a boron-containing complex, and more preferably not a complex.

[0283] In the organic EL element according to this embodiment, it is preferable that the second light-emitting layer does not contain a metal complex. Furthermore, in the organic EL element according to this embodiment, it is also preferable that the second light-emitting layer does not contain a boron-containing complex.

[0284] In the organic EL element according to this embodiment, it is preferable that the second light-emitting layer does not contain a phosphorescent material (dopant material). Furthermore, it is preferable that the second light-emitting layer does not contain heavy metal complexes or phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0285] In the organic EL element according to this embodiment, the second luminescent compound is preferably contained in the second light-emitting layer in an amount of 0.5% by mass or more. That is, the second light-emitting layer preferably contains the second luminescent compound in an amount of 0.5% by mass or more of the total mass of the second light-emitting layer, more preferably in an amount of 1.0% by mass or more of the total mass of the second light-emitting layer, even more preferably in an amount of 1.2% by mass or more of the total mass of the second light-emitting layer, and even more preferably in an amount of 1.5% by mass or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second light-emitting compound in an amount of 10% by mass or less of the total mass of the second light-emitting layer, more preferably in an amount of 7% by mass or less of the total mass of the second light-emitting layer, and even more preferably in an amount of 5% by mass or less of the total mass of the second light-emitting layer.

[0286] The second light-emitting layer preferably contains the second compound as the second host material in an amount of 60% by mass or more of the total mass of the second light-emitting layer, more preferably 70% by mass or more of the total mass of the second light-emitting layer, even more preferably 80% by mass or more of the total mass of the second light-emitting layer, even more preferably 90% by mass or more of the total mass of the second light-emitting layer, and still more preferably 95% by mass or more of the total mass of the second light-emitting layer. The second light-emitting layer preferably contains the second host material in an amount of 99% by mass or less of the total mass of the second light-emitting layer. If the second light-emitting layer contains a second host material and a second light-emitting compound, the upper limit of the total content of the second host material and the second light-emitting compound is 100% by mass.

[0287] This embodiment does not exclude the possibility that the second light-emitting layer includes materials other than the second host material and the second light-emitting compound. The second light-emitting layer may contain only one type of second host material or two or more types of second host materials. The second light-emitting layer may contain only one type of second light-emitting compound or two or more types of second light-emitting compounds.

[0288] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1(DX) of the first light-emitting compound or the second light-emitting compound, the triplet energy T1(H1) of the first host material, and the triplet energy T1(H2) of the second host material satisfy the relationship of the following formula (Formula 10). 2.6 eV > T1(DX) > T1(H1) > T1(H2) …(Formula 10)

[0289] The triplet energy T1(D1) of the first light-emitting compound preferably satisfies the relationship of the following formula (Formula 10A). 2.6 eV > T1(D1) > T1(H1) > T1(H2) …(Formula 10A)

[0290] The triplet energy T1(D2) of the second light-emitting compound preferably satisfies the relationship of the following formula (Formula 10B). 2.6 eV > T1(D2) > T1(H1) > T1(H2) …(Formula 10B)

[0291] In the organic EL device according to the present embodiment, it is preferable that the triplet energy T1(DX) of the first light-emitting compound or the second light-emitting compound and the triplet energy T1(H1) of the first host material satisfy the relationship of the following formula (Formula 11). 0 eV < T1(DX) - T1(H1) < 0.6 eV …(Formula 11)

[0292] The triplet energy T1(D1) of the first light-emitting compound preferably satisfies the relationship of the following formula (Formula 11A). 0 eV < T1(D1) - T1(H1) < 0.6 eV …(Formula 11A)

[0293] The triplet energy T1(D2) of the second light-emitting compound preferably satisfies the relationship of the following formula (Formula 11B). 0 eV < T1(D2) - T1(H2) < 0.8 eV …(Equation 11B)

[0294] In the organic EL device according to this embodiment, it is preferable that the triplet energy T1(H1) of the first host material satisfies the relationship of the following mathematical formula (Equation 12). T1(H1) > 2.0 eV …(Equation 12)

[0295] In the organic EL device according to this embodiment, it is also preferable that the triplet energy T1(H1) of the first host material satisfies the relationship of the following mathematical formula (Equation 12A), and the following mathematical formula (Equation 12B) is also preferably satisfied. T1(H1) > 2.10 eV …(Equation 12A) T1(H1) > 2.15 eV …(Equation 12B)

[0296] In the organic EL device according to this embodiment, when the triplet energy T1(H1) of the first host material satisfies the relationship of the above-mentioned mathematical formula (Equation 12A) or the above-mentioned mathematical formula (Equation 12B), the triplet excitons generated in the first light-emitting layer are likely to move to the second light-emitting layer, and it is also likely to suppress the reverse movement from the second light-emitting layer to the first light-emitting layer. As a result, singlet excitons are efficiently generated in the second light-emitting layer, and the luminous efficiency is improved.

[0297] In the organic EL device according to this embodiment, it is also preferable that the triplet energy T1(H1) of the first host material satisfies the relationship of the following mathematical formula (Equation 12C), and it is also preferable that the triplet energy T1(H1) satisfies the relationship of the following mathematical formula (Equation 12D). 2.08 eV > T1(H1) > 1.87 eV …(Equation 12C) 2.05 eV > T1(H1) > 1.90 eV …(Equation 12D)

[0298] In the organic EL device according to this embodiment, when the triplet energy T1(H1) of the first host material satisfies the relationship of the above-mentioned mathematical formula (Equation 12C) or the above-mentioned mathematical formula (Equation 12D), the energy of the triplet excitons generated in the first light-emitting layer becomes smaller, and a long life of the organic EL device can be expected.

[0299] In the organic EL element according to this embodiment, it is preferable that the triplet energy T1(D1) of the first light-emitting compound satisfies the relationship shown in the following formula (Equation 14A), and also preferable that it satisfies the relationship shown in the following formula (Equation 14B). 2.60eV>T1(D1) …(Calculus 14A) 2.50eV>T1(D1) …(Math 14B) The organic EL element has a longer lifespan because the first light-emitting layer contains a first light-emitting compound that satisfies the relationship in the formula (Equation 14A) or (Equation 14B).

[0300] In the organic EL element according to this embodiment, it is preferable that the triplet energy T1(D2) of the second luminescent compound satisfies the relationship shown in the following formula (Equation 14C), and it is also preferable that it satisfies the relationship shown in the following formula (Equation 14D). 2.60eV>T1(D2)…(Number 14C) 2.50eV>T1(D2) …(Calculus 14D) The second light-emitting layer contains a compound that satisfies the relationship in the above formula (Equation 14C) or (Equation 14D), thereby extending the lifespan of the organic EL element.

[0301] In the organic EL element according to this embodiment, it is also preferable that the triplet energy T1(H2) of the second host material satisfies the relationship shown in the following formula (Equation 13). T1(H2)>1.9eV …(Math 13)

[0302] In the organic EL element according to this embodiment, it is also preferable that the triplet energy T1(H2) of the second host material satisfies the following equation (Equation 13A). 1.9eV≧T1(H2)≧1.8eV …(Math 13A)

[0303] In the organic EL element according to this embodiment, it is also preferable that the first light-emitting layer is placed between the anode and the second light-emitting layer.

[0304] In the organic EL element of this embodiment, it is also preferable that the second light-emitting layer is placed between the anode and the first light-emitting layer.

[0305] In the organic EL element according to this embodiment, it is preferable that one of the first light-emitting layer and the second light-emitting layer is the layer located furthest to the anode among a plurality of layers having a light-emitting band.

[0306] In the organic EL element according to this embodiment, it is preferable that one of the first light-emitting layer and the second light-emitting layer is the layer located furthest to the cathode among a plurality of layers having a light-emitting band.

[0307] The organic EL element according to this embodiment may have an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order, or the order of the first and second light-emitting layers may be reversed. That is, it may have an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order. In either case of the order of the first and second light-emitting layers, by selecting a combination of materials that satisfies the relationship in the above formula (Equation 1), the effects of a laminated configuration of the first and second light-emitting layers can be expected.

[0308] In the organic EL element according to this embodiment, when 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, the electron mobility μe(H1) of the first host material and the electron mobility μe(H2) of the second host material satisfy the relationship shown in the following formula (Equation 30). μe(H2) > μe(H1) …(Equation 30) The first host material and the second host material satisfy the relationship shown in the above formula (Equation 30), thereby improving the recombination ability of holes and electrons in the first light-emitting layer.

[0309] In the organic EL element according to this embodiment, when 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 also preferable that the hole mobility μh(H1) of the first host material and the hole mobility μh(H2) of the second host material satisfy the relationship shown in the following formula (Equation 31). μh(H1) > μh(H2) …(Equation 31)

[0310] In the organic EL element according to this embodiment, when 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 also preferable that the hole mobility μh(H1) of the first host material, the electron mobility μe(H1) of the first host material, the hole mobility μh(H2) of the second host material, and the electron mobility μe(H2) of the second host material satisfy the relationship shown in the following formula (Equation 32). (μe(H2) / μh(H2))>(μe(H1) / μh(H1)) …(Math. 32)

[0311] Electron mobility can be measured by impedance measurement using a mobility evaluation element fabricated according to the following procedure. The mobility evaluation element is fabricated, for example, according to the following procedure. A layer for measuring electron mobility is formed by depositing compound Target onto a glass substrate with an aluminum electrode (anode), covering the aluminum electrode. On this layer, compound ET-A is deposited to form an electron transport layer. On top of this electron transport layer, LiF is deposited to form an electron injection layer. On top of this electron injection layer, metallic aluminum (Al) is deposited to form a metallic cathode. The above-mentioned configuration of elements for mobility evaluation can be summarized as follows: glass / Al(50) / Target(200) / ET-A(10) / LiF(1) / Al(50) The numbers in parentheses indicate the film thickness (nm).

[0312] [ka]

[0313] An element for evaluating electron mobility is installed in an impedance measuring device, and impedance measurements are performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. From the measured impedance Z, the modulus M is calculated using the following formula (C1). Calculation formula (C1): M=jωZ In the above formula (C1), j is the imaginary unit whose square is -1, and ω is the angular frequency [rad / s]. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is calculated from the frequency fmax, which shows the peak, using the following formula (C2). Calculation formula (C2): τ=1 / (2πfmax) In the above calculation formula (C2), π is the symbol representing the ratio of a circle's circumference to its diameter (pi). Using the above τ, the electron mobility μe is calculated from the following formula (C3-1). Calculation formula (C3-1):μe=d 2 / (Vτ) In the above calculation formula (C3-1), d is the total thickness of the organic thin film constituting the device, and in the case of a device configuration for evaluating electron mobility, d = 210 [nm].

[0314] Hole mobility can be measured by impedance measurement using a mobility evaluation element fabricated according to the following procedure. The mobility evaluation element is fabricated, for example, according to the following procedure. On a glass substrate with an ITO transparent electrode (anode), the compound HA-2 is deposited to cover the transparent electrode, forming a hole injection layer. On top of this hole injection layer, the compound HT-A is deposited to form a hole transport layer. Subsequently, the compound Target, whose hole mobility is to be measured, is deposited to form a measurement target layer. On top of this measurement target layer, metallic aluminum (Al) is deposited to form a metallic cathode. The above-mentioned configuration of elements for mobility evaluation can be summarized as follows: ITO(130) / HA-2(5) / HT-A(10) / Target(200) / Al(80) The numbers in parentheses indicate the film thickness (nm).

[0315] [ka]

[0316] An element for evaluating hole mobility is installed in an impedance measuring device, and impedance measurement is performed. The impedance measurement is performed by sweeping the measurement frequency from 1 Hz to 1 MHz. At that time, a DC voltage V is applied to the element simultaneously with an AC amplitude of 0.1 V. From the measured impedance Z, the modulus M is calculated using the relationship of the calculation formula (C1) above. In a Bode plot with the imaginary part of the modulus M on the vertical axis and frequency [Hz] on the horizontal axis, the electrical time constant τ of the mobility evaluation element is determined from the frequency fmax, which shows a peak, using the calculation formula (C2) described above. Using the τ obtained from the above calculation formula (C2), the hole mobility μh is calculated from the relationship in the following calculation formula (C3-2). Calculation formula (C3-2):μh=d 2 / (Vτ) In the above calculation formula (C3-2), d is the total thickness of the organic thin film constituting the device, and in the case of a device configuration for evaluating hole mobility, d = 215 [nm].

[0317] In this specification, electron mobility and hole mobility are defined as the square root of the electric field strength E. 1 / 2 =500[V 1 / 2 / cm 1 / 2 This is the value at the time of ]. The square root of the electric field strength E 1 / 2 This can be calculated from the relationship shown in the following formula (C4). Calculation formula (C4): E 1 / 2 =V 1 / 2 / d 1 / 2 For the impedance measurement described above, Solartron's Model 1260 impedance measuring device is used, and for higher accuracy, Solartron's Model 1296 dielectric constant measurement interface can also be used in conjunction with it.

[0318] In the organic EL element according to this embodiment, it is preferable that the first light-emitting layer and the second light-emitting layer are in direct contact.

[0319] In this specification, the layer structure in which "the first light-emitting layer and the second light-emitting layer are in direct contact" may also include, for example, any of the following embodiments (LS1), (LS2), and (LS3). (LS1) A configuration in which, during the process of depositing a compound for the first light-emitting layer and depositing a compound for the second light-emitting layer, a region is created in which both the first host material and the second host material are mixed, and this region is located at the interface between the first light-emitting layer and the second light-emitting layer. (LS2) In a configuration in which the first light-emitting layer and the second light-emitting layer 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 created during the process of vapor deposition of the compound relating to the first light-emitting layer and the vapor deposition of the compound relating to the second light-emitting layer, and this region is located at the interface between the first light-emitting layer and the second light-emitting layer. (LS3) A configuration in which, when the first light-emitting layer and the second light-emitting layer 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 and the vapor deposition of the compound relating to the second light-emitting layer, and such region is located at the interface between the first light-emitting layer and the second light-emitting layer.

[0320] (Second host material) In the organic EL element according to this embodiment, the second host material is not particularly limited, but examples include a second compound represented by the following general formula (2).

[0321] (Second compound) In the organic EL element according to this embodiment, the second compound is preferably a compound represented by the following general formula (2). The second host material is preferably a second compound represented by the following general formula (2).

[0322] [ka]

[0323] (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 having 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 having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0324] (In the second host material, 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 having 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 from one another. R 801 If multiple R 801They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.

[0325] In the organic EL element according to this embodiment, 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, or It is a nitro group, 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 having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0326] In the organic EL element according to this embodiment, L 201 and L 202 Each of these is independently a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, and Ar 201 and Ar 202 Preferably, each of these is independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms.

[0327] In the organic EL element according to this embodiment, Ar 201 and Ar 202 Each of these groups is preferably independently a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.

[0328] In the organic EL element according to this embodiment, the second compound represented by general formula (2) is preferably a compound represented by the following general formulas (201), (202), (203), (204), (205), (206), (207), (208), or (209).

[0329] [ka]

[0330] [ka]

[0331] [ka]

[0332] [ka]

[0333] [ka]

[0334] [ka]

[0335] [ka]

[0336] [ka]

[0337] [ka]

[0338] (In the above general formulas (201) to (209), L 201 and Ar 201 L in the general formula (2) above is 201 and Ar 201 It is synonymous with, R 201 ~R 208 Each of these independently corresponds to R in the general formula (2) above. 201 ~R 208 (This is synonymous with...)

[0339] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formulas (221), (222), (223), (224), (225), (226), (227), (228), or (229).

[0340] [ka]

[0341] [ka]

[0342] [ka]

[0343] [ka]

[0344] [ka]

[0345] [ka]

[0346] [ka]

[0347] [ka]

[0348] [ka]

[0349] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229), R 201R 203 ~R 208 Each of these independently corresponds to R in the general formula (2) above. 201 R 203 ~R 208 It is synonymous with, L 201 and Ar 201 These are, respectively, L in the general formula (2) above. 201 and Ar 201 It is synonymous with, L 203 L in the general formula (2) above is 201 It is synonymous with, L 203 and L 201 They are either identical or different from each other. Ar 203 This is Ar in the general formula (2) above. 201 It is synonymous with, Ar 203 and Ar 201 They are either identical or different to one another.

[0350] The second compound represented by the general formula (2) is also preferably a compound represented by the following general formulas (241), (242), (243), (244), (245), (246), (247), (248), or (249).

[0351] [ka]

[0352] [ka]

[0353] [ka]

[0354] [ka]

[0355] [ka]

[0356] [ka]

[0357] [ka]

[0358] [ka]

[0359] [ka]

[0360] (In the above general formulas (241), (242), (243), (244), (245), (246), (247), (248), and (249), R 201 , R 202 R 204 ~R 208 Each of these independently corresponds to R in the general formula (2) above. 201 , R 202 R 204 ~R 208 It is synonymous with, L 201 and Ar 201 These are, respectively, L in the general formula (2) above. 201 and Ar 201 It is synonymous with, L 203 L in the general formula (2) above is 201 It is synonymous with, L 203 and L 201 They are either identical or different from each other. Ar203 This is Ar in the general formula (2) above. 201 It is synonymous with, Ar 203 and Ar 201 They are either identical or different to one another.

[0361] In the second compound represented by the general formula (2) above, R 201 ~R 208 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or -Si(R 901 )(R 902 )(R 903 It is preferable that the group is represented by ).

[0362] L 201 This is a single-bonded or unsubstituted ring-forming arylene group with 6 to 22 carbon atoms, and Ar 201 It is preferable that the ring-forming aryl group has 6 to 22 carbon atoms and is either substituted or unsubstituted.

[0363] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R is a substituent of the anthracene skeleton. 201 ~R 208 It is preferable that the atom is a hydrogen atom in order to prevent the suppression of intermolecular interactions and to suppress the decrease in electron mobility, 201 ~R 208 This may be a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 ring-forming atoms. R 201 ~R 208When the substituent is a bulky alkyl group or cycloalkyl group, intermolecular interactions are suppressed, reducing electron mobility to the first host material, and potentially failing to satisfy the relationship μe(H2)>μe(H1) described in formula (Equation 30). When the second compound is used as the second light-emitting layer, it is expected that the relationship μe(H2)>μe(H1) will be satisfied, thereby suppressing the decrease in the recombination ability of holes and electrons in the first light-emitting layer and the decrease in luminescence efficiency. The substituents include haloalkyl groups, alkenyl groups, alkynyl groups, and -Si(R 901 )(R 902 )(R 903 A group represented by -O-(R 904 A group represented by -S-(R 905 A group represented by -N(R 906 )(R 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 The groups represented by, halogen atoms, cyano groups, and nitro groups may become bulkier, and alkyl groups and cycloalkyl groups may become even bulkier. In the second compound represented by the general formula (2), R is a substituent of the anthracene skeleton. 201 ~R 208 Preferably, the substituent is not bulky, and is not alkyl or cycloalkyl group, but alkyl, cycloalkyl, haloalkyl, alkenyl group, alkynyl group, -Si(R 901 )(R 902 )(R 903 A group represented by -O-(R 904 A group represented by -S-(R 905 A group represented by -N(R 906 )(R 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 It is more preferable that the group is not a halogen atom, a cyano group, or a nitro group.

[0364] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R201 ~R 208 Each of these independently consists of a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or -Si(R 901 )(R 902 )(R 903 It is also preferable that the group be represented by ).

[0365] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 Preferably, it is a hydrogen atom.

[0366] In the second compound, R 201 ~R 208 In the case of "substituted or unsubstituted" in the above, it is preferable that the substituents do not include the substituents that may increase bulk as described above, particularly substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. 201 ~R 208 In the case of "substituted or unsubstituted" in this context, the substituents do not include substituted or unsubstituted alkyl groups and substituted or unsubstituted cycloalkyl groups. This prevents the suppression of intermolecular interactions caused by the presence of bulky substituents such as alkyl and cycloalkyl groups, thereby preventing a decrease in electron mobility. Furthermore, when such a second compound is used as the second light-emitting layer, it is possible to suppress a decrease in the recombination ability of holes and electrons in the first light-emitting layer, as well as a decrease in luminescence efficiency.

[0367] R is a substituent on the anthracene skeleton. 201 ~R 208 However, R is not a bulky substituent, but rather a substituent. 201 ~R 208 It is even more preferable that it is unsubstituted. Also, R, which is a substituent on the anthracene skeleton. 201 ~R 208 When R is not a bulky substituent, 201 ~R 208When a substituent is attached to it, it is preferable that the substituent is not bulky, and R as a substituent 201 ~R 208 The substituent bonded to is preferably not an alkyl group or a cycloalkyl group, but rather an alkyl group, a cycloalkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, or -Si(R 901 )(R 902 )(R 903 A group represented by -O-(R 904 A group represented by -S-(R 905 A group represented by -N(R 906 )(R 907 A group represented by ), an aralkyl group, -C(=O)R 801 The base represented by -COOR 802 It is more preferable that the group is not a halogen atom, a cyano group, or a nitro group.

[0368] In the second compound, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0369] (Method for producing the second compound) The second compound can be produced by known methods. Alternatively, the second compound can also be produced by following known methods and using known alternative reactions and starting materials tailored to the target product.

[0370] (Specific examples of the second compound) Specific examples of the second compound include, for example, the following compounds. However, the present invention is not limited to these specific examples of the second compound.

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[0400] (Luminescent compound) In the organic EL element according to this embodiment, the luminescent compounds, such as the first luminescent compound and the second luminescent compound, are not particularly limited, but it is preferable that they be, for example, one or more compounds independently selected from the group consisting of a compound represented by the following general formula (4), a compound represented by the following general formula (5), and a compound represented by the following general formula (6).

[0401] (Compounds represented by general formula (4)) This section describes compounds represented by general formula (4).

[0402] [ka]

[0403] (In the above general formula (4), Z is independently either a CRa or a nitrogen atom. Rings A1 and A2 are independent of each other. 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. If there are multiple Ras, then one or more pairs of adjacent Ras 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, n21 and n22 are independently 0, 1, 2, 3, or 4. If there are multiple Rb groups, then one or more pairs of adjacent Rb groups 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, If there are multiple Rc, then one or more pairs of adjacent Rc elements 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, Rb, and Rc, which do not form the aforementioned substituted or unsubstituted monorings and do not form the aforementioned substituted or unsubstituted fused rings, are each 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, -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(R906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0404] (Specific examples of compounds represented by general formula (4)) Examples of compounds represented by the general formula (4) include the following compounds. In the examples below, Ph represents a phenyl group and D represents a deuterium atom.

[0405] [ka]

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[0415] (Compound represented by general formula (5)) This section describes compounds represented by general formula (5).

[0416] [ka]

[0417] (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 521 , R 522 , and R that does not form the substituted or unsubstituted monoring and does not form the 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 having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0418] (Specific examples of compounds represented by general formula (5)) Examples of compounds represented by the general formula (5) include the following compounds.

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[0435] (Compounds represented by general formula (6)) This section describes compounds represented by general formula (6).

[0436] [ka]

[0437] (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 R 602 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 having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0438] (Specific examples of compounds represented by general formula (6)) The following are specific examples of compounds represented by the general formula (6), but these are merely examples, and the compounds represented by the general formula (6) are not limited to the following examples.

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[0453] Among the luminescent compounds such as the first luminescent compound and the second luminescent compound, 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 having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon 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 from one another.

[0454] (Other layers of the organic EL element) The organic EL element according to this embodiment may have one or more organic layers in addition to the first light-emitting layer and the second light-emitting layer. Examples of organic layers include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron barrier layer, another hole barrier layer, an electron injection layer, and an electron transport layer.

[0455] In the organic EL element according to this embodiment, the element may consist only of a first light-emitting layer and a second light-emitting layer, but it 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 barrier layer, another hole barrier layer, an electron injection layer, and an electron transport layer.

[0456] Figure 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is constructed by stacking a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, an electron transport layer 8, and an electron injection layer 9 in that order, starting from the anode 3 side. The light-emitting band 5 of the organic EL element 1 consists of one first light-emitting layer 51.

[0457] Figure 2 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1A includes a light-transmitting 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 is constructed by stacking a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 51, a second light-emitting layer 52, an electron transport layer 8, and an electron injection layer 9 in that order, starting from the anode 3 side. The light-emitting band 5A of the organic EL element 1A includes the first light-emitting layer 51 on the anode 3 side and the second light-emitting layer 52 on the cathode 4 side.

[0458] Figure 3 shows a schematic configuration of another example of an organic EL element according to this embodiment. The organic EL element 1B includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10B disposed between the anode 3 and the cathode 4. The organic layer 10B is constructed by stacking a hole injection layer 6, a hole transport layer 7, a second light-emitting layer 52, a first light-emitting layer 51, an electron transport layer 8, and an electron injection layer 9 in that order, starting from the anode 3 side. The light-emitting band 5B of the organic EL element 1B includes the second light-emitting layer 52 on the anode 3 side and the first light-emitting layer 51 on the cathode 4 side.

[0459] The present invention is not limited to the configuration of the organic EL element shown in Figures 1, 2, and 3.

[0460] The configuration of the organic EL element will be explained further below. In the following text, symbols may be omitted.

[0461] In the organic EL element according to this embodiment, an organic layer may be disposed between the first light-emitting layer and the second light-emitting layer.

[0462] (intervening layer) The organic EL element according to this embodiment may also have an intervening layer as the organic layer disposed between the first light-emitting layer and the second light-emitting layer. In this embodiment, in order to prevent the Singlet emission region and the TTF emission region from overlapping, the intervening layer does not contain luminescent compounds to the extent that this can be achieved. For example, the content of the luminescent compound in the interlayer is not limited to 0% by mass. In cases where the luminescent compound is a component unintentionally introduced during the manufacturing process or a component present as an impurity in the raw material, the interlayer is permitted to contain these components. For example, if all the materials constituting the intervening layer are material A, material B, and material C, then the content of each of material A, material B, and material C in the intervening layer is 10% by mass or more, and the total content of material A, material B, and material C is 100% by mass. In the following, the intercalated layer may be referred to as the "undoped layer." The layer containing the luminescent compound may be referred to as the "doped layer."

[0463] Generally, when the light-emitting layer is constructed in a stacked configuration, the singlet light-emitting region and the TTF light-emitting region are more easily separated, which is said to improve luminous efficiency. In the organic EL element of this embodiment, when an intervening layer (undoped layer) is placed between the first light-emitting layer and the second light-emitting layer in the light-emitting band, the overlapping region between the singlet light-emitting region and the TTF light-emitting region is reduced, and it is expected that the decrease in TTF efficiency caused by collisions between triplet excitons and carriers will be suppressed. In other words, the insertion of an intervening layer (undoped layer) between light-emitting layers is considered to contribute to improving the efficiency of TTF emission.

[0464] The intervening layer is an undoped layer. The intercalated layer does not contain metal atoms. Therefore, the intercalated layer does not contain metal complexes. The intervening layer contains an intervening layer material. The intervening layer material is not a luminescent compound. The intervening layer material is not particularly limited, as long as it is 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.

[0465] The intervening layer material may be one or both of the first and second host materials, but is not particularly limited as long as it does not separate the Singlet emission region and the TTF emission region and does not hinder Singlet emission and TTF emission.

[0466] In the organic EL element according to this embodiment, the intervening layer is such that the content of each of the materials constituting the intervening layer is 10% by mass or more. The intervening layer includes the intervening layer material as a material constituting the intervening layer. 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.

[0467] The intervening layer may consist of a single layer or of two or more layers stacked together.

[0468] The thickness of the intervening layer is not particularly limited as long as it can suppress the overlap between the Singlet emission region and the TTF emission region, but it is preferably 3 nm to 15 nm per layer, and more preferably 5 nm to 10 nm. If the thickness of the intervening layer is 3 nm or more, it becomes easier to separate the singlet emission region from the emission region derived from the TTF. If the thickness of the intervening layer is 15 nm or less, it becomes easier to suppress the phenomenon of the host material in the intervening layer emitting light.

[0469] The intervening layer includes an intervening layer material as a constituent material of the intervening layer, and comprises the triplet energy T1(H1) of the first host material, the triplet energy T1(H2) of the second host material, and the triplet energy T1(M) of at least one intervening layer material. mid It is preferable that ) satisfies the relationship shown in the following formula (Equation 21). T1(H1) ≥ T1(M mid )≧T1(H2) …(Math 21)

[0470] If the intervening layer contains two or more intervening layer materials as materials constituting the intervening layer, the triplet energy T1(H1) of the first host material, the triplet energy T1(H2) of the second host material, and the triplet energy T1(M) of each intervening layer material are... EA It is more preferable that ) and satisfy the relationship shown in the following formula (Equation 21A). T1(H1) ≥ T1(M EA )≧T1(H2) …(Math 21A)

[0471] (substrate) The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), such as a plastic substrate. Examples of materials for forming a plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic vapor-deposited film may also be used.

[0472] (anode) For the anode 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).

[0473] 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.

[0474] 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.

[0475] 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.

[0476] (cathode) For the cathode, 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), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0477] 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.

[0478] 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.

[0479] (Hole injection layer) The hole injection layer is a layer containing a material with high hole injection properties. Suitable 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.

[0480] 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).

[0481] 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.

[0482] (Hole transport layer) The hole transport layer is a layer containing a material with high hole transport properties. In the organic EL element according to this embodiment, it is preferable that the hole transport layer contains a third compound. In the organic EL element according to this embodiment, it is preferable that a hole transport layer is arranged between the anode and the light-emitting band.

[0483] In the organic EL element according to this embodiment, the hole transport layer preferably contains a third compound represented by the following general formula (H1) or the following general formula (H2).

[0484] [ka]

[0485] (In the above general formula (H1), L 31 , L 32 and L 33 Each of them operates independently. Single bond, or A substituted or unsubstituted ring-forming arylene group with 6 to 18 carbon atoms, Ar 31 Ar 32 and Ar33 Each of them operates independently. Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, or -Si(R C1 )(R C2 )(R C3 It is a base represented by ), R C1、 R C2 and R C3 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms. R C1 If multiple R C1 They are either identical or different from one another. R C2 If multiple R C2 They are either identical or different from one another. R C3 If multiple R C3 They are either identical or different to one another.

[0486] [ka]

[0487] (In the above general formula (H2), A 41 and A 42 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or These are heterocyclic groups with 5 to 30 substituted or unsubstituted ring-forming atoms. R 410 ~R 414 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 420 ~R 424Of 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 410 ~R 414 R 420 ~R 424 Each of them operates independently. hydrogen atom, Cyano 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 ) halogen atom, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. m1 is 3, and there are three R 410 They are either identical or different from one another. m2 is 3, and there are 3 R 420 They are either identical or different from one another. L 41 and L 42 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or It is a divalent heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms.

[0488] (In the third compound represented by the general formula (H2), R 901 , R 902 , R 903 and R 904 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 having 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 to one another.

[0489] In the organic EL element according to this embodiment, the hole transport layer may also preferably contain a compound represented by the following general formula (H3) as a third compound.

[0490] [ka]

[0491] (In the above general formula (H3), L 34 , L 35 , L 36 and L 37 Each of them operates independently. Single bond, or A substituted or unsubstituted ring-forming arylene group with 6 to 18 carbon atoms, n2 is 1, 2, 3, or 4. If n2 is 1, L 38 These are substituted or unsubstituted ring-forming arylene groups with 6 to 18 carbon atoms. If n2 is 2, 3, or 4, then multiple L 38 They are either identical or different from each other. If n2 is 2, 3, or 4, then multiple L 38 teeth, They combine with each other to form a substituted or unsubstituted monoring, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, L that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 38 These are substituted or unsubstituted ring-forming arylene groups with 6 to 18 carbon atoms. Ar 34 Ar 35 Ar 36 and Ar 37 Each of them operates independently. Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, or -Si(R C1 )(R C2 )(R C3 It is a base represented by ), R C1、 R C2 and R C3 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms. R C1 If multiple R C1 They are either identical or different from one another. R C2 If multiple R C2 They are either identical or different from one another. R C3 If multiple R C3 They are either identical or different to one another.

[0492] In the organic EL element according to this embodiment, the third compound Ar 31Ar 32 and Ar 33 It is also preferable that at least one of these is a group represented by the following general formula (H11). In the organic EL element according to this embodiment, the third compound Ar 34 Ar 35 Ar 36 and Ar 37 It is also preferable that at least one of these is a group represented by the following general formula (H11).

[0493] [ka]

[0494] (In the above general formula (H11), X3 consists of an oxygen atom, a sulfur atom, and NR 319 or C(R 320 )(R 321 ) and R 311 ~R 318 A set consisting of two or more adjacent items is 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 320 and R 321 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 311 ~R 321 One of them is a single bond that connects to *e, or R 311 ~R 318 The carbon atoms constituting the ring skeleton of the substituted or unsubstituted monoring or substituted or unsubstituted fused ring, which are formed by the bonding of two or more adjacent pairs of carbon atoms, are bonded to *a by a single bond, or R 320 and R 321The carbon atoms constituting the ring skeleton of the substituted or unsubstituted monoring or substituted or unsubstituted fused ring formed by the bonding of sets of the above are bonded to *a by a single bond, R does not form the aforementioned substituted or unsubstituted monoring or substituted or unsubstituted fused ring, and is not a single bond attached to *a. 311 ~R 318 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 6 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or A heterocyclic group having 5 to 10 substituted or unsubstituted ring-forming atoms, *a is not a single bond R 319 teeth, hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, *a is not a single bond, and does not form the substituted or unsubstituted monoring, and does not form the substituted or unsubstituted fused ring. 320 and R 321 Each of them operates independently. hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, **Each of them is independent of L 31 , L 32 Or L 33 Is it a bonding position with L? 34 , L 35 , L 36 Or L 37 (It is either a bonding position with the nucleotide, or a bonding position with the nitrogen atom of the amino group.)

[0495] In at least one group represented by the general formula (H11) of the third compound, R 311 ~R 318It is also preferable that at least one of the pairs of adjacent rings, consisting of two or more rings, combine with each other to form a substituted or unsubstituted monoring, or a substituted or unsubstituted fused ring.

[0496] In at least one group represented by the general formula (H11) of the third compound, R 311 ~R 318 It is also preferable that at least one of the pairs of adjacent elements combine to form a substituted or unsubstituted benzene ring.

[0497] In at least one group represented by the general formula (H11) of the third compound, R 311 ~R 318 It is also preferable that one or two sets of two or more adjacent elements combine to form a substituted or unsubstituted benzene ring.

[0498] In at least one group represented by the general formula (H11) of the third compound, R 311 ~R 318 It is also preferable that any set of two or more adjacent elements does not combine with any other element.

[0499] In the organic EL element according to this embodiment, the third compound is A monoamine compound having one substituted or unsubstituted amino group in the molecule. Diamine compounds having two substituted or unsubstituted amino groups in the molecule, Triamine compounds having three substituted or unsubstituted amino groups in the molecule, and It is also preferable that the compound is at least one amine compound selected from the group consisting of tetraamine compounds having four substituted or unsubstituted amino groups in the molecule.

[0500] In the compounds represented by the general formula (H1) and the compounds represented by the general formula (H3), the substituents in the case of "substituted or unsubstituted" are -N(R C6 )(R C7 It is also preferable that the group is not represented by -N(RC6 )(R C7 In the group represented by ), R C6 and R C7 Each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group.

[0501] In the organic EL element according to this embodiment, the third compound is preferably at least one amine compound selected from the group consisting of monoamine compounds and diamine compounds.

[0502] In the organic EL element according to this embodiment, the third compound is also preferably a monoamine compound.

[0503] In the organic EL element according to this embodiment, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used for the hole transport layer. 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.

[0504] The hole transport layer 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.

[0505] 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.

[0506] (Specific examples of the third compound) Specific examples of the third compound include, for example, the following compounds. However, the present invention is not limited to these specific examples of the third compound.

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[0528] (Electron barrier layer) The electron barrier layer is preferably a layer that transports holes and prevents electrons from reaching the anode-side layer (e.g., the hole transport layer). The compound contained in the electron barrier layer is, for example, a compound used in known electron barrier layers, and is preferably at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. The compound contained in the electron barrier layer may also be a monoamine compound having only one substituted or unsubstituted amino group in its molecule. The compound contained in the electron barrier layer may also be a compound having a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in its molecule. The electron barrier layer may be a layer that prevents excitons generated in the light-emitting layer from moving to layers on the anode side of the electron barrier layer (for example, hole transport layers and hole injection layers) so that excitation energy does not leak from the light-emitting layer to the surrounding layers.

[0529] (Hole barrier layer) The hole barrier layer is preferably a layer that transports electrons and prevents holes from reaching the cathode-side layer (e.g., the electron transport layer). The compound contained in the hole barrier layer is, for example, a compound used in known hole barrier layers. The compound contained in the hole barrier layer is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described later. Alternatively, the compound contained in the hole barrier layer may be at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. The hole barrier layer is also preferably a layer that prevents excitons generated in the light-emitting layer from moving to layers on the cathode side of the hole barrier layer (e.g., electron transport layer and electron injection layer) so that excitation energy does not leak from the light-emitting layer to the surrounding layers.

[0530] (electron transport layer) The electron transport layer is a layer containing a material with high electron transport properties. In the organic EL element according to this embodiment, it is preferable that the electron transport layer contains a fourth compound. In the organic EL element according to this embodiment, it is preferable that an electron transport layer is arranged between the light-emitting band and the cathode.

[0531] In the organic EL element according to this embodiment, the electron transport layer preferably contains a fourth compound represented by the following general formula (E1).

[0532] [ka]

[0533] (In the above general formula (E1), X 51 , X 52 and X 53 Each of these is independently a nitrogen atom or CR5, However, X 51 , X52 and X 53 One or more of them are nitrogen atoms, R5 is hydrogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 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 ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Ax is A substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, or These are heterocyclic groups with 5 to 13 substituted or unsubstituted ring-forming atoms. Bx is A substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, or These are heterocyclic groups with 5 to 13 substituted or unsubstituted ring-forming atoms. L5 is single bond, Substituted or unsubstituted ring-forming aromatic hydrocarbon ring groups with 6 to 18 carbon atoms and (n+1) valency, A heterocyclic group with substituted or unsubstituted ring-forming atoms numbering 5 to 13 and having an (n+1) valency, or A (n+1) valence group formed by the bonding of two or three elements selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon ring groups having 6 to 18 ring-forming carbon atoms and substituted or unsubstituted heterocyclic ring groups having 5 to 13 ring-forming atoms. n is 1, 2, or 3, and if n is 2 or 3, L5 is not a single bond. Each Cx operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or These are heterocyclic groups with 5 to 60 substituted or unsubstituted ring-forming atoms. If multiple Cx exist, they may be identical or different from one another.

[0534] (In the fourth compound, R 901 , R 902 , R 903 and R 904 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 having 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 to one another.

[0535] In the organic EL element according to this embodiment, the fourth compound X 51 , X 52 and X 53 Preferably, two or three of these atoms are nitrogen atoms.

[0536] In the organic EL element according to this embodiment, the fourth compound is preferably a compound represented by the following general formulas (E11), (E12), (E13), or (E14).

[0537] [ka]

[0538] (In the above general formulas (E11) to (E14), Ax, Bx, Cx, R5, L5, and n are as defined in the above general formula (E1), respectively.)

[0539] In the organic EL element according to this embodiment, the substituent in the case of "substituted or unsubstituted" is preferably a group selected from the group consisting of alkyl groups having 1 to 50 carbon atoms, aryl groups having 6 to 50 ring-forming carbon atoms, and heterocyclic groups having 5 to 50 ring-forming atoms.

[0540] In the organic EL element according to this embodiment, the substituent in the phrase "substituted or unsubstituted" is preferably a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, aryl groups having 6 to 18 ring-forming carbon atoms, and heterocyclic groups having 5 to 18 ring-forming atoms.

[0541] In the organic EL element according to this embodiment, the electron transport layer can be made of: 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.

[0542] Furthermore, polymer compounds can also be used in the electron transport layer. 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.

[0543] (Specific examples of the fourth compound) Specific examples of the fourth compound include, for example, the following compounds. However, the present invention is not limited to these specific examples of the fourth compound.

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[0560] (electron injection layer) An electron injection layer is a layer containing a material with high electron injection potential. In the organic EL element according to this embodiment, the electron injection layer can be made of 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), or lithium oxide (LiOx). Alternatively, a substance 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.

[0561] Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used in the electron injection layer. 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 at 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.

[0562] (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.

[0563] (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.

[0564] (Emission wavelength of organic EL elements) In this embodiment, the organic electroluminescent element preferably emits light with a maximum peak wavelength of 500 nm or less when the element is driven. In this embodiment, it is more preferable that the organic electroluminescent element emits light with a maximum peak wavelength of 430 nm to 480 nm when the element is driven. The maximum peak wavelength of light emitted by the organic EL element during element operation 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) 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).

[0565] [Fourth Embodiment] (electronic equipment) The electronic device according to this embodiment is equipped with an organic EL element according to any of the embodiments described above. 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.

[0566] [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.

[0567] For example, the number of light-emitting layers in an organic EL element is not limited to one or two layers, but may consist of three or more stacked light-emitting layers. If an organic EL element has two or more light-emitting layers, it is sufficient that at least one light-emitting layer (the first light-emitting layer) satisfies 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.

[0568] 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.

[0569] 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]

[0570] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.

[0571] <Compound> The structures of the compounds represented by general formula (1) used in the manufacture of organic EL elements in Examples 1 to 4 are shown below.

[0572] [ka]

[0573] The structures of the comparative compounds used in the manufacture of the organic EL elements related to Comparative Examples 1 to 3 are shown below.

[0574] [ka]

[0575] The structures of other compounds used in the production of organic EL elements in Examples 1-4 and Comparative Examples 1-3 are shown below.

[0576] [ka]

[0577] <Fabrication of Organic EL Devices> Organic EL elements were fabricated and evaluated as follows.

[0578] (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 HT and compound HA were co-deposited onto the surface on which the transparent electrode lines were formed, covering the transparent electrodes, to form a hole injection layer with a thickness of 10 nm. The proportion of compound HT in this hole injection layer was set to 90% by mass, and the proportion of compound HA was set to 10% by mass. Next, compound HT was deposited on this hole injection layer to form a first hole transport layer with a thickness of 85 nm. Next, compound EBL was deposited on this first hole transport layer to form a second hole transport layer (sometimes referred to as an electron barrier layer) with a thickness of 5 nm. Next, compound BH1-1 (first host material) and compound BD (first luminescent compound) were co-deposited onto this second hole transport layer to form a first luminescent layer with a thickness of 5 nm. The proportion of compound BH1-1 in the first luminescent layer was set to 98% by mass, and the proportion of compound BD was set to 2% by mass. Next, compound BH2 (second host material) and compound BD (second luminescent compound) were co-deposited onto the first luminescent layer to form a second luminescent layer with a thickness of 15 nm. The proportion of compound BH2 in the second luminescent layer was set to 98% by mass, and the proportion of compound BD was set to 2% by mass. Next, a compound HBL was deposited on the second light-emitting layer to form a first electron transport layer (sometimes referred to as a hole barrier layer) with a thickness of 5 nm. Next, compound ET and compound Liq were co-deposited onto the first electron transport layer to form a second electron transport layer with a thickness of 25 nm. The proportion of compound ET in the second electron transport layer was set to 50% by mass, and the proportion of compound Liq was set to 50% by mass. Liq is an abbreviation for (8-Quinolinolato)lithium. Next, a Liq compound was deposited onto the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Next, metallic aluminum was deposited onto the electron injection layer to form a cathode with a thickness of 80 nm. The element configuration of Example 1 is schematically shown below. ITO(130) / HT:HA(10,90:10%) / HT(85) / EBL(5) / BH1-1:BD(5,98%:2%) / BH2:BD(15,98%:2%) / HBL(5) / ET:Liq(25,50%:50%) / Liq(1) / Al(80) In the simplified device configurations shown, the numbers in parentheses indicate the film thickness (in nm). Similarly, within the parentheses, the percentages (90%:10%) indicate the proportion (mass%) of compound HT and compound HA in the hole injection layer, the percentages (98%:2%) indicate the proportion (mass%) of the host material (compound BH1-1 or BH2) and luminescent compound (compound BD) in the first or second light-emitting layer, and the percentages (50%:50%) indicate the proportion (mass%) of compound ET and compound Liq in the second electron transport layer. The same notation will be used hereafter.

[0579] (Examples 2-4) The organic EL elements of Examples 2 to 4 were fabricated in the same manner as the organic EL element of Example 1, except that the compound BH1-1 used as the first host material for forming the first light-emitting layer was changed to one of the compounds shown in Table 1.

[0580] (Comparative Examples 1-3) The organic EL elements of Comparative Examples 1 to 3 were fabricated in the same manner as the organic EL element of Example 1, except that the compound BH1-1 used as the first host material for forming the first light-emitting layer was changed to one of the compounds shown in Table 1.

[0581] <Evaluation of Organic EL Devices> The fabricated organic EL elements were evaluated as follows. The evaluation results are shown in Table 1. Table 1 also shows the singlet energy S1 and triplet energy T1 of the compounds used in the light-emitting layer of each example.

[0582] (CIE1931 chromaticity) Current density is 10 mA / cm² 2 The CIE1931 chromaticity coordinates (x, y) were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the organic EL element in such a manner. Table 1 shows the CIEy values.

[0583] (Drive voltage) Current density is 10 mA / cm² 2 The voltage (in volts) was measured when current was passed between the anode and cathode of the organic EL element to achieve the desired result.

[0584] (External quantum efficiency EQE) Current density is 10 mA / cm² 2 The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to an organic EL element in such a manner. From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that lambassian emission occurred.

[0585] (Life span LT95) The fabricated 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 as the lifespan. Brightness was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0586] [Table 1]

[0587] In the organic EL elements of Examples 1 to 4, a compound represented by general formula (1) was used as the host material. As a result, the organic EL elements of Examples 1 to 4 had a longer lifetime LT95 compared to the organic EL elements of Comparative Examples 1 and 2. The organic EL elements of Examples 1, 2, and 4 also had a longer lifetime LT95 compared to the organic EL element of Comparative Example 3. The organic EL element of Example 3 maintained a similar level of chromaticity to that of Comparative Examples 1 and 2 while extending its lifetime. In all of Examples 1-4, the CIEy was less than 0.091, thus suppressing the deterioration of chromaticity compared to Comparative Example 3, which used a compound in which aryl groups were bonded to different rings of naphthobenzofuran.

[0588] <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 obtain a solution, which was then placed in a quartz cell to be used as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample was measured at a low temperature (77 [K]), and a tangent line was drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum. The wavelength value λ at the intersection of this tangent line and the horizontal axis was measured. edge Based on [nm], the energy amount calculated from the following conversion formula (F1) was defined as the triplet energy T1. 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 / λ edge

[0589] 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.

[0590] (Singlet energy S1) A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) was measured at room temperature (300 K). A tangent line was drawn to the falling edge on the long-wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis was substituted into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge A Hitachi spectrophotometer (model name: U3310) was used for measuring absorption spectra.

[0591] 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.

[0592] (Measurement of the maximum fluorescence emission peak wavelength (FL-peak)) The compound to be measured is 4.9 × 10 -6 A toluene solution was prepared by dissolving the substance in toluene at a concentration of mol / L. The peak fluorescence wavelength λ (in nm) when the toluene solution was excited at 390 nm was measured using a fluorescence spectrum analyzer (Spectrofluorometer F-7000 (manufactured by Hitachi High-Tech Science Corporation)). The peak fluorescence wavelength λ of compound BD was 455 nm.

[0593] <Example of synthesis> (Synthesis Example 1: Synthesis of BH1-1) Compound BH1-1 was synthesized according to the following synthesis scheme.

[0594] [ka]

[0595] (1) Synthesis of 10-bromonafto[1,2-b]benzofuran-7-ol (intermediate M1) [(10-bromonaphtho[1,2-b]benzofuran-7-yl)oxy]triisopropylsilane (2.26 g), cesium fluoride (1.80 g), and tetrahydrofuran (50 mL) were placed in a flask and stirred at room temperature for 5 hours. After the reaction was complete, the solution was cooled on ice and neutralized with 0.2 mol / L hydrochloric acid. Water was added to the solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and the slurry was filtered. The solid was washed with dichloromethane to obtain a white solid of 10-bromonaphtho[1,2-b]benzofuran-7-ol (1.47 g, yield 98%).

[0596] (2) Synthesis of 10-bromonafto[1,2-b]benzofuran-7-yl trifluoromethanesulfonate (intermediate M2) 10-Bromonaphtho[1,2-b]benzofuran-7-ol (intermediate M1) (1.47 g) and dichloromethane (40 mL) were placed in a flask and, under ice cooling, N,N-dimethyl-4-aminopyridine (0.58 g) and pyridine (0.40 mL) were added, followed by the dropwise addition of trifluoromethanesulfonic anhydride (1.30 mL), and the mixture was stirred for 4 hours while increasing the temperature to room temperature. After the reaction was complete, saturated sodium bicarbonate solution was added to the solution under ice cooling. The solution was extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and the residue was purified by silica gel column chromatography to obtain a white solid (1.50 g, yield 72%) of 10-bromonaphtho[1,2-b]benzofuran-7-yl trifluoromethanesulfonate.

[0597] (3) Synthesis of 7,10-di(pyrene-1-yl)naphtho[1,2-b]benzofuran (compound BH1-1) 10-bromonafto[1,2-b]benzofuran-7-yl trifluoromethanesulfonate (intermediate M2) (1.0 g), pyrene-1-ylboronic acid (1.2 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (0.20 g), sodium carbonate (0.50 g), 1,4-dioxane (20 mL), and deionized water (2 mL) were added to a flask and heated under reflux and stirred under an argon atmosphere for 18 hours. After the reaction was complete, the solution was allowed to cool to room temperature and a sufficient amount of water was added. The solid was filtered and washed with methanol. The solid was heated and dissolved in toluene and passed through a silica gel short column. The solvent was removed by distillation to obtain the solid. The obtained solid was recrystallized in toluene to yield a pale yellow solid of 7,10-di(pyrene-1-yl)naphtho[1,2-b]benzofuran (compound BH1-1) (406 mg, yield 29%). Mass spectral analysis revealed a molecular weight of 618.74 and a m / e ratio of 619, identifying it as the target compound.

[0598] (Synthesis Example 2: Synthesis of BH1-2) Compound BH1-2 was synthesized according to the following synthesis scheme.

[0599] [ka]

[0600] (1) Synthesis of 4-bromonafto[2,3-b]benzofuran-1-ol (intermediate M3) [(4-bromonaphtho[2,3-b]benzofuran-1-yl)oxy]triisopropylsilane (5.00 g), cesium fluoride (4.00 g), and tetrahydrofuran (100 mL) were placed in a flask and stirred at room temperature for 5 hours. After the reaction was complete, the solution was cooled on ice and neutralized with 0.2 mol / L hydrochloric acid. Water was added to the solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and the slurry was filtered. The solid was washed with dichloromethane to obtain a white solid of 4-bromonaphtho[2,3-b]benzofuran-1-ol (3.20 g, yield 96%).

[0601] (2) Synthesis of 4-bromonafto[2,3-b]benzofuran-1-yl trifluoromethanesulfonate (intermediate M4) 4-bromonaphtho[2,3-b]benzofuran-1-ol (intermediate M3) (3.1 g) and dichloromethane (100 mL) were placed in a flask and, under ice cooling, N,N-dimethyl-4-aminopyridine (1.21 g) and pyridine (1.6 mL) were added, followed by the dropwise addition of trifluoromethanesulfonic anhydride (2.0 mL), and the mixture was stirred for 4 hours while increasing the temperature to room temperature. After the reaction was complete, saturated sodium bicarbonate solution was added to the solution under ice cooling. The solution was extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and the residue was purified by silica gel column chromatography to obtain a white solid of 4-bromonaphtho[2,3-b]benzofuran-1-yl trifluoromethanesulfonate (3.57 g, yield 81%).

[0602] (3) Synthesis of 1,4-di(pyrene-1-yl)naphtho[2,3-b]benzofuran (compound BH1-2) 4-bromonaphtho[2,3-b]benzofuran-1-yl trifluoromethanesulfonate (intermediate M4) (1.70 g), pyrene-1-ylboronic acid (1.97 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.10 g), tris(dibenzylideneacetone)dipalladium (0) (54 mg), tripotassium phosphate (1.62 g), and 1,4-dioxane (80 mL) were added to a flask and heated under reflux and stirred under an argon atmosphere for 6 hours. After the reaction was complete, the solution was allowed to cool to room temperature and a sufficient amount of water was added. The solid was filtered and washed with methanol. The solid was heated and dissolved in toluene and passed through a silica gel short column. The solvent was removed by distillation to obtain the solid. The obtained solid was recrystallized in toluene to yield a pale yellow solid (945 mg, 40% yield) of 1,4-di(pyrene-1-yl)naphtho[2,3-b]benzofuran (compound BH1-2). Mass spectral analysis revealed a molecular weight of 618.74 and an m / e ratio of 619, identifying it as the target compound.

[0603] (Synthesis Example 3: Synthesis of BH1-3) Compound BH1-3 was synthesized according to the following synthesis scheme.

[0604] [ka]

[0605] (1) Synthesis of triisopropyl{[4-(benzo[a]anthracen-7-yl)naphtho[2,3-b]benzofuran-1-yl]oxysilane (intermediate M5) [(4-bromonaphtho[2,3-b]benzofuran-1-yl)oxy]triisopropylsilane (5.00 g), benzo[a]anthracene-7-ylboronic acid (4.35 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.30 g), tris(dibenzylideneacetone)dipalladium (0) (0.15 g), tripotassium phosphate (4.50 g), and 1,4-dioxane (120 mL) were added to a flask and heated under reflux and stirred under an argon atmosphere for 6 hours. After the reaction was complete, the solution was allowed to cool to room temperature and a sufficient amount of water was added. The solid was filtered and washed with methanol. The solid was heated and dissolved in toluene and passed through a silica gel short column. The solvent was removed by distillation to obtain the solid. The solution was purified by silica gel column chromatography to obtain a white solid of triisopropyl{[4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran-1-yl]oxysilane (4.65 g, yield 71%).

[0606] (2) Synthesis of 4-(benzo[a]anthracen-7-yl)naphtho[2,3-b]benzofuran-1-ol (intermediate M6) Triisopropyl{[4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran-1-yl]oxy}silane (intermediate M5) (4.60 g), cesium fluoride (2.83 g), and tetrahydrofuran (80 mL) were placed in a flask and stirred by flow at room temperature for 5 hours. After the reaction was complete, the solution was neutralized with 0.2 mol / L hydrochloric acid under ice cooling. Water was added to the solution and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and the slurry was filtered. The solid was washed with dichloromethane to obtain a white solid of 4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran-1-ol (2.92 g, yield 85%).

[0607] (3) Synthesis of 4-(benzo[a]anthracen-7-yl)naphtho[2,3-b]benzofuran-1-yl trifluoromethanesulfonate (intermediate M7) 4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran-1-ol (intermediate M6) (2.9 g) and dichloromethane (130 mL) were placed in a flask. Under ice cooling, N,N-dimethyl-4-aminopyridine (0.77 g) and pyridine (1.0 mL) were added, followed by dropwise addition of trifluoromethanesulfonic acid anhydride (1.3 mL). The mixture was stirred for 5 hours while gradually increasing the temperature to room temperature. After the reaction was complete, saturated sodium bicarbonate solution was added to the solution under ice cooling. The solution was extracted with dichloromethane, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and the residue was purified by silica gel column chromatography to obtain a white solid (3.30 g, yield 88%) of 4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran-1-yl trifluoromethanesulfonate.

[0608] (4) Synthesis of 1-(pyrene-1-yl)-4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran (compound BH1-3) 4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran-1-yl trifluoromethanesulfonate (intermediate M7) (1.70 g), pyrene-1-ylboronic acid (0.75 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (81 mg), tris(dibenzylideneacetone)dipalladium (0) (41 mg), tripotassium phosphate (0.91 g), and 1,4-dioxane (50 mL) were added to a flask and heated under reflux and stirred under an argon atmosphere for 6 hours. After the reaction was complete, the solution was allowed to cool to room temperature and a sufficient amount of water was added. The solid was filtered and washed with methanol. The solid was heated and dissolved in toluene and passed through a silica gel short column. The solvent was removed by distillation to obtain the solid. The obtained solid was recrystallized in toluene to yield a pale yellow solid (810 mg, 44% yield) of 1-(pyrene-1-yl)-4-(benzo[a]anthracene-7-yl)naphtho[2,3-b]benzofuran (compound BH1-3). Mass spectral analysis revealed a molecular weight of 644.77 and a m / e ratio of 645, identifying it as the target compound.

[0609] (Synthesis Example 4: Synthesis of BH1-4) Compound BH1-4 was synthesized according to the following synthesis scheme.

[0610] [ka]

[0611] (1) Synthesis of 1-fluoro-2-(2,4,6-trimethoxyphenyl)naphthalene (intermediate M8) 2-Bromo-1,3,5-trimethoxybenzene (5.00 g), (1-fluoronaphthalen-2-yl)boronic acid (4.61 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.57 g), tris(dibenzylideneacetone)dipalladium (0) (0.29 g), tripotassium phosphate (6.43 g), and 1,4-dioxane (200 mL) were added to a flask and heated under reflux and stirred under an argon atmosphere for 5 hours. After the reaction was complete, the solution was allowed to cool to room temperature and a sufficient amount of water was added. Dioxane was removed by distillation, and the solution was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography to obtain a white solid of 1-fluoro-2-(2,4,6-trimethoxyphenyl)naphthalene (5.90 g, yield 93%).

[0612] (2) Synthesis of 2-(1-fluoronaphthalene-2-yl)benzene-1,3,5-triol (intermediate M9) 1-Fluoro-2-(2,4,6-trimethoxyphenyl)naphthalene (intermediate M8) (4.90 g) and dichloromethane (150 mL) were added to a flask, cooled on ice under an argon atmosphere, and 1.0 mol / L boron tribromide dichloromethane solution (95 mL) was added dropwise, and the mixture was stirred at room temperature for 5 hours. After the reaction was complete, cold water was added dropwise to the solution under ice cooling, and it was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the solvent was removed by distillation, and the residue was purified by silica gel column chromatography to obtain a white solid of 2-(1-fluoronaphthalene-2-yl)benzene-1,3,5-triol (3.41 g, yield 80%).

[0613] (3) Synthesis of naphtho[1,2-b]benzofuran-7,9-diol (intermediate M10) 2.9 g of 2-(1-fluoronaphthalene-2-yl)benzene-1,3,5-triol (intermediate M9), 2.23 g of potassium carbonate, and 210 mL of N-methyl-2-pyrrolidone were added to a flask and heated and stirred at 150 °C under an argon atmosphere for 5 hours. After the reaction was complete, the reaction mixture was allowed to cool to room temperature, 500 mL of water was added, and the pH was adjusted to 3 with dilute hydrochloric acid. The precipitated solid was filtered off and purified by silica gel column chromatography to obtain a white solid of naphtho[1,2-b]benzofuran-7,9-diol (1.71 g, yield 64%).

[0614] (4) Synthesis of naphtho[1,2-b]benzofuran-7,9-diylbis(trifluoromethanesulfonate) (intermediate M11) Naphtho[1,2-b]benzofuran-7,9-diol (intermediate M10) (1.6 g) and dichloromethane (130 mL) were placed in a flask. Under ice cooling, N,N-dimethyl-4-aminopyridine (0.78 g) and pyridine (1.3 mL) were added, followed by the dropwise addition of trifluoromethanesulfonic acid anhydride (2.6 mL). The mixture was stirred for 5 hours while gradually increasing the temperature to room temperature. After the reaction was complete, saturated sodium bicarbonate solution was added to the solution under ice cooling. The solution was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The solvent was then removed by distillation, and the residue was purified by silica gel column chromatography to obtain a white solid of naphtho[1,2-b]benzofuran-7,9-diylbis(trifluoromethanesulfonate) (2.55 g, yield 78%).

[0615] (5) Synthesis of 7,9-di(pyrene-1-yl)naphtho[1,2-b]benzofuran (compound BH1-4) Naphtho[1,2-b]benzofuran-7,9-diylbis(trifluoromethanesulfonate) (intermediate M11) (1.20 g), pyrene-1-ylboronic acid (1.20 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (132 mg), tris(dibenzylideneacetone)dipalladium (0) (66 mg), tripotassium phosphate (1.24 g), and 1,4-dioxane (50 mL) were added to a flask and heated under reflux and stirred under an argon atmosphere for 6 hours. After the reaction was complete, the solution was allowed to cool to room temperature and a sufficient amount of water was added. The solid was filtered and washed with methanol. The solid was heated and dissolved in toluene and passed through a silica gel short column. The solvent was removed by distillation to obtain the solid. The obtained solid was recrystallized in toluene to yield a pale yellow solid (0.95 g, 66% yield) of 7,9-di(pyrene-1-yl)naphtho[1,2-b]benzofuran (compound BH1-4). Mass spectrometry revealed a molecular weight of 618.74 and a m / e ratio of 619, identifying it as the target compound. [Explanation of Symbols]

[0616] 1...Organic electroluminescent element, 1A...Organic electroluminescent element, 1B...Organic electroluminescent element, 10...Organic layer, 10A...Organic layer, 10B...Organic layer, 2...Substrate, 3...Anode, 4...Cathode, 5...Emission band, 5A...Emission band, 5B...Emission band, 51...First emission layer, 52...Second emission layer, 61...Hole injection layer, 62...Hole transport layer, 71...Electron transport layer, 72...Electron injection layer.

Claims

1. A compound represented by the following general formula (1). 【Chemical Formula 1】 (In the general formula (1), R １ ~R ９ 、R １０１ ~R １０８ and R １１１ ~R １１８ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 21 ring-forming atoms, Ar １２ is a substituted or unsubstituted aryl group having 10 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 9 to 31 ring-forming atoms, The substituted aryl group as Ar １２ has or does not have at least one group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 21 ring-forming atoms as a substituent, The substituted heterocyclic group as Ar １２ has or does not have at least one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 21 ring-forming atoms as a substituent, L １１ and L １２ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 10 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring-forming atoms, p is 0 or 1, q is 0 or 1, p + q is 1 or 2. However, when p is 1, R １０１ and R １０２ , R １０２ and R １０３ , or R １０３ and R １０４ is a single bond that binds to *a, and R １０１ and R １０２ , R １０２ and R １０３ , or R １０３ and R １０４ is a single bond that binds to *b, When q is 0, one of the two selected from R １０５ to R １０８ is a single bond that binds to *e, and the other is a single bond that binds to *f, When q is 1, one of the two selected from R １０５ and R １０６ , R １０６ and R １０７ , or R １０７ and R １０８ is a single bond that binds to *c, and R １０５ and R １０６ , R １０６ and R １０７ , or R １０７ and R １０８ is a single bond that binds to *d, and R that is not a single bond that binds to *c and *d １０５ to R １０８ , and R １１５ to R １１８ Among the two selected from, one is a single bond that binds to *e, and the other is a single bond that binds to *f.)

2. The compound represented by the general formula (1) is the one represented by the following general formula (10), The compound according to claim 1. 【Chemical formula 2】 (In the general formula (10), R １ to R ９ , R １０１ to R １０８ , R １１１ to R １１４ , Ar １２ , L １１ , L １２ , *a, *b, *e and *f are as defined in the general formula (1) respectively.)

3. The compound represented by the general formula (1) is represented by the following general formula (11), The compound according to claim 2. 【Chemical Formula 3】 (In the general formula (11), R １ ~R ９ 、R １０１ ~R １０７ 、R １１１ ~R １１４ 、Ar １２ 、L １１ 、L １２ 、*a, *b and *f are as defined in the general formula (1) respectively.)

4. In the compound represented by the general formula (1), R １０５ or R １０６ is a single bond connecting to *f, The compound according to claim 2.

5. In the compound represented by the general formula (1), one of R １０２ and R １０３ is a single bond connecting to *a, and the other of R １０２ and R １０３ is a single bond connecting to *b, The compound according to claim 1.

6. In the compound represented by the general formula (1), one of R １０３ and R １０４ is a single bond connecting to *a, and the other of R １０３ and R １０４ is a single bond connecting to *b, The compound according to claim 1.

7. In the compound represented by the general formula (1), Ar １２ is an aryl group with 4 or fewer monocyclic rings condensed, The compound according to claim 1.

8. In the compound represented by the general formula (1), R １ ~R ９ and R which is not a single bond １０１ to R １０８ and R which is not a single bond １１１ to R １１８ are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 10 ring-forming carbon atoms. The compound according to claim 1.

9. In the compound represented by the general formula (1), R １ to R ９ and R which is not a single bond １０１ to R １０８ and R which is not a single bond １１１ to R １１８ are hydrogen atoms. The compound according to claim 1.

10. In the compound represented by the general formula (1), the aryl group as Ar １２ has an aryl group having 6 to 10 ring-forming carbon atoms as a substituent. The compound according to claim 1.

11. In the compound represented by the general formula (1), Ar １２ is an unsubstituted aryl group having 10 to 30 ring-forming carbon atoms. The compound according to claim 1.

12. In the compound represented by the general formula (1), L １１ is a single bond. The compound according to claim 1.

13. An organic electroluminescence device comprising an anode, a cathode, and a light-emitting zone disposed between the anode and the cathode, and the light-emitting zone includes a first light-emitting layer containing the compound according to any one of claims 1 to 12 as a first host material. An organic electroluminescence device.

14. The emission band further includes a second light-emitting layer, The first light-emitting layer includes the first host material and a first light-emitting compound, The second light-emitting layer includes a second host material and a second light-emitting compound, The first host material and the second host material are different from each other, The first light-emitting compound and the second light-emitting compound are the same as or different from each other, The organic electroluminescence element according to claim 13.

15. The triplet energy T １ (H1) of the first host material and the triplet energy T １ (H2) of the second host material satisfy the following relational expression (Equation 1), The organic electroluminescence element according to claim 14. T １ (H1) > T １ (H2) … (Equation 1)

16. The first light-emitting compound and the second light-emitting compound are each independently a compound that exhibits light emission having a maximum peak wavelength of 500 nm or less, The organic electroluminescence element according to claim 14.

17. The first light-emitting layer is disposed between the anode and the second light-emitting layer, The organic electroluminescence element according to claim 14.

18. The second host material is a second compound represented by the following general formula (2), The organic electroluminescence element according to claim 14. 【Chemical Formula 4】 (In the general formula (2), R ２０１ ~R ２０８ are each independently, a hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ ) group represented by, -O-(R ９０４ ) group represented by, -S-(R ９０５ ) group represented by, -N(R ９０６ )(R ９０７ ) group represented by, A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ８０１ ) group represented by, -COOR ８０２ ) group represented by, A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L ２０１ and L ２０２ are each independently, A single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, Ar ２０１ and Ar ２０２ are each independently, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. ) (In the second host material, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ８０１ and R ８０２ are each independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R ９０１ When there are a plurality of R's, the plurality of R's ９０１ are the same as or different from each other, R ９０２ When there are a plurality of R's, the plurality of R's ９０２ are the same as or different from each other, R ９０３ When there are a plurality of R's, the plurality of R's ９０３ are the same as or different from each other, R ９０４ When there are a plurality of R's, the plurality of R's ９０４ are the same as or different from each other, R ９０５ When there are a plurality of R's, the plurality of R's ９０５ are the same as or different from each other, R ９０６ When there are a plurality of R's, the plurality of R's ９０６ are the same as or different from each other, R ９０７ When there are a plurality of R's, the plurality of R's ９０７ are the same as or different from each other, R ８０１ When there are a plurality of R's, the plurality of R's ８０１ are the same as or different from each other, R ８０２ When there are a plurality of R's, the plurality of R's ８０２ are the same as or different from each other.)

19. A hole transport layer is disposed between the anode and the light-emitting band. The hole transport layer contains a third compound represented by the following general formula (H1) or the following general formula (H2). The organic electroluminescence device according to claim 13. [Chemical Formula 5] (In the general formula (H1), L ３１ 、L ３２ and L ３３ are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, Ar ３１ 、Ar ３２ and Ar ３３ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, or a group represented by -Si(R Ｃ１ )(R Ｃ２ )(R Ｃ３ ), R Ｃ１、 R Ｃ２ and R Ｃ３ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, When there are a plurality of R Ｃ１ , the plurality of R Ｃ１ are the same as or different from each other, When there are a plurality of R Ｃ２ , the plurality of R Ｃ２ are the same as or different from each other, When there are a plurality of R Ｃ３ , the plurality of R Ｃ３ are the same as or different from each other.) [Chemical Formula 6] (In the general formula (H2), A ４１ and A ４２ are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, R ４１０ ~R ４１４ one or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R ４２０ ~R ４２４ one or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, R ４１０ ~R ４１４ as well as R ４２０ ~R ４２４ are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R ９０１ )(R ９０２ )(R ９０３ ) group represented by, -O-(R ９０４ ) group represented by, a halogen atom, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, m1 is 3, and the three Rs ４１０ are the same as or different from each other, m2 is 3, and the three Rs ４２０ are the same as or different from each other, L ４１ and L ４２ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms. ) (In the third compound represented by the general formula (H2), R ９０１ 、R ９０２ 、R ９０３ and R ９０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and when a plurality of Rs ９０１ are present, the plurality of Rs ９０１ are the same as or different from each other, when a plurality of Rs ９０２ are present, the plurality of Rs ９０２ are the same as or different from each other, when a plurality of Rs ９０３ are present, the plurality of Rs ９０３ are the same as or different from each other, when a plurality of Rs ９０４ are present, the plurality of Rs ９０４ are the same as or different from each other. )

20. An electron transport layer is disposed between the light emission band and the cathode, and the electron transport layer contains a fourth compound represented by the following general formula (E1). The organic electroluminescent device according to claim 13. 【Chemical Formula 7】 (In the general formula (E1), X ５１ , X ５２ and X ５３ are each independently a nitrogen atom or CR ５ , and however, among X ５１ , X ５２ and X ５３ , one or more are nitrogen atoms, R ５ is a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a group represented by -Si(R ９０１ )(R ９０２ )(R ９０３ ), a group represented by -O-(R ９０４ ), a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, Ax is a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms, Bx is a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms, L ５ is a single bond, a substituted or unsubstituted (n + 1)-valent aromatic hydrocarbon ring group having 6 to 18 ring-forming carbon atoms, a substituted or unsubstituted (n + 1)-valent heterocyclic group having 5 to 13 ring-forming atoms, or An (n + 1)-valent group formed by bonding two or three selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring-forming atoms, n is 1, 2, or 3; when n is 2 or 3, L ５ is not a single bond, Each Cx is independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring-forming atoms, When there are a plurality of Cx, the plurality of Cx may be the same as or different from each other.) (In the fourth compound, R ９０１ , R ９０２ , R ９０３ and R ９０４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, When there are a plurality of R ９０１ , the plurality of R ９０１ may be the same as or different from each other, When there are a plurality of R ９０２ , the plurality of R ９０２ may be the same as or different from each other, When there are a plurality of R ９０３ , the plurality of R ９０３ may be the same as or different from each other, When there are a plurality of R ９０４ , the plurality of R ９０４ may be the same as or different from each other.)

21. An electronic device equipped with the organic electroluminescence element according to claim 13.

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