Compounds, materials for organic electroluminescent elements, organic electroluminescent elements and electronic devices

Abstract

To provide novel compounds for use as host materials in organic electroluminescent devices. [Solution] A compound represented by formula (1). R1~R 12 At least one of them is a group represented by formula (11), and Ar is a group derived from the ring structure represented by formula (12). TIFF2026102992000263.tif73159

Description

[Technical Field]

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

[0002] When a voltage is applied to an organic electroluminescent device (hereinafter sometimes referred to as an "organic EL device"), 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%. Fluorescent organic light-emitting diodes (OLEDs), which use light emission from singlet excitons, are being applied to full-color displays in mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, research is being conducted to improve the performance of OLEDs.

[0003] For example, Patent Documents 1 to 7 describe studies on compounds that can be used in organic electroluminescent devices (for example, compounds in which a benzofuran ring is bonded to an anthracene ring). Furthermore, Patent Document 8 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 devices. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] U.S. Patent Application Publication No. 2022 / 0181559 [Patent Document 2] International Publication No. 2021 / 021840 [Patent Document 3] U.S. Patent Application Publication No. 2011 / 0101310

Patent Document 4

Patent Document 5

Patent Document 6

Patent Document 7

Patent Document 8

Summary of the Invention

Problems to be Solved by the Invention

[0005] In order to improve the performance of electronic devices such as displays, further improvement in the performance of organic EL elements is desired. Examples of the performance of organic EL elements include luminance, emission wavelength, full width at half maximum, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0006] An object of the present invention is to provide a novel compound that can be used as a host material for an organic electroluminescence element. Another object of the present invention is to provide a compound that can improve the performance of an organic electroluminescence element when used as a host material. Another object of the present invention is to provide a material for an organic electroluminescence element containing the compound. Another object of the present invention is to provide an organic electroluminescence element containing a compound capable of improving performance, and an electronic device equipped with the organic electroluminescence element.

Means for Solving the Problems

[0007] According to one aspect of the present invention, a compound represented by the following general formula (1) is provided.

[0008]

Chemical Formula

[0009] (In the general formula (1), R1 to R 12 are each independently a hydrogen atom, 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, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 801 ) group represented by, <​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​ n is 0, 1, 2, or 3. If there are two or more L1s, then the two or more L1s are either identical or different from each other. In the above general formula (12), R 23 ~R 27 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 bind to each other, Regarding the bond between the ring structure represented by the general formula (12) and L1, (i)R 23 ~R 27 If one or more adjacent pairs of atoms form a substituted or unsubstituted monoring, or if one of these pairs forms an atom that constitutes a monoring, then L1 is bonded to the atom, (ii)R 23 ~R 27 Either one or more adjacent pairs of atoms form a substituted or unsubstituted fused ring, and an atom from that ring bonds to L1, or (iii) R that does not form the substituted or unsubstituted monoring and the substituted or unsubstituted fused ring. 22 ~R 27 One of these is a single bond that connects to L1, R is not a single bond that connects to L1. 22 , and R that does not form the substituted or unsubstituted monoring, does not form the substituted or unsubstituted fused ring, and is not a single bond bonded to L1. 23 ~R 27 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(R901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 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. * indicates the bond position with the benzanthracene ring in the general formula (1) above. (In the compound represented by the general formula (1) above, R 901 , R 902 , R 903 , R 904 , R 905 , 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 904If 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 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.

[0010] According to one aspect of the present invention, a material for an organic electroluminescent device containing a compound according to one aspect of the present invention is provided.

[0011] According to one aspect of the present invention, an organic electroluminescent element is provided, comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer contains a compound according to one aspect of the present invention as a first host material.

[0012] 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]

[0013] According to one aspect of the present invention, a novel compound that can be used as a host material for an organic electroluminescent element can be provided. According to one aspect of the present invention, a compound that can improve the performance of an organic electroluminescent element when used as a host material can be provided. According to one aspect of the present invention, a material for an organic electroluminescent element containing the compound can be provided. According to one aspect of the present invention, an organic electroluminescent element containing a compound that can improve performance can be provided, as well as an electronic device equipped with the organic electroluminescent element can be provided. [Brief explanation of the drawing]

[0014] [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]

[0015] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0016] 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.

[0017] 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.

[0018] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

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

[0020] In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" means that "atom count XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more.

[0021] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0022] "Substituents as described herein" The substituents described herein will be explained below.

[0023] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

[0024] • "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.

[0025] • 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).

[0026] [ka]

[0027] [ka]

[0028] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.

[0029] • "Substitutable or unsubstituted heterocyclic groups" The “heterocyclic group” as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic group" as described herein is either a monocyclic group or a fused-cyclic group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B), etc. (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.

[0030] 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).

[0031] 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).

[0032] • 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.

[0033] • 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.

[0034] • 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).

[0035] • 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):

[0036] [ka]

[0037] [ka]

[0038] 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.

[0039] • 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.

[0040] • 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].

[0041] • 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].

[0042] • 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):

[0043] 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 A This refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms is CH2.

[0044] • "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.

[0045] • 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.

[0046] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0047] • "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.

[0048] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0049] • 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.

[0050] • "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.

[0051] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group.

[0052] • "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.

[0053] • 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.

[0054] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0055] · "-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.

[0056] ·「-O-(R 904 ) a base represented by The following information pertains to the -O-(R 904 ) 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.

[0057] · "-S-(R 905 ) a base represented by -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.

[0058] · "-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.

[0059] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0060] • "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.

[0061] • "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.

[0062] • "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.

[0063] • "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.

[0064] • "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.

[0065] • "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.

[0066] • "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.

[0067] • "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.

[0068] 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.

[0069] 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.

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

[0071] [ka]

[0072] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0073] [ka]

[0074] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0075] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:

[0076] [ka]

[0077] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0078] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0079] • "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.

[0080] • "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.

[0081] • "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.

[0082] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0083] [ka]

[0084] [ka]

[0085] 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.

[0086] [ka]

[0087] 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.

[0088] [ka]

[0089] 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.

[0090] 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).

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0100] The above is a description of the substituents described herein.

[0101] • "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.

[0102] [ka]

[0103] For example, R921 ~R 930 In the case of "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 is 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.

[0104] 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<00​​​​​​​​​​​​​​​​​​​​​​​923 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.

[0107] [ka]

[0108] 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.

[0109] 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 the 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.

[0110] 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.

[0111] 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").

[0112] • 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 These are groups selected from the group consisting of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, 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, It is 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 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. R 903 If there are two or more of them, then there are two or more R903 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.

[0113] 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 It is a group selected from the group consisting of heterocyclic groups with 5 to 50 ring-forming atoms.

[0114] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, A ring-forming aryl group with 6 to 18 carbon atoms, and It is a group selected from the group consisting of heterocyclic groups with 5 to 18 ring-forming atoms.

[0115] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] [First Embodiment] <Compound> The compound according to this embodiment is a compound represented by the following general formula (1).

[0120] [ka]

[0121] (In the above general formula (1), R1~R 12 Each of them operates independently. hydrogen atom, 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 905A 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 Cyano group, Nitro group, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (11) above, However, R1~R 12 At least one of them is a group represented by the general formula (11), If there are multiple groups represented by the general formula (11), the multiple groups represented by the general formula (11) may be identical or different from each other. In the above general formula (11), Ar is a group derived from the ring structure represented by the general formula (12) above, L1 is single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, n is 0, 1, 2, or 3. If there are two or more L1s, then the two or more L1s are either identical or different from each other. In the above general formula (12), R 23 ~R 27 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 bind to each other, Regarding the bond between the ring structure represented by the general formula (12) and L1, (i)R 23 ~R 27If one or more adjacent pairs of atoms form a substituted or unsubstituted monoring, or if one of these pairs forms an atom that constitutes a monoring, then L1 is bonded to the atom, (ii)R 23 ~R 27 Either one or more adjacent pairs of atoms form a substituted or unsubstituted fused ring, and an atom from that ring bonds to L1, or (iii) R that does not form the substituted or unsubstituted monoring and the substituted or unsubstituted fused ring. 22 ~R 27 One of these is a single bond that connects to L1, R is not a single bond that connects to L1. 22 , and R that does not form the substituted or unsubstituted monoring, does not form the substituted or unsubstituted fused ring, and is not a single bond bonded to L1. 23 ~R 27 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 ) 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. * indicates the bond position with the benzanthracene ring in the general formula (1) above. (In the compound represented by the general formula (1) above, R 901 , R 902 , R 903 , R 904 , R 905 , 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 801 If multiple R 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.

[0122] According to one embodiment of the compound described herein, a novel compound that can be used as a host material for an organic EL element can be provided. According to one embodiment of the compound of this embodiment, having the structure shown in general formula (1) (a structure in which a benzofuran ring is bonded to a benzanthracene ring via a single bond or a linking group) makes it possible to improve the performance of an organic EL element when used as a host material.

[0123] In the compound according to this embodiment, the bonding mode of (i) (the bonding mode between the ring structure represented by the general formula (12) and L1) will be explained using the following compound X1 as an example. Compound X1 is R in the general formula (12) above. 26 and R 27 The set of atoms is bonded to each other to form an unsubstituted monoring, and the atoms constituting this unsubstituted monoring (at the position of *1) are bonded to the naphthylene group as L1, giving it a structure. Furthermore, the bonding mode of (ii) above (the bonding mode between the ring structure represented by the general formula (12) and L1) will be explained using the following compound X2 as an example. Compound X2 is R in the general formula (12) above. 24 and R 25 The group, R 25 and R 26 The set, and R 26 and R 27 The set of atoms is bonded to each other to form an unsubstituted fused ring, and the atoms constituting the formed fused ring (at the position of *2) are bonded to the naphthylene group as L1, giving it a structure.

[0124] [ka]

[0125] In the general formula (11) above, when n is 0, (L1)n represents a single bond. In the compound according to this embodiment, when (L1)n is a single bond, the bonding mode of (i) (the bonding mode between the ring structure represented by the general formula (12) and L1) will be explained using the following compound X3 as an example. Compound X3 is R in the general formula (12) above. 26 and R 27The set of atoms is bonded to each other to form an unsubstituted monoring, and the atoms constituting the formed unsubstituted monoring (at position *1) are directly bonded to the atoms constituting the benzanthracene ring (at position *3). In the compound according to this embodiment, when (L1)n is a single bond, the bonding configuration of (ii) (the bonding configuration between the ring structure represented by the general formula (12) and L1) will be explained using the following compound X4 as an example. In the general formula (12), compound X4 represents R 24 and R 25 The group, R 25 and R 26 The set, and R 26 and R 27 The set of atoms is bonded to each other to form an unsubstituted fused ring, and the atoms constituting the formed fused ring (at position *2) are directly bonded to the atoms constituting the benzanthracene ring (at position *4).

[0126] [ka]

[0127] In the compound according to this embodiment, R1 to R 12 Preferably, one of these is a group represented by the general formula (11).

[0128] In the compounds according to this embodiment, the compound represented by general formula (1) is preferably a compound represented by the following general formula (1A) or (1B).

[0129] [ka]

[0130] (In the above general formula (1A) or (1B), R1 to R 12 Ar, L1, and n are each independently R1 to R in the general formulas (1) and (11) above. 12 (This is synonymous with Ar, L1, and n.)

[0131] In the compound according to this embodiment, R7 in the general formula (1A) is a hydrogen atom. In the general formula (1B), R 12 It is preferable that it be a hydrogen atom.

[0132] In the compound according to this embodiment, the compound represented by general formula (1) is also preferably the compound represented by the following general formula (1C).

[0133] [ka]

[0134] (In the above general formula (1C), R1~R3, R5~R 12 Ar, L1, and n are, independently of each other, R1~R3 ​​and R5~R in the general formulas (1) and (11) above. 12 (This is synonymous with Ar, L1, and n.)

[0135] In the compound according to this embodiment, in the general formula (1C), R1 to R3 and R5 to R 12 , is preferably a hydrogen atom.

[0136] In the compound according to this embodiment, the group represented by general formula (11) is preferably a group represented by any of the following general formulas (111) to (116).

[0137] [ka]

[0138] (In the above general formulas (111) to (116), L1, n and R 22 ~R 27 These are, independently, L1, n, and R in the general formulas (11) and (12) above. 22 ~R 27 This is synonymous with the above general formula (1), where * indicates the bond position with the benzanthracene ring.

[0139] In the above general formulas (111) to (116), R 23 ~R 27 It is preferable that no pairs of adjacent elements are combined with each other. In the above general formulas (111) to (116), R 23 ~R 27 It is also preferable that one or more pairs of adjacent elements from among them combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring.

[0140] In the compound according to this embodiment, the group represented by general formula (11) is preferably a group represented by any of the following general formulas (117) to (129).

[0141] [ka]

[0142] (In the above general formulas (117) to (119), L1 and n are, independently, equivalent to L1 and n in the above general formula (11), R 23 ~R 24 , R 27 and R 221 ~R 224 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 bind to each other, Regarding the combination with L1 in the general formula (119), (iv)R 23 ~R 24 , R 27 and R 221 ~R 224 If one or more adjacent pairs of atoms from among them form a substituted or unsubstituted monoring, then L1 will bond to one of the atoms. (v)R 23 ~R 24 , R27 and R 221 ~R 224 Either one or more pairs of adjacent atoms from among them form a substituted or unsubstituted fused ring, and an atom constituting that ring is bonded to L1, (vi) R that does not form the substituted or unsubstituted monoring and the substituted or unsubstituted condensed ring. 24 , R 27 and R 221 ~R 224 One of these is a single bond that connects to L1, In the above general formulas (117) to (119), R is not a single bond that bonds with L1. 22 , and R that does not form the substituted or unsubstituted monoring, does not form the substituted or unsubstituted fused ring, and is not a single bond bonded to L1. 23 ~R 24 , R 27 and R 221 ~R 224 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 ) 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. * indicates the bonding position with the benzanthracene ring in the general formula (1). In the general formula (119), ** is the bonding position with the atom constituting the monoring in case (iv), or the bonding position with the atom constituting the fused ring in case (v), or R 24 , R 27 and R 221 ~R 224 (This indicates the bond position with the single bond if any of the bonds are single bonds.)

[0143] In the above general formulas (117) to (119), R 23 ~R 24 , R 27 and R 221 ~R 224 It is preferable that no pairs of adjacent elements are combined with each other. In the above general formulas (117) to (119), R 23 ~R 24 , R 27 and R 221 ~R 224 It is also preferable that one or more pairs of adjacent elements from among them combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring.

[0144] [ka]

[0145] (In the above general formulas (120) to (123), L1 and n are, independently, equivalent to L1 and n in the above general formula (11), R 23 and R 225 ~R 232 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 bind to each other, Regarding the combination with L1 in the above general formulas (122) and (123), (vii)R 23 and R 225 ~R 232 If one or more adjacent pairs of atoms from among them form a substituted or unsubstituted monoring, then L1 will bond to one of the atoms. (viii)R 23 and R 225 ~R 232 Either one or more pairs of adjacent atoms from among them form a substituted or unsubstituted fused ring, and an atom constituting that ring is bonded to L1, (ix) R that does not form the substituted or unsubstituted monoring and the substituted or unsubstituted condensed ring. 225 ~R 232 One of these is a single bond that connects to L1, In the above general formulas (120) to (123), R is not a single bond that bonds with L1. 22 , and R that does not form the substituted or unsubstituted monoring, does not form the substituted or unsubstituted fused ring, and is not a single bond bonded to L1. 23 and R 225 ~R 232 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 ) 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. * indicates the bonding position with the benzanthracene ring in the general formula (1). In the general formulas (122) and (123), ** is the bonding position with the atom constituting the monoring in case (vii), or the bonding position with the atom constituting the fused ring in case (viii), or R 225 ~R 232 (This indicates the bond position with the single bond if any of the bonds are single bonds.)

[0146] In the above general formulas (120) to (123), R 23 and R 225 ~R 232 It is preferable that no pairs of adjacent elements are combined with each other. In the above general formulas (120) to (123), R 23 and R 225 ~R 232 It is also preferable that one or more pairs of adjacent elements from among them combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring.

[0147] [ka]

[0148] (In the above general formulas (124) to (126), L1 and n are, independently, equivalent to L1 and n in the above general formula (11), R 23 ~R 25 and R229 ~R 232 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 bind to each other, Regarding the combination with L1 in the general formula (126) above, (x)R 23 ~R 25 and R 229 ~R 232 If one or more adjacent pairs of atoms from among them form a substituted or unsubstituted monoring, then L1 will bond to one of the atoms. (xi)R 23 ~R 25 and R 229 ~R 232 Either one or more pairs of adjacent atoms from among them form a substituted or unsubstituted fused ring, and an atom constituting that ring is bonded to L1, (xii) R that does not form the substituted or unsubstituted monoring and the substituted or unsubstituted condensed ring. 24 ~R 25 and R 229 ~R 232 One of these is a single bond that connects to L1, In the above general formulas (124) to (126), R is not a single bond that bonds with L1. 22 , and R that does not form the substituted or unsubstituted monoring, does not form the substituted or unsubstituted fused ring, and is not a single bond bonded to L1. 23 ~R 25 and R 229 ~R 232 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 ) 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. * indicates the bonding position with the benzanthracene ring in the general formula (1). In the general formula (126), ** is the bonding position with the atom constituting the monoring in case (x), or the bonding position with the atom constituting the fused ring in case (xi), or R 24 ~R 25 and R 229 ~R 232 (This indicates the bond position with the single bond if any of the bonds are single bonds.)

[0149] [ka]

[0150] (In the above general formulas (127) to (129), L1 and n are, independently, equivalent to L1 and n in the above general formula (11), R 23 ~R 25 and R 229 ~R 232 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 bind to each other, Regarding the combination with L1 in the general formula (129) above, (xiii)R 23 ~R 25 and R 229 ~R 232 If one or more adjacent pairs of atoms from among them form a substituted or unsubstituted monoring, then L1 will bond to one of the atoms. (xiv)R 23 ~R 25 and R 229 ~R 232 Either one or more pairs of adjacent atoms from among them form a substituted or unsubstituted fused ring, and an atom constituting that ring is bonded to L1, (xv) R that does not form the substituted or unsubstituted monoring and the substituted or unsubstituted condensed ring. 24 ~R 25 and R 229 ~R 232 One of these is a single bond that connects to L1, In the above general formulas (127) to (129), R is not a single bond that bonds with L1. 22 , and R that does not form the substituted or unsubstituted monoring, does not form the substituted or unsubstituted fused ring, and is not a single bond bonded to L1. 23 ~R 25 and R 229 ~R 232 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 904A base represented by ) -S-(R 905 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. * indicates the bonding position with the benzanthracene ring in the general formula (1). In the general formula (129), ** is the bonding position with the atom constituting the monoring in case (xiii), or the bonding position with the atom constituting the fused ring in case (xiv), or R 24 ~R 25 and R 229 ~R 232 (This indicates the bond position with the single bond if any of the bonds are single bonds.)

[0151] In the above general formulas (127) to (129), R 23 ~R 25 and R 229 ~R 232 It is preferable that no pairs of adjacent elements are combined with each other. In the above general formulas (127) to (129), R 23 ~R 25 and R 229 ~R 232 It is also preferable that one or more pairs of adjacent elements from among them combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring.

[0152] In the compound according to this embodiment, the group represented by general formula (11) is also preferably a group represented by any of the following general formulas (130) to (135).

[0153] [ka]

[0154] [ka]

[0155] (In the above general formulas (130) to (135), L1 and n are, independently, equivalent to L1 and n in the above general formula (11), R 23 and R 240 ~R 247 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 bind to each other, Regarding the combination with L1 in the general formulas (132) and (135) above, (L1)R 23 and R 240 ~R 247 If one or more adjacent pairs of atoms from among them form a substituted or unsubstituted monoring, then L1 will bond to one of the atoms. (L2)R 23 and R 240 ~R 247 Either one or more pairs of adjacent atoms from among them form a substituted or unsubstituted fused ring, and an atom constituting that ring is bonded to L1, (L3) R that does not form the substituted or unsubstituted monoring and the substituted or unsubstituted condensed ring. 240 ~R 247 One of these is a single bond that connects to L1, In the above general formulas (130) to (135), R is not a single bond that bonds with L1. 22 , and R that does not form the substituted or unsubstituted monoring, does not form the substituted or unsubstituted fused ring, and is not a single bond bonded to L1. 23 and R 240~R 247 Each of them operates independently. In the above general formula (117), R 23 It is synonymous with, * indicates the bonding position with the benzanthracene ring in the general formula (1). In the general formulas (132) and (135), ** is the bonding position with the atom constituting the monoring in the case of (L1), or the bonding position with the atom constituting the fused ring in the case of (L2), or R 240 ~R 247 (This indicates the bond position with the single bond if any of the bonds are single bonds.)

[0156] In the above general formulas (130) to (135), R 23 and R 240 ~R 247 It is preferable that no pairs of adjacent elements are combined with each other. In the above general formulas (130) to (135), R 23 and R 240 ~R 247 It is also preferable that one or more pairs of adjacent elements from among them combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring. In the above general formulas (130) to (135), R 22 , R 23 and R 240 ~R 247 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C14 alkyl group, a substituted or unsubstituted ring-forming C3-C14 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C14 aryl group, or a substituted or unsubstituted ring-forming C5-C14 heterocyclic group.

[0157] In the compound according to this embodiment, with respect to the bond between the ring structure represented by the general formula (12) and L1 in the general formula (11), R 22 or R 23 It is preferable that the bond with L1 is a single bond. In the compound according to this embodiment, the group represented by general formula (11) is preferably a group represented by any of the general formulas (111) to (112), (117) to (118), (120) to (121), (124) to (125), (127) to (128), (130) to (131), and (133) to (134).

[0158] In the compound according to this embodiment, R 22 ~R 27 and R 221 ~R 232 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C14 alkyl group, a substituted or unsubstituted ring-forming C3-C14 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C14 aryl group, or a substituted or unsubstituted ring-forming C5-C14 heterocyclic group.

[0159] In the compound according to this embodiment, R1 to R 12 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 14 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, or a group represented by the general formula (11). In the compound according to this embodiment, R1 to R 12 One of them is the group represented by the general formula (11), and R1~R is not the group represented by the general formula (11). 12 Each of these is preferably independently a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 14 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, and is not a group represented by the general formula (11) above. 12 These are more preferably a hydrogen atom and an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, respectively. In the compound according to this embodiment, R1 to R 12 One of them is the group represented by the general formula (11), and R1~R is not the group represented by the general formula (11). 12It is also preferable that it be a hydrogen atom. In the compound according to this embodiment, R 22 ~R 27 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C14 alkyl group, a substituted or unsubstituted ring-forming C3-C14 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C14 aryl group, or a substituted or unsubstituted ring-forming C5-C14 heterocyclic group. In the compound according to this embodiment, R does not bond to L1. 22 ~R 23 Each of these is preferably a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, and more preferably a hydrogen atom or an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms.

[0160] In the compound according to this embodiment, n is preferably 0 or 1.

[0161] In the compound according to this embodiment, L1 is preferably a single bond, or a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms. In the compound according to this embodiment, L1 is preferably a single-bonded, substituted, or unsubstituted divalent heterocyclic group having 5 to 18 ring-forming atoms, or a substituted or unsubstituted arylene group having 6 to 18 ring-forming carbon atoms.

[0162] In the compounds according to this embodiment, it is preferable that any group described as "substituted or unsubstituted" is an "unsubstituted" group.

[0163] (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.

[0164] (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.

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[0278] [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.

[0279] [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.

[0280] The first light-emitting layer of the organic EL element according to this embodiment contains the compound according to the first embodiment (a compound represented by general formula (1)) as the first host material.

[0281] (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.

[0282] 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.

[0283] (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.

[0284] 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.

[0285] 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.

[0286] 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.

[0287] 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.

[0288] 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.

[0289] 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.

[0290] 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).

[0291] 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.

[0292] 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)

[0293] 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.

[0294] In the organic EL element according to this embodiment, it is preferable that the lowest excited singlet energy S1(H1) of the first host material and the lowest excited singlet energy S1(D1) of the first luminescent compound satisfy the relationship shown in the following formula (Equation 5). The lowest excited singlet energy S1 refers to the energy difference between the lowest excited singlet state and the ground state. S1(H1)>S1(D1) …(Math 5)

[0295] 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.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] (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.

[0300] 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.

[0301] 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.

[0302] In the organic EL element according to this embodiment, it is preferable that the second luminescent compound exhibits emission with a maximum peak wavelength of 500 nm or less. It is preferable that the first luminescent compound and the second luminescent compound each independently exhibit emission with a maximum peak wavelength of 500 nm or less.

[0303] 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.

[0304] 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.

[0305] 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.

[0306] 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.

[0307] 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)

[0308] Conventionally, Triplet-Triplet-Annihilation (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 8.

[0309] 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%.

[0310] 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), and it is preferable that 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 shown in 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.

[0311] In an organic EL element according to one aspect of 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 following equation (Equation 1B). T1(H1)-T1(H2)>0.03eV …(Math 1B)

[0312] 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.

[0313] 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.

[0314] 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)

[0315] In the organic EL element according to this embodiment, it is preferable that the lowest excited singlet energy S1(H2) of the second host material and the lowest excited singlet energy S1(D2) of the second luminescent compound satisfy the relationship shown in the following formula (Equation 7). S1(H2)>S1(D2)…(Number 7)

[0316] 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 lowest singlet excitation energy S1(D2) of the second luminescent compound is smaller than the lowest singlet excitation energy S1(H2) 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.

[0317] 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)

[0318] 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.

[0319] 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.

[0320] 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.

[0321] 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.

[0322] 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.

[0323] 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.

[0324] 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.

[0325] 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. The second light-emitting layer may contain only one type of second light-emitting compound, or two or more types.

[0326] 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.

[0327] 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.

[0328] 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.

[0329] 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.

[0330] 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.

[0331] 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 preferable that 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.

[0332] 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)

[0333] 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)

[0334] 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 mobility evaluation element configuration 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).

[0335] [ka]

[0336] 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].

[0337] 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 mobility evaluation element configuration 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).

[0338] [ka]

[0339] 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].

[0340] 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.

[0341] 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.

[0342] 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.

[0343] (Second host material) In an organic EL element according to one aspect of this embodiment, the second host material is not particularly limited, but examples include a second compound represented by the following general formula (2).

[0344] (Second compound) In an organic EL element according to one aspect of this embodiment, the second host material is preferably a second compound represented by the following general formula (2).

[0345] [ka]

[0346] (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.

[0347] (In the second host material, R 901 , R 902 , R 903 , R 904 , R 905 , R906 , 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 801 They are either identical or different from one another. R 802 If multiple R 802 They are either identical or different to one another.

[0348] 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.

[0349] In the organic EL element according to this embodiment, L 201 and L 202Each 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.

[0350] 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.

[0351] 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).

[0352] [ka]

[0353] [ka]

[0354] [ka]

[0355] [ka]

[0356] [ka]

[0357] [ka]

[0358] [ka]

[0359] [ka]

[0360] [ka]

[0361] (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...)

[0362] 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).

[0363] [ka]

[0364] [ka]

[0365] [ka]

[0366] [ka]

[0367] [ka]

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371] [ka]

[0372] (In the above general formulas (221), (222), (223), (224), (225), (226), (227), (228), and (229), R 201 R 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.

[0373] 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).

[0374] [ka]

[0375] [ka]

[0376] [ka]

[0377] [ka]

[0378] [ka]

[0379] [ka]

[0380] [ka]

[0381] [ka]

[0382] [ka]

[0383] (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. 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.

[0384] In the second compound represented by the general formula (2) above, 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 preferable that the group is represented by ).

[0385] 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 this is a substituted or unsubstituted ring-forming aryl group having 6 to 22 carbon atoms.

[0386] 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 208 When 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 907A 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.

[0387] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), 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 also preferable that the group be represented by ).

[0388] In the organic EL element according to this embodiment, in the second compound represented by the general formula (2), R 201 ~R 208 It is preferable that it be a hydrogen atom.

[0389] In the second compound, R 201 ~R 208In 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.

[0390] 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 208 When 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.

[0391] In the second compound, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0392] (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.

[0393] (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.

[0394] [ka]

[0395] [ka]

[0396] [ka]

[0397] [ka]

[0398] [ka]

[0399] [ka]

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[0422] [ka]

[0423] (First luminescent compound and second luminescent compound) In the following explanation, unless otherwise specified, the first luminescent compound and the second luminescent compound will be collectively referred to as "luminescent compounds." In the organic EL element according to this embodiment, examples of luminescent compounds include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluorantene derivatives, aryl-substituted fluorantene derivatives, indenoperylene derivatives, acenaphthofluorantene derivatives, compounds containing boron atoms, pyrometenoboron complex compounds, compounds having a pyrometene skeleton, metal complexes of compounds having a pyrometene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0424] Examples of luminescent compounds include, Compounds represented by the following general formula (4), Compounds represented by the following general formula (5), Compounds represented by the following general formula (6), and One or more compounds selected from the group consisting of compounds represented by the following general formula (8) are mentioned.

[0425] (Compounds represented by general formula (4)) This section describes compounds represented by general formula (4).

[0426] [ka]

[0427] (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 bind to 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 bind to 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 bind to each other, Ra, Rb, and Rc, which do not form the monoring and do not form the condensed ring, 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(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.

[0428] The "aromatic hydrocarbon rings" of rings A1 and A2 have the same structure as the compounds in which a hydrogen atom is introduced into the "aryl group with 6 to 50 carbon atoms forming the ring" mentioned above. The "aromatic hydrocarbon rings" of rings A1 and A2 include two carbon atoms on the central condensed biring structure of general formula (4) as ring-forming atoms. Specific examples of "substituted or unsubstituted ring-forming aromatic hydrocarbon rings with 6 to 50 carbon atoms" include compounds in which a hydrogen atom has been introduced to the "substituted or unsubstituted aryl group" described in specific example group G1.

[0429] The heterocyclic rings of the A1 and A2 rings have the same structure as the compounds in which hydrogen atoms are introduced into the heterocyclic groups with 5 to 50 ring-forming atoms, as described above. The "heterocyclic rings" of the A1 and A2 rings include two carbon atoms on the central fused bicyclic ring structure of the general formula (4) as ring-forming atoms. Specific examples of "heterocyclic rings with 5 to 50 substituted or unsubstituted ring-forming atoms" include compounds in which hydrogen atoms have been introduced into the "substituted or unsubstituted heterocyclic groups" described in specific example group G2.

[0430] Rb is bonded to either one of the carbon atoms forming an aromatic hydrocarbon ring as an A1 ring, or to any of the atoms forming a heterocycle as an A1 ring.

[0431] Rc is bonded to either one of the carbon atoms forming an aromatic hydrocarbon ring as an A2 ring, or to any of the atoms forming a heterocycle as an A2 ring.

[0432] It is preferable that at least one of Ra, Rb, and Rc is a group represented by the following general formula (4a), and it is more preferable that at least two are groups represented by the following general formula (4a).

[0433] [ka]

[0434] (In the above general formula (4a), L 401 teeth, single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, Ar 401 teeth, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or It is a group represented by the following general formula (4b).

[0435] [ka]

[0436] (In the above general formula (4b), L 402 and L 403 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or A divalent heterocyclic group having 5 to 30 substituted or unsubstituted ring-forming atoms, Ar 402 and Ar 403 The group consisting of 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 bind to each other, Ar that does not form the aforementioned monoring and does not form the aforementioned condensed ring 402 and Ar 403 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.

[0437] In luminescent compounds, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group 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. In luminescent compounds, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 Each of them operates independently. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, It is preferable that the ring-forming aryl group has 6 to 50 carbon atoms and is either substituted or unsubstituted.

[0438] Examples of compounds represented by the general formula (4) include the following compounds.

[0439] [ka]

[0440] (Compound represented by general formula (5)) This section describes compounds represented by general formula (5).

[0441] [ka]

[0442] (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 bind to each other, R that does not form the aforementioned monoring and does not form the aforementioned 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 These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 521 and R 522 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0443] "R 501 ~R 507 and R 511 ~R 517 "A set of two or more adjacent elements" is, for example, R 501 and R 502 A group consisting of R 502 and R 503 A group consisting of R 503 and R 504 A group consisting of R 505 and R 506 A group consisting of R 506 and R 507 A group consisting of R 501 and R 502 and R 503 This is a combination of sets and other elements.

[0444] In one embodiment, R 501 ~R 507 and R 511 ~R 517 At least one, preferably two, of are -N(R 906 )(R 907 It is a base represented by ).

[0445] In one embodiment, R 501 ~R 507 and R 511 ~R 517 Each of them operates independently. hydrogen atom, 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.

[0446] Examples of compounds represented by the general formula (5) include the following compounds.

[0447] [ka]

[0448] [ka]

[0449] (Compounds represented by general formula (6)) This section describes compounds represented by general formula (6).

[0450] [ka]

[0451] (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.

[0452] Rings a, b, and c are rings that condense into the central condensed biring structure of general formula (6) consisting of a boron atom and two nitrogen atoms (substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 5 to 50 ring-forming atoms).

[0453] The aromatic hydrocarbon rings of rings a, b, and c have the same structure as the compounds in which a hydrogen atom is introduced into the aforementioned aryl group with 6 to 50 carbon atoms that forms the ring. The "aromatic hydrocarbon ring" of ring a includes three carbon atoms on the central condensed biring structure of general formula (6) as ring-forming atoms. The "aromatic hydrocarbon rings" of rings b and c include two carbon atoms on the central condensed two-ring structure of general formula (6) as ring-forming atoms.

[0454] Specific examples of "substituted or unsubstituted ring-forming aromatic hydrocarbon rings with 6 to 50 carbon atoms" include compounds in which a hydrogen atom has been introduced to the "substituted or unsubstituted aryl group" described in specific example group G1. The heterocyclic rings of the a, b, and c rings have the same structure as compounds in which hydrogen atoms are introduced into the heterocyclic groups with 5 to 50 ring-forming atoms, as described above. The heterocycle of ring a includes three carbon atoms on the central fused biring structure of general formula (6) as ring-forming atoms. The heterocycles of rings b and c include two carbon atoms on the central fused biring structure of general formula (6) as ring-forming atoms. Specific examples of "heterocycles with 5 to 50 substituted or unsubstituted ring-forming atoms" include compounds in which hydrogen atoms are introduced into the "substituted or unsubstituted heterocyclic groups" described in specific example group G2.

[0455] R 601 and R 602 Each of these may independently bond with a ring a, a ring b, or a ring c to form a substituted or unsubstituted heterocycle. In this case, the heterocycle contains a nitrogen atom on the central fused biring structure of general formula (6). In this case, the heterocycle may also contain heteroatoms other than nitrogen. 601 and R 602 Specifically, when it is said that it bonds with ring a, ring b, or ring c, it means that it bonds with an atom constituting ring a, ring b, or ring c and R 601 and R 602 This means that the atoms that make up the compound are bonded together. For example, R 601 It binds to the a ring, R 601A nitrogen-containing heterocycle of two-ring condensation (or three-ring condensation or more) may be formed by the condensation of a ring containing a nitrogen ring with an a-ring. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to two-ring condensation or more heterocyclic groups containing nitrogen. R 601 When it bonds with the b ring, R 602 When it bonds with the a ring, and R 602 The same applies when it is bonded to a c-ring.

[0456] In one embodiment, the a-ring, b-ring, and c-ring in the general formula (6) are each independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring-forming carbon atoms. In one embodiment, the a-ring, b-ring, and c-ring in the general formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

[0457] In one embodiment, R in the general formula (6) 601 and R 602 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Preferably, it is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms that forms a ring.

[0458] In one embodiment, the compound represented by the general formula (6) is the compound represented by the following general formula (62).

[0459] [ka]

[0460] (In the above general formula (62), R 601A R 611 and R 621 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R602A R 613 and R 614 It combines with one or more elements selected from the group consisting of to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R that does not form the aforementioned substituted or unsubstituted heteroalgebra 601A and R 602A Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 611 ~R 621 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the substituted or unsubstituted heterocycle, does not form the monocycle, and does not form the fused ring. 611 ~R 621 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0461] R in the above general formula (62) 601A and R 602A These are, respectively, R in the general formula (6) above. 601 and R 602 It is the corresponding base. For example, R 601A and R 611 These may bond to form a two-ring condensation (or three-ring condensation or more) nitrogen-containing heterocycle in which the ring containing these and the benzene ring corresponding to the a-ring are fused. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to two-ring condensation or more heterocycle groups containing nitrogen. 601A and R 621 When they are joined, R 602A and R 613 When they are joined, and R 602A and R 614 The same applies when they are joined together.

[0462] R 611 ~R 621 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a substituted or unsubstituted monoring, or They may bond to each other to form substituted or unsubstituted fused rings. For example, R 611 and R 612 These rings may bond together to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring, or benzothiophene ring is fused to the six-membered ring to which they are bonded. The resulting fused ring may be a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring.

[0463] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 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.

[0464] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. hydrogen atom, 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.

[0465] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. Hydrogen atom, or These are substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms.

[0466] In one embodiment, R does not contribute to ring formation. 611 ~R 621 Each of them operates independently. Hydrogen atom, or A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 611 ~R 621 At least one of these is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0467] In one embodiment, the compound represented by the general formula (62) is the compound represented by the following general formula (63).

[0468] [ka]

[0469] (In the above general formula (63), R 631 R 646 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 633 R 647 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 634 R 651 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 641 R 642 It combines with to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 631 ~R 651 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 bind to each other, R that does not form the substituted or unsubstituted heterocycle, does not form the monocycle, and does not form the fused ring. 631 ~R 651 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905A base represented by ) -N(R 906 )(R 907 A base represented by ) halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0470] R 631 R 646 It may be combined with to form a substituted or unsubstituted heterocyclic ring. For example, R 631 and R 646 They combine, R 646 A nitrogen-containing heterocycle of three or more rings may be formed by the condensation of a benzene ring to which the nitrogen is bonded, a ring containing nitrogen, and a benzene ring corresponding to the a-ring. Specific examples of such nitrogen-containing heterocycles include compounds from specific example group G2 that correspond to three or more heterocyclic groups containing nitrogen. 633 and R 647 When they are joined, R 634 and R 651 When they are joined, and R 641 and R 642 The same applies when they are joined together.

[0471] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 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.

[0472] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. hydrogen atom, 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.

[0473] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. Hydrogen atom, or These are substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms.

[0474] In one embodiment, R does not contribute to ring formation. 631 ~R 651 Each of them operates independently. Hydrogen atom, or A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 631 ~R 651 At least one of these is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0475] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63A).

[0476] [ka]

[0477] (In the above general formula (63A), R 661 teeth, 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, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 662 ~R 665 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, (These are substituted or unsubstituted aryl groups with 6 to 50 carbon atoms forming a ring.)

[0478] In one embodiment, R 661 ~R 665 Each of them operates independently. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.

[0479] In one embodiment, R 661 ~R 665 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0480] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63B).

[0481] [ka]

[0482] (In the above general formula (63B), R 671 and R 672 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, -N(R 906 )(R 907 A base represented by ) or A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 673 ~R 675 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, -N(R 906 )(R 907 A base represented by ) or (These are substituted or unsubstituted aryl groups with 6 to 50 carbon atoms forming a ring.)

[0483] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63B').

[0484] [ka]

[0485] (In the above general formula (63B'), R 672 ~R 675 Each of these independently corresponds to R in the general formula (63B) 672 ~R 675 (This is synonymous with...)

[0486] In one embodiment, R 671 ~R 675 At least one of them is 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, -N(R 906 )(R 907 A base represented by ) or These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.

[0487] In one embodiment, R 672 teeth, hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) or A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, R 671 and R 673 ~R 675 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, -N(R 906 )(R 907 A base represented by ) or These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.

[0488] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63C).

[0489] [ka]

[0490] (In the above general formula (63C), R 681 and R 682 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, These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms. R683 ~R 686 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, (These are substituted or unsubstituted aryl groups with 6 to 50 carbon atoms forming a ring.)

[0491] In one embodiment, the compound represented by the general formula (63) is the compound represented by the following general formula (63C').

[0492] [ka]

[0493] (In the above general formula (63C'), R 683 ~R 686 Each of these independently corresponds to R in the general formula (63C) 683 ~R 686 (This is synonymous with...)

[0494] In one embodiment, R 681 ~R 686 Each of them operates independently. A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, These are substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.

[0495] In one embodiment, R 681 ~R 686 These are, independently, substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms.

[0496] The compound represented by the general formula (6) is first formed by linking the a-ring, b-ring, and c-ring with a linking group (NR 601 Groups including NR 602An intermediate can be produced by bonding the rings with a group containing a boron atom (first reaction), and the final product can be produced by bonding the a, b, and c rings with a linking group (a group containing a boron atom) (second reaction). In the first reaction, amination reactions such as the Bachbrutt-Hartwig reaction can be applied. In the second reaction, tandem hetero-Friedel-Crafts reactions can be applied.

[0497] 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.

[0498] [ka]

[0499] [ka]

[0500] [ka]

[0501] [ka]

[0502] [ka]

[0503] [ka]

[0504] [ka]

[0505] [ka]

[0506] [ka]

[0507] [ka]

[0508] [ka]

[0509] [ka]

[0510] [ka]

[0511] (Compounds represented by general formula (8)) This section describes compounds represented by general formula (8).

[0512] [ka]

[0513] (In the above general formula (8), R 801 and R 802 , R 802 and R 803 , and R 803 and R 804 At least one pair of these combines with each other to form a divalent group represented by the following general formula (82): R 805 and R 806 , R 806 and R 807 , and R 807 and R 808At least one set of them combines with each other to form a divalent group represented by the following general formula (83).)

[0514] [Chemical formula]

[0515] (R that does not form the divalent group represented by the general formula (82) 801 ~R 804 , and R 811 ~R 814 At least one of them is a monovalent group represented by the following general formula (84), R that does not form the divalent group represented by the general formula (83) 805 ~R 808 , and R 821 ~R 824 At least one of them is a monovalent group represented by the following general formula (84),[[ID=①]] X8 is an oxygen atom, a sulfur atom, or NR 809 and R that does not form the divalent groups represented by the general formula (82) and the general formula (83), and is not the monovalent group represented by the general formula (84) 801 ~R 808 , R that is not the monovalent group represented by the general formula (84) 811 ~R 814 and R 821 ~R 824 , and R 809 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 Notes: 1. In the translation, the "①" in the original text is likely a mislabeled ID and should be "31" as per the sequential ID numbers in the original. This has been corrected in the translation for clarity. 2. The chemical formula placeholder "[[化]]" is translated as "[Chemical formula]" to maintain the context related to chemical content. 3. The specific chemical groups and formulas are translated as accurately as possible while following the rules of chemical nomenclature in English. For example, "アルキル基" is translated as "alkyl group", "アルケニル基" as "alkenyl group", "アルキニル基" as "alkynyl group", and "シクロアルキル基" as "cycloalkyl group". The formulas like "-Si(R)(R)(R)" and "-O-(R)" are translated to maintain their structural representation in English.a group represented by -N(R 906 )(R 907 ) represents a group, 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. )

[0516] [Chemical formula]

[0517] <00045所において、(In the general formula (84), Ar 801 and Ar 802 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, L 801 ~L 803 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or a divalent linking group formed by bonding of 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, * in the general formula (84) indicates the bonding position with the ring structure represented by the general formula (8), the group represented by the general formula (82) or the general formula (83). )

[0518] In the general formula (8), the positions where the divalent group represented by the general formula (82) and the divalent group represented by the general formula (83) are formed are not particularly limited, and the group can be formed at possible positions of R 801 ~R 808 .

[0519] In addition to the compounds listed in International Publication No. 2014 / 104144, specific examples of compounds represented by the general formula (8) include the following compounds.

[0520] [ka]

[0521] In addition to the compounds represented by general formulas (4), (5), (6), and (8) mentioned above, other compounds such as those listed below can also be used as luminescent compounds.

[0522] [ka]

[0523] [ka]

[0524] [ka]

[0525] [ka]

[0526] (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 light-emitting band. 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. The organic EL element according to this embodiment may have a hole transport layer between the anode and the light-emitting band. The organic EL element according to this embodiment may have an electron transport layer between the cathode and the light-emitting band.

[0527] In the organic EL element according to this embodiment, the element may consist only of the light-emitting band, 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.

[0528] 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.

[0529] 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.

[0530] 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.

[0531] The present invention is not limited to the configuration of the organic EL element shown in Figures 1, 2, and 3.

[0532] (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.

[0533] (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).

[0534] 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.

[0535] 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.

[0536] Materials with a low work function include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg). Alkaline earth metals such as calcium (Ca) and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them can also be used. When forming the anode using alkali metals, alkaline earth metals, and alloys containing them, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or the like, coating methods or inkjet methods can be used.

[0537] (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.

[0538] 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.

[0539] 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.

[0540] (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.

[0541] 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).

[0542] 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.

[0543] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. 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.

[0544] 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.

[0545] 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.

[0546] (electron transport layer) In the organic EL element according to the above embodiment, it is preferable to include an electron transport layer between the light-emitting layer and the cathode. The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, low-molecular-weight organic compounds 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, among others, 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 the above 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.

[0547] 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.

[0548] (electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer can contain alkali metals, alkaline earth metals, or compounds thereof, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). Alternatively, a material containing an alkali metal, alkaline earth metal, or compound thereof in an electron-transporting material, specifically one containing magnesium (Mg) in Alq, may also be used. In this case, electron injection from the cathode can be performed more efficiently.

[0549] 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.

[0550] (Layer formation method) The method for forming each layer of the organic EL element in the above 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.

[0551] (film thickness) The film thickness of each organic layer in the organic EL element of the above 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.

[0552] (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).

[0553] [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.

[0554] [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.

[0555] 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.

[0556] 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.

[0557] 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]

[0558] The following describes examples of the present invention. The present invention is not limited in any way by these examples.

[0559] <Compound> The structure of the compound represented by general formula (1) used in the manufacture of the organic EL element according to the example is shown below.

[0560] [ka]

[0561] [ka]

[0562] <Fabrication of Organic EL Devices> [Example 1] An organic EL device according to Example 1 was fabricated, containing compound BH1-1 in the light-emitting layer.

[0563] [Examples 2-8] The organic EL elements in Examples 2 to 8 were fabricated in the same manner as in Example 1, except that compound BH1-1 was replaced with compounds BH1-2 to BH1-8.

[0564] <Example of synthesis> (Synthesis Example 1: Synthesis of BH1-1)

[0565] [ka]

[0566] Compound 1 (3.00 g), Compound 2 (1.74 g), and PdCl2(Amphos)2 (0.28 g) were placed in a flask, purged with argon gas, and then 1,4-dioxane (98 mL) and 2 M aqueous sodium carbonate solution (12.2 mL) were added. The mixture was heated and stirred under reflux conditions for 6 hours. The solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography and washed with dimethoxyethane to obtain BH1-1 as a white solid (1.45 g, yield 43%). Mass spectral analysis revealed a molecular weight of 344.41 and a m / e ratio of 345, identifying it as the target substance.

[0567] (Synthesis Example 2: Synthesis of BH1-2)

[0568] [ka]

[0569] BH1-2 was synthesized using the same method as in the synthesis of BH1-1, except that Compound 3 was used instead of Compound 2, and BH1-2 was obtained as a white solid (1.72 g, yield 51%). Mass spectral analysis revealed a molecular weight of 344.41 and a m / e ratio of 345, identifying it as the target substance.

[0570] (Synthesis Example 3: Synthesis of BH1-3)

[0571] [ka]

[0572] Compound 4 (2.50 g), Compound 5 (2.10 g), Pd2(dba)3 (0.17 g), and SPhos (0.30 g) were placed in a flask, purged with argon gas, and then 1,4-dioxane (92 mL) and 2 M sodium carbonate aqueous solution (11.5 mL) were added. The mixture was heated and stirred under reflux conditions for 8 hours. The solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography. BH1-3 was obtained as a white solid (2.24 g, yield 58%) by washing with hexane and dimethoxyethane. Mass spectral analysis revealed a molecular weight of 420.51 and a m / e ratio of 421, identifying it as the target substance.

[0573] (Synthesis Example 4: Synthesis of BH1-4)

[0574] [ka]

[0575] In the synthesis of BH1-3, the same method was used except that Compound 6 was used instead of Compound 5, and BH1-4 was obtained as a white solid (2.92 g, yield 64%). Mass spectral analysis revealed a molecular weight of 496.60 and a m / e ratio of 497, identifying it as the target substance.

[0576] (Synthesis Example 5: Synthesis of BH1-5)

[0577] [ka]

[0578] In the synthesis of BH1-3, the same method was used except that Compound 7 was used instead of Compound 5, and BH1-5 was obtained as a white solid (1.92 g, yield 42%). Mass spectral analysis revealed a molecular weight of 496.60 and a m / e ratio of 497, identifying it as the target substance.

[0579] (Synthesis Example 6: Synthesis of BH1-6)

[0580] [ka]

[0581] In the synthesis of BH1-3, the same method was used except that Compound 8 was used instead of Compound 5, and BH1-6 was obtained as a white solid (1.27 g, yield 33%). Mass spectral analysis revealed a molecular weight of 420.51 and a m / e ratio of 421, identifying it as the target substance.

[0582] (Synthesis Example 7: Synthesis of BH1-7) (1) Synthesis of Compound11

[0583] [ka]

[0584] Compound 9 (5.00 g), Compound 10 (2.58 g), Pd(PPh3)4 (0.48 g), and CuI (0.04 g) were placed in a flask, purged with argon gas, and triethylamine (42.2 mL) was added. The mixture was heated and stirred at 80°C for 5 hours. After the reaction solution was cooled to room temperature, water, dichloromethane, and hexane were added, and the oil layer was extracted. The solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography to obtain Compound 11 as a yellow solid (4.51 g, yield 82%). Mass spectral analysis revealed a molecular weight of 258.32 and a m / e ratio of 259, identifying it as the target substance.

[0585] (2) Synthesis of Compound12

[0586] [ka]

[0587] Compound 11 (3.95 g) was placed in a flask, purged with argon gas, and then dichloromethane (76 mL) was added. While stirring at room temperature, ICl (18.3 mL of 1 M dichloromethane solution) was added and the mixture was stirred at room temperature for 7 hours. After adding aqueous Na2SO3 solution, the oil layer was extracted with dichloromethane. The solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography to obtain Compound 12 as a white solid (2.58 g, yield 46%). Mass spectral analysis revealed a molecular weight of 370.18 and a m / e ratio of 371, identifying it as the target substance.

[0588] (3) Synthesis of BH1-7

[0589] [ka]

[0590] Compound 4 (2.57 g), Compound 12 (2.18 g), Pd2(dba)3 (0.10 g), SPhos (0.19 g), and Cs2CO3 (3.84 g) were placed in a flask, purged with argon gas, and then 1,4-dioxane (50 mL) and water (8.4 mL) were added. The mixture was heated and stirred under reflux conditions for 8 hours. The solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography. BH1-7 was obtained as a white solid (0.79 g, yield 24%) by washing with hexane, toluene, and dimethoxyethane. Mass spectral analysis revealed a molecular weight of 470.57 and a m / e ratio of 471, identifying it as the target substance.

[0591] (Synthesis Example 8: Synthesis of BH1-8)

[0592] [ka]

[0593] BH1-8 was synthesized using the same method as in the synthesis of BH1-1, except that Compound 13 was used instead of Compound 2, and was obtained as a pale yellow solid (2.25 g, yield 52%). Mass spectral analysis revealed a molecular weight of 444.53 and a m / e ratio of 445, identifying it as the target substance. [Explanation of Symbols]

[0594] 1...Organic electroluminescent element, 1A...Organic electroluminescent element, 1B...Organic electroluminescent element, 2...Substrate, 3...Anode, 4...Cathode, 5...Emission band, 5A...Emission band, 5B...Emission band, 6...Hole injection layer, 7...Hole transport layer, 8...Electron transport layer, 9...Electron injection layer, 10...Organic layer, 10A...Organic layer, 10B...Organic layer, 51...First emission layer, 52...Second emission layer.

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