Compounds, light-emitting materials, organic electroluminescent elements, and electronic devices

Abstract

To provide a compound that enables organic electroluminescent elements to emit light with high efficiency and long lifespan. [Solution] Specifically, for example, the following three compounds are shown. TIFF2026098156000179.tif56159

Description

[Technical Field]

[0001] The present invention relates to compounds, light-emitting materials, 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-type 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. Examples of OLED performance include brightness, emission wavelength, full width at half maximum, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0003] For example, it is expected that using triplet excitons in addition to singlet excitons will make organic EL devices emit light even more efficiently. Against this backdrop, highly efficient fluorescent organic EL devices utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being researched. The TADF (Thermally Activated Delayed Fluorescence) mechanism utilizes the phenomenon where reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when using materials with a small energy difference (ΔST) between the singlet and triplet energy levels. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors," edited by Chihaya Adachi, Kodansha, published April 1, 2012, pp. 261-268. Examples of compounds that exhibit thermally activated delayed fluorescence (TADF) include those in which a donor site and an acceptor site are bound together within the molecule.

[0004] For example, Patent Document 1 can be cited as a document relating to organic EL elements and compounds used in organic EL elements. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] International Publication No. 2021 / 215446 [Overview of the project] [Problems that the invention aims to solve]

[0006] Further performance improvements are needed for organic EL elements that utilize the TADF mechanism. The object of the present invention is to provide a compound that can enable an organic electroluminescent element to emit light with high efficiency and long lifespan, a light-emitting material containing the compound, an organic electroluminescent element that emits light with high efficiency and long lifespan, and an electronic device equipped with the organic EL element. [Means for solving the problem]

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

[0008] [ka]

[0009] (In the above general formula (1), R 101 ~R 111 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, An alkenyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted, A cycloalkenyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, An alkynyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted, -O-(R 190 ) group represented by -S-(R 191 ) group represented by An aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, A heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, -C(=O)-O-(R 192 ) group represented by -C(=O)-N(R 193 )(R 194 ) group represented by -N(R 195 )(R 196 ) group represented by Nitro group, and -Si(R 197 )(R 198 )(R 199 ) group represented by, selected from the group consisting of Ring A 1 , Ring B 1 and Ring C 1 are each independently An aromatic hydrocarbon ring having 6 to 30 ring-forming carbon atoms, which may be substituted or unsubstituted, or An aromatic heterocyclic ring having 5 to 30 ring-forming atoms, which may be substituted or unsubstituted, L 1 is a single bond, -O-, -S-, >C(R 112 )(R 113 ), or >Si(R 114 )(R 115 ), and R 112 and R 113 The group consisting of is a single bond, -O-, -S-, >C(R 112 )(R 113 ), >Si(R 114 )(R 115), via a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R 114 and R 115 and are single bonds, -O-, -S-, >C(R 112 )(R 113 ), >Si(R 114 )(R 115 ), via a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 112 ~R 115 Each of them operates independently. hydrogen atom, halogen atom, Substituted or unsubstituted ring-forming alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Selected from the group consisting of heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, however, (i)R 108 ~R 111 At least one of them is a cyano group, (ii) Ring B 1 and ring C 1 At least one of the rings is substituted with at least one cyano group, or (iii)R 108 ~R 111At least one of them is a cyano group, and ring B 1 and ring C 1 At least one of the rings is substituted with at least one cyano group. (In a compound having the structure represented by the general formula (1), R 190 ~R 199 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0010] According to one aspect of the present invention, a light-emitting material comprising 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 a cathode, an anode, and an organic layer contained between the cathode and the anode, wherein at least one layer of the organic layer contains a compound according to one aspect of the present invention as a first compound.

[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, it is possible to provide a compound that can enable an organic electroluminescent element to emit light with high efficiency and long lifespan, a light-emitting material containing the compound, an organic electroluminescent element that emits light with high efficiency and long lifespan, and an electronic device equipped with the organic EL element. [Brief explanation of the drawing]

[0014] [Figure 1]This figure shows a schematic configuration of an example of an organic electroluminescent element according to the third embodiment of the present invention. [Figure 2] This is a schematic diagram of a device for measuring transient PL (Power Level). [Figure 3] This figure shows an example of a transient PL decay curve. [Figure 4] This figure shows the energy levels of the first compound and the second compound in the light-emitting layer of an example of an organic electroluminescent element according to the third embodiment of the present invention, as well as the relationship between their energy transfers. [Figure 5] This figure shows the energy levels and energy transfer relationships of the first compound, the second compound, and the third compound in the light-emitting layer of an example of an organic electroluminescent element according to the fourth 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] ·Aryl group without substitution (specific example 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, Benzoanthryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzochrysenyl group, Triphenylenyl group, Benzotriphenylenyl group, Tetracenyl group, Pentacenyl group, Fluorenyl group, 9,9’-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perylenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0026] [Chemical formula]

[0027]

Chem.

[0028] ·Aryl group for substitution (specific example group G1B): o-Tolyl group, m-Tolyl group, p-Tolyl group, Para-Xylyl group, Meta-Xylyl group, Ortho-Xylyl group, Para-Isopropylphenyl group, Meta-Isopropylphenyl group, Ortho-Isopropylphenyl group, Para-t-Butylphenyl group, Meta-t-Butylphenyl group, Ortho-t-Butylphenyl group, 3,4,5-Trimethylphenyl group, 9,9-Dimethylfluorenyl group, 9,9-Diphenylfluorenyl group, 9,9-Bis(4-methylphenyl)fluorenyl group, 9,9-Bis(4-isopropylphenyl)fluorenyl group, 9,9-Bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group in which one or more hydrogen atoms of a monovalent group derived from the ring structures represented by the general formulas (TEMP-1) to (TEMP-15) are replaced by substituents.

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

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

[0056] ·「-O-(R 904 ) represented by the base The following information pertains to the -O-(R904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0057] · "-S-(R 905 ) represented by the base The following information pertains to the -S-(R 905 ) Examples of the base represented by (example group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0058] · "-N(R 906 )(R 907 ) represented by the base -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), 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 specifically refer to 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 pairs consisting of two or more adjacent ones are combined with each other to form a ring", the pair consisting of two adjacent ones that forms one pair is R 921 and R 922 and the pair of R 922 and R 923 and the pair of R 923 and R 924 and the pair of R 924 and R 930 and the pair of R 930 and R 925 and the pair of R 925 and R 926 and the pair of R 926 and R 927 and the pair of R 927 and R 928 and the pair of R 928 and R 929 and the pair of, and R 929 and R 921 and the pair of.

[0104] The above "one or more" means that two or more pairs consisting of two or more adjacent ones may form a ring at the same time. For example, R 921 and R 922 are combined with each other to form ring Q A , and at the same time R 925 and R 926 are combined with each other to form ring Q B is formed. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0105]

Chemical formula

[0106] The case where a "pair consisting of two or more adjacent ones" forms a ring includes not only the case where a pair consisting of "two" adjacent ones is combined as in the above example, but also the case where a pair consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form ring Q A , and R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C R 922 Share.

[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 Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R903 If there are two or more of them, then there are two or more R 903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.

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

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

[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 the first embodiment is a compound having a structure represented by the following general formula (1). The compound according to the first embodiment may be referred to as the first compound.

[0120] [ka]

[0121] (In the above general formula (1), R 101 ~R 111 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, -O-(R 190 ) a base represented by -S-(R 191 ) a base represented by 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, -C(=O)-O-(R 192 ) a base represented by -C(=O)-N(R 193 )(R 194 ) a base represented by -N(R 195 )(R 196 ) a base represented by Nitro group, and -Si(R 197 )(R 198 )(R 199 Selected from a group consisting of the groups represented by ), Ring A 1 , ring B 1 and ring C 1 Each of them operates independently. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 30 carbon atoms, or Aromatic heterocycles with 5 to 30 substituted or unsubstituted ring-forming atoms, L 1 These are single bonds, -O-, -S-, >C(R 112 )(R 113 ), or >Si(R 114 )(R 115 ) and R 112 and R 113 The combinations of these are single bonds, -O-, -S-, >C(R 112 )(R 113 ), >Si(R 114 )(R 115), via a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R 114 and R 115 and are single bonds, -O-, -S-, >C(R 112 )(R 113 ), >Si(R 114 )(R 115 ), via a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 112 ~R 115 Each of them operates independently. hydrogen atom, halogen atom, Substituted or unsubstituted ring-forming alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Selected from the group consisting of heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, however, (i)R 108 ~R 111 At least one of them is a cyano group, (ii) Ring B 1 and ring C 1 At least one of the rings is substituted with at least one cyano group, or (iii)R 108 ~R 111At least one of them is a cyano group, and ring B 1 and ring C 1 At least one of the rings is substituted with at least one cyano group. (In a compound having the structure represented by the general formula (1), R 190 ~R 199 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0122] In a compound having the structure represented by the general formula (1), R 190 If multiple R 190 They are either identical or different from each other, R 191 If multiple R 191 They are either identical or different from each other, R 192 If multiple R 192 They are either identical or different from each other, R 193 If multiple R 193 They are either identical or different from each other, R 194 If multiple R 194 They are either identical or different from each other, R 195 If multiple R 195 They are either identical or different from each other, R 196 If multiple R 196 They are either identical or different from each other, R 197 If multiple R 197 They are either identical or different from each other, R 198 If multiple R 198 They are either identical or different from each other, R 199 If multiple R 199 They are either identical or different from one another.

[0123] According to the compound of the first embodiment, an organic electroluminescent element can be made to emit light with high efficiency and long lifespan.

[0124] The compound according to the first embodiment has a cyano group at position (i), (ii), or (iii) in the molecule, resulting in a deeper ionization potential. By using the compound according to the first embodiment and a delayed fluorescence emitting material in the light-emitting layer, the efficiency of energy transfer from the delayed fluorescence emitting material to the compound according to the first embodiment is improved, and as a result, the luminescence efficiency of the organic EL element is expected to improve.

[0125] In the compound according to this embodiment, R 108 , R 109 , R 110 and R 111 Preferably, at least one of these substituents is selected from a substituent other than a hydrogen atom.

[0126] In the compound according to this embodiment, R 108 , R 109 , R 110 and R 111 Preferably, at least one of these is selected from substituted or unsubstituted alkyl groups, cyano groups, substituted or unsubstituted ring-forming aryl groups, and substituted or unsubstituted heterocyclic groups, each having 5 to 50 ring-forming atoms.

[0127] In the compound according to this embodiment, R 110 It is preferable that the substituent is selected from atoms other than hydrogen atoms.

[0128] In the compound according to this embodiment, R 110 It is preferable that the group is selected from substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, cyano groups, substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring-forming atoms.

[0129] In the compound according to this embodiment, the compound represented by the general formula (1) is L 1 When it is a single bond, it is represented by the following general formula (1A), L 1 If is -O-, it is represented by the following general formula (1B), L 1 If is -S-, it is expressed by the following general formula (1C), L 1 >C(R 112 )(R 113 If ), it is expressed by the following general formula (1D), L 1 ga>Si(R 114 )(R 115 If ), it is represented by the following general formula (1E).

[0130] [ka]

[0131] [ka]

[0132] [ka]

[0133] (In the above general formulas (1A) to (1E), R 101 ~R 111 , R 112 ~R 115 , ring A 1 , ring B 1 and ring C 1 These are, respectively, R in the general formula (1) above. 101 ~R 111 , R 112 ~R 115 , ring A 1 , ring B 1 and ring C 1 (This is synonymous with...)

[0134] In the compound according to this embodiment, L 1 It is preferable that the bond is a single bond.

[0135] The compound according to this embodiment is preferably represented by the general formula (1A).

[0136] The compounds according to this embodiment preferably contain at least one substituted or unsubstituted carbazolyl group in the molecule.

[0137] The compounds according to this embodiment preferably contain at least one substituted or unsubstituted N-carbazolyl group in the molecule.

[0138] In the compound according to this embodiment, ring A 1 , ring B 1 and ring C 1 It is preferable that at least one of the rings has at least one substituted or unsubstituted carbazolyl group.

[0139] In the compound according to this embodiment, ring A 1 , ring B 1 and ring C 1 It is preferable that at least one of the rings has at least one substituted or unsubstituted N-carbazolyl group.

[0140] In the compound according to this embodiment, ring C 1 However, it is preferable that the compound has at least one substituted or unsubstituted carbazolyl group.

[0141] In the compound according to this embodiment, ring C 1 However, it is preferable that the compound has at least one substituted or unsubstituted N-carbazolyl group.

[0142] In the compound according to this embodiment, ring A 1 , ring B 1 and ring C 1 Preferably, at least one of the rings has a group represented by the following general formula (10).

[0143] [ka]

[0144] (In the above general formula (10), R 151 ~R 158 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, -O-(R 190 ) a base represented by -S-(R 191 ) a base represented by 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, -C(=O)-O-(R 192 ) a base represented by -C(=O)-N(R 193 )(R 194 ) a base represented by -N(R 195 )(R 196 ) a base represented by Nitro group, and -Si(R 197 )(R 198 )(R 199 Selected from a group consisting of the groups represented by ), L 11 teeth, 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, m is 0, 1, 2, or 3. When m is 0, the nitrogen atom N of the carbazole ring represented by general formula (10) * is ring A 1, ring B 1 or ring C 1 It is directly coupled with, When m is 2 or 3, multiple L 11 They are either identical or different from one another. ** is ring A 1 , ring B 1 or ring C 1 (This indicates the bonding position.)

[0145] In the compound according to this embodiment, ring A 1 , ring B 1 and ring C 1 The substituted or unsubstituted N-carbazolyl group of at least one of the above is the group represented by the general formula (10) in ring A 1 , ring B 1 and ring C 1 It is also preferable for them to bond.

[0146] In the compound according to this embodiment, it is preferable that m in the general formula (10) is 0 or 1.

[0147] In the compound according to this embodiment, at least one cyano group is ring B 1 It is preferable to substitute with .

[0148] In the compound according to this embodiment, ring B 1 and ring C 1 However, it is preferable that each ring is independently represented by one of the following general formulas (1-1) to (1-5).

[0149] [ka]

[0150] (In the above general formula (1-1), n ​​is 0, 1, 2, 3, 4, 5, or 6, In the above general formulas (1-4), R 121 teeth, 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, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Selected from the group consisting of heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, In the above general formulas (1-5), R 122 and R 123 The combinations of these are single bonds, -O-, -S-, >C(R 112 )(R 113 ), >Si(R 114 )(R 115 ), via a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 122 and R 123 Each of them operates independently. hydrogen atom, halogen 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, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Selected from the group consisting of heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, The rings represented by the general formulas (1-1) to (1-5) may have further substituents or be unsubstituted, provided that ring B 1 and ring C 1 At least one of them is substituted with a cyano group.

[0151] In the compound according to this embodiment, R 112 ~R 115 These are, respectively, R in the general formula (1) above. 112 ~R 115It is synonymous with [the above].

[0152] The six-membered ring shown in the above general formulas (1-1) to (1-5) is ring B 1 or ring C 1 It is preferable that it condenses into the structure represented by the general formula (1) above.

[0153] In the compound according to this embodiment, ring B 1 and ring C 1 However, it is also preferable that each ring is independently represented by the general formula (1-1) mentioned above.

[0154] In the compound according to this embodiment, it is preferable that n in the general formula (1-1) is 0.

[0155] In the compound according to this embodiment, the ring represented by the general formula (1-1) is preferably the ring represented by the formula (1-1A).

[0156] In the compound according to this embodiment, ring B 1 and ring C 1 However, it is also preferable that each ring is independently represented by the above formula (1-1A).

[0157] In the compound according to this embodiment, ring B 1 and ring C 1 One of them is a ring represented by the general formula (1-1), and ring B 1 and ring C 1 It is also preferable that the other part is a ring represented by the general formulas (1-2), (1-3), (1-4), or (1-5).

[0158] In the compound according to this embodiment, ring B 1 and ring C 1 One of them is a ring represented by the general formula (1-1), and ring B 1 and ring C 1 It is also preferable that the other part is a ring represented by either the general formula (1-2) or (1-3).

[0159] In the compound according to this embodiment, ring A 1 It is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, even more preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms, and even more preferably a substituted or unsubstituted benzene ring.

[0160] The compound according to this embodiment may also be represented by the following general formula (11).

[0161] [ka]

[0162] (In the above general formula (11), R 101 ~R 111 and L 1 These are, respectively, R in the general formula (1) above. 101 ~R 111 and L 1 It is synonymous with, R 131 ~R 140 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, -O-(R 190 ) a base represented by -S-(R 191 ) a base represented by 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, -C(=O)-O-(R 192 ) a base represented by -C(=O)-N(R 193 )(R 194 ) a base represented by -N(R 195 )(R 196 ) a base represented by Nitro group, and -Si(R 197 )(R 198 )(R 199 Selected from a group consisting of the groups represented by ), R 134 ~R 140 At least one of them is a cyano group.

[0163] The compound according to this embodiment may also be represented by the following general formula (111).

[0164] [ka]

[0165] (In the above general formula (111), R 101 ~R 111 These are, respectively, R in the general formula (1) above. 101 ~R 111 It is synonymous with, R 131 ~R 140 These are, respectively, R in the general formula (11) above. 134 ~R 140 (This is synonymous with...)

[0166] In the compound according to this embodiment, R 131 ~R 140 Preferably, at least one of them is a substituted or unsubstituted carbazolyl group, and more preferably a substituted or unsubstituted N-carbazolyl group.

[0167] In the compound according to this embodiment, R 134 ~R 137Preferably, at least one of them is a substituted or unsubstituted carbazolyl group, and more preferably a substituted or unsubstituted N-carbazolyl group.

[0168] In the compound according to this embodiment, R 134 ~R 140 Preferably, at least one of them is a cyano group, R 138 ~R 140 It is more preferable that at least one of them is a cyano group.

[0169] The compound according to this embodiment may also be represented by the following general formula (12).

[0170] [ka]

[0171] (In the above general formula (12), R 101 ~R 111 and L 1 These are, respectively, R in the general formula (1) above. 101 ~R 111 and L 1 It is synonymous with, X 1 is -O-, -S-, >N(R 121 ) or >C(R 122 )(R 123 ) and R 121 R in the above general formula (1-4) is 121 It is synonymous with, R 122 and R 123 These are, respectively, R in the general formulas (1-5) above. 122 and R 123 It is synonymous with, R 161 ~R 172 Each of them operates independently. hydrogen atom, halogen atom, Cyano group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, -O-(R 190 ) a base represented by -S-(R 191 ) a base represented by 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, -C(=O)-O-(R 192 ) a base represented by -C(=O)-N(R 193 )(R 194 ) a base represented by -N(R 195 )(R 196 ) a base represented by Nitro group, and -Si(R 197 )(R 198 )(R 199 Selected from a group consisting of the groups represented by ), R 164 ~R 172 At least one of them is a cyano group.

[0172] The compound according to this embodiment may also be represented by the following general formula (121).

[0173] [ka]

[0174] (In the above general formula (121), R 101 ~R 111 These are, respectively, R in the general formula (1) above. 101 ~R 111 It is synonymous with, X 1 and R 161 ~R 172These are, respectively, X in the general formula (12) above. 1 and R 161 ~R 172 (This is synonymous with...)

[0175] In the compound according to this embodiment, R 101 ~R 109 and R 111 Preferably, it is a hydrogen atom.

[0176] In this specification, a cycloalkenyl group having 3 to 50 ring-forming carbon atoms means a monovalent monocyclic group having 3 to 50 ring-forming carbon atoms, having at least one double bond within the ring, but lacking aromaticity. Unless otherwise specified herein, the number of ring-forming carbon atoms in the cycloalkenyl group is 3 to 50, preferably 3 to 20, and more preferably 3 to 6. Specific examples of the cycloalkenyl group described herein include, for example, a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0177] In this specification, a ring-forming cycloalkenylene group having 3 to 50 carbon atoms is a divalent group derived by removing one hydrogen atom from the cycloalkene ring of a ring-forming cycloalkenyl group having 3 to 50 carbon atoms. Specific examples of ring-forming cycloalkenylene groups having 3 to 50 carbon atoms include divalent groups derived by removing one hydrogen atom from the cycloalkene ring of a specific example of a ring-forming cycloalkenyl group having 3 to 50 carbon atoms.

[0178] In the compound according to this embodiment, the substituent ("any substituent") in the phrase "substituted or unsubstituted" is: 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, Unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R902 )(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, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and It is preferable that the group be selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring-forming atoms. In the compound according to this embodiment, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are 2 or more of them, then there are 2 or more R 901 They are either identical or different from each other. R 902 If there are 2 or more of them, then there are 2 or more R 902 They are either identical or different from each other. R 903 If there are 2 or more of them, then there are 2 or more R 903 They are either identical or different from each other. R 904 If there are 2 or more of them, then there are 2 or more R 904 They are either identical or different from each other. R 905 If there are 2 or more of them, then there are 2 or more R 905 They are either identical or different from each other. R 906 If there are 2 or more of them, then there are 2 or more R 906 They are either identical or different from each other. R907 If there are 2 or more of them, then there are 2 or more R 907 They are either identical or different from one another.

[0179] In one embodiment, the substituent referred to as "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 50 carbon atoms, aryl groups having 6 to 50 ring-forming carbon atoms, and heterocyclic groups having 5 to 50 ring-forming atoms.

[0180] In one embodiment, the substituent referred to as "substituted or unsubstituted" is a group selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, aryl groups having 6 to 18 ring-forming carbon atoms, and heterocyclic groups having 5 to 18 ring-forming atoms.

[0181] In the compounds according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0182] In the phrase "substituted or unsubstituted," "unsubstituted" means that hydrogen atoms are bonded.

[0183] (Method for producing the first compound) The compound according to this embodiment (the first compound) can be produced according to the synthesis method described in the examples below, or by following that synthesis method and using known alternative reactions and raw materials suited to the target product.

[0184] (Specific example of the first compound) Specific examples of the compound according to this embodiment (the first compound) include, for example, the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is denoted as D in the chemical formula, and a light hydrogen atom is denoted as H or omitted from the description. In this specification, a methyl group may be denoted as Me, and a phenyl group as Ph.

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[0255] (Maximum peak wavelength) The maximum peak wavelength of the compound according to the first embodiment (a compound having the structure represented by the general formula (1)) is preferably 500 nm or more and 560 nm or less, preferably 500 nm or more and 550 nm or less, and more preferably 515 nm or more and 540 nm or less. In the organic EL element of the third embodiment, the compound having the structure represented by the general formula (1) preferably exhibits green emission. In this specification, green emission means emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 500 nm to 560 nm.

[0256] In this specification, the method for measuring the maximum peak wavelength of a compound is as follows: -6 mol / L or more, 10 -5Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. At room temperature (300K), measure the emission spectrum of this sample (toluene solution) using a spectrofluorometer (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using, for example, a spectrofluorometer manufactured by Hitachi High-Tech Science Corporation (device name: F-7000). 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 peak wavelength of fluorescence emission. The emission spectrum half-width (FWHM) is the full width at half maximum at the maximum peak of the emission spectrum.

[0257] [Second Embodiment] [Light-emitting element material] The light-emitting element material according to this embodiment contains the compound according to the first embodiment. The light-emitting element material refers to a material used in any layer of a light-emitting element. One embodiment is a light-emitting element material containing only the compound according to the first embodiment, and another embodiment is a light-emitting element material containing the compound according to the first embodiment and a compound different from the compound in the first embodiment. In the light-emitting element material of this embodiment, it is preferable that the compound according to the first embodiment (the compound represented by the general formula (1)) is a dopant material. In this case, the light-emitting element material may include the compound according to the first embodiment as a dopant material and other compounds such as a host material.

[0258] [Third Embodiment] [Organic electroluminescent element] In this embodiment, an organic EL element will be described as a light-emitting element. The organic EL element according to this embodiment includes a cathode, an anode, and an organic layer contained between the cathode and the anode. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating multiple layers composed of organic compounds. The organic layer may further contain an inorganic compound. At least one layer of the organic layer contains the compound according to the first embodiment (the first compound).

[0259] In other words, one embodiment of the organic EL element according to this embodiment includes a cathode, an anode, and an organic layer contained between the cathode and the anode, wherein at least one layer of the organic layer contains the compound according to the first embodiment as the first compound.

[0260] The organic layer may consist of, for example, a single light-emitting layer, or it may include layers that can be used in an organic EL device. The layers that can be used in an organic EL device are not particularly limited, but examples include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.

[0261] 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 light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in that order, starting from the anode 3 side.

[0262] (Emitting layer) In the organic EL element according to this embodiment, the organic layer includes a light-emitting layer, and it is preferable that the light-emitting layer includes the compound according to the first embodiment (the first compound).

[0263] In the organic EL element according to this embodiment, it is also preferable that the light-emitting layer further includes a delayed fluorescence light-emitting material.

[0264] In the organic EL element according to this embodiment, the light-emitting layer preferably contains a first compound and a second compound. The first compound in the light-emitting layer is preferably the compound according to the first embodiment. In this embodiment, the second compound is preferably a host material (sometimes referred to as a matrix material), and the first compound is also preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material). In this specification, "host material" refers to a material that makes up, for example, "50% by mass or more of the layer." Therefore, for example, the light-emitting layer contains the second compound in an amount of 50% by mass or more of the total mass of the light-emitting layer. Alternatively, for example, the "host material" may make up 60% by mass or more of the layer, 70% by mass or more of the layer, 80% by mass or more of the layer, 90% by mass or more of the layer, or 95% by mass or more of the layer.

[0265] When the organic EL element of this embodiment is made to emit light, it is preferable that the compound according to the first embodiment, as the first compound, is mainly emitted in the light-emitting layer.

[0266] In one embodiment, the light-emitting layer may contain a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, it is preferable that the light-emitting layer does not contain phosphorescent material (dopant material). Furthermore, in one embodiment, it is preferable that the luminescent layer does not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0267] In this embodiment, when the light-emitting layer contains the compound according to the first embodiment, it is preferable that the light-emitting layer does not contain phosphorescent metal complexes, and also preferably does not contain metal complexes other than phosphorescent metal complexes.

[0268] (First compound) In the organic EL element according to this embodiment, the first compound is preferably the compound according to the first embodiment. In one embodiment, the first compound is a fluorescent compound that does not exhibit delayed fluorescence.

[0269] (Second compound) In the organic EL element according to this embodiment, the second compound is not particularly limited, but it is preferable that the second compound is a delayed fluorescence emitting material.

[0270] In the organic EL element of this embodiment, it is preferable that the delayed fluorescence emitting material, as the second compound, is a host material. In the organic EL element of this embodiment, it is preferable that the delayed fluorescence emitting material as the second compound is the host material, and the compound according to the first embodiment as the first compound is the dopant material.

[0271] (Delayed fluorescence) Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). In that document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is described. 13 It is explained that if the threshold can be reduced, the reverse energy transfer from the excited triplet state to the excited singlet state, which normally has a low transition probability, can occur with high efficiency, resulting in the expression of thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence generation is explained in Figure 10.38 of the aforementioned document. In this embodiment, the delayed fluorescent luminescent material is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0272] Generally, delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

[0273] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurement is a technique in which a sample is excited by irradiating it with a pulsed laser, and the decay behavior (transient characteristics) of the PL emission after the irradiation is stopped is measured. PL emission in TADF materials is classified into a emission component from singlet excitons generated by the initial PL excitation and a emission component from singlet excitons generated via triplet excitons. The lifetime of the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it originates from singlet excitons generated via long-lived triplet excitons. Thus, there is a significant time difference between the emission from singlet excitons generated by the initial PL excitation and the emission from singlet excitons generated via triplet excitons. Therefore, the emission intensity originating from delayed fluorescence can be determined.

[0274] Figure 2 shows a schematic diagram of an exemplary apparatus for measuring transient PL. An example of a transient PL measurement method using Figure 2, and an example of delayed fluorescence behavior analysis, will be explained.

[0275] The transient PL measurement device 100 shown in Figure 2 comprises a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for housing the measurement sample, a spectrometer 103 for spectrally analyzing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in Figure 2.

[0276] The sample to be placed in sample chamber 102 is obtained by depositing a thin film on a quartz substrate in which a doping material is doped with a matrix material at a concentration of 12% by mass.

[0277] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material. The emitted light is extracted at a 90-degree angle to the direction of the excitation light irradiation, and the extracted light is spectrally analyzed by the spectrometer 103 to form a two-dimensional image in the streak camera 104. As a result, a two-dimensional image is obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to emission intensity. By cropping this two-dimensional image along a predetermined time axis, an emission spectrum is obtained in which the vertical axis is emission intensity and the horizontal axis is wavelength. Furthermore, by cropping this two-dimensional image along the wavelength axis, a decay curve (transient PL) is obtained in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is time.

[0278] For example, thin film sample A was prepared as described above using compound HX1 as the matrix material and compound DX1 as the doping material, and transient PL measurements were performed.

[0279] [ka]

[0280] Here, the decay curves were analyzed using the thin film samples A and B described above. Thin film sample B was prepared using compound HX2 as the matrix material and compound DX1 as the doping material, as described above.

[0281] Figure 3 shows the decay curves obtained from transient PL measurements for thin film sample A and thin film sample B.

[0282] [ka]

[0283] As described above, transient PL measurement allows us to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, we can estimate the fluorescence intensity ratio between fluorescence emitted from a singlet excited state generated by photoexcitation and delayed fluorescence emitted from a singlet excited state generated by reverse energy transfer via a triplet excited state. In materials exhibiting delayed fluorescence, the ratio of the intensity of the slowly decaying delayed fluorescence to the intensity of the rapidly decaying fluorescence is relatively large.

[0284] Specifically, there are two types of emission from delayed-fluorescence materials: prompt emission and delayed emission. Prompt emission is emission observed immediately after the delayed-fluorescence material is excited by pulsed light (light emitted from a pulsed laser) at a wavelength absorbed by the material. Delayed emission is emission that is not observed immediately after excitation by the pulsed light, but is observed later.

[0285] The amounts and ratios of prompt emission and delayed emission can be determined using a method similar to that described in “Nature 492, 234-238, 2012” (Reference 1). The apparatus used to calculate the amounts of prompt emission and delayed emission is not limited to the apparatus described in Reference 1 or the apparatus shown in Figure 2.

[0286] Furthermore, in this specification, the delayed fluorescence of delayed fluorescence luminescent materials is measured using samples prepared by the following method. For example, the delayed fluorescence luminescent material is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength in order to remove the contribution of self-absorption. In addition, to prevent quenching by oxygen, the sample solution is frozen and degassed, then sealed in a lidded cell under an argon atmosphere to obtain an argon-saturated, oxygen-free sample solution. The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra and equation (1) in Morris et al. J.Phys.Chem.80(1976)969.

[0287] In this embodiment, the amount of prompt emission (immediate emission) of the compound to be measured (delayed fluorescence emission material) is X P Let X be the amount of delayed emission. D When X D / X P It is preferable that the value of is 0.05 or greater. The measurement of the amount and ratio of Prompt emission and Delay emission of compounds other than delayed fluorescence emission materials in this specification is the same as the measurement of the amount and ratio of Prompt emission and Delay emission of delayed fluorescence emission materials.

[0288] (ΔST) In this embodiment, the lowest excitation singlet energy S1 and the energy gap T at 77[K] are used. 77K The difference between (S1-T) 77K Define ) as ΔST.

[0289] The lowest excitation singlet energy S1(M2) of a delayed fluorescence material and the energy gap T at 77[K] of the delayed fluorescence material. 77K The difference ΔST(M2) from (M2) is preferably less than 0.3eV, more preferably less than 0.2eV, even more preferably less than 0.1eV, and even more preferably less than 0.01eV. That is, ΔST(M2) preferably satisfies the relationship of the following formulas (Equation 10), (Equation 11), (Equation 12), or (Equation 13). ΔST(M2)=S1(M2)-T 77K (M2)<0.3eV…(Number 10) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV …(Math. 11) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV …(Math. 12) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV …(Math. 13)

[0290] (Relationship between triplet energy and the energy gap at 77 K) Here, we will explain the relationship between triplet energy and the energy gap at 77[K]. In this embodiment, the energy gap at 77[K] differs from the triplet energy as it is normally defined. The triplet energy is measured as follows: First, a sample is prepared by dissolving the compound to be measured in a suitable solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum of this sample is measured at a low temperature (77 K) (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength). A tangent line is drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from the wavelength value at the intersection of the tangent line and the horizontal axis using a predetermined conversion formula. Here, among the compounds according to this embodiment, the thermally activated delayed fluorescence compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77[K]), and excited singlet states and excited triplet states coexist. As a result, the spectrum measured in the same manner as above includes emission from both excited singlet states and excited triplet states, and it is difficult to distinguish which state emitted the light, but basically the triplet energy value is considered to be dominant. Therefore, in this embodiment, although the measurement method is the same as that for the usual triplet energy T, in order to distinguish that it is different in a strict sense, the value measured as follows is the energy gap T 77KThis method is called [method name]. The compound to be measured is dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is placed in a quartz cell to be used as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample is measured at a low temperature (77 [K]), and a tangent line is drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent line and the horizontal axis is measured. edge Based on [nm], the energy amount calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K Let's assume that. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0291] The tangent to the rise of the phosphorescence spectrum on the short-wavelength side is drawn as follows: When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum (i.e., the tangent at the inflection point) is considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurement, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer can be used. However, the measuring apparatus is not limited to this; measurements may also be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light-receiving device.

[0292] (Lowest excitation singlet energy S1) The following methods can be used to measure the lowest excited singlet energy S1 using a solution (sometimes referred to as the solution method). A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell. The absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long-wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge Examples of absorption spectrum measuring devices include, but are not limited to, Hitachi's spectrophotometer (device name: U3310).

[0293] The tangent to the falling edge of an absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangents at each point on the spectral curve as we move along the spectral curve in the longer wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the value of the slope is minimized on the longest wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the falling edge of the absorption spectrum on the longer wavelength side. Note that maximum absorbance values ​​of 0.2 or less are not included in the maximum value at the longest wavelength mentioned above.

[0294] (Relationship between the first and second compounds in the light-emitting layer) In the organic EL element of this embodiment, when the light-emitting layer includes a compound according to the first embodiment (first compound) and a delayed fluorescence light-emitting material, it is preferable that the lowest excited singlet energy S1(M1) of the first compound (compound according to the first embodiment) and the lowest excited singlet energy S1(M2) of the second compound (delayed fluorescence light-emitting material) satisfy the following equation (Equation 1). S1(M2)>S1(M1)…(Math 1)

[0295] Energy gap T of the first compound at 77[K] 77K(M1) is the energy gap T of the second compound at 77[K]. 77K It is preferable that it be smaller than (M2). That is, it is preferable that the relationship shown in the following formula (Equation 3) is satisfied. T 77K (M2)>T 77K (M1) …(Math 3)

[0296] (Compounds represented by general formula (101)) In this embodiment, the delayed fluorescence luminescence material as the second compound is not particularly limited as long as it is a compound that exhibits delayed fluorescence. In one embodiment, the delayed fluorescence luminescence material as the second compound is a compound represented by the following general formula (20).

[0297] [ka]

[0298] (In the above general formula (20), D X is a group represented by the following general formula (21), general formula (22), or general formula (23), wherein at least one D X This is a group represented by the following general formula (22) or general formula (23), m is 1, 2, 3, or 4, and when m is 2, 3, or 4, multiple D X They are either identical or different from each other. R is independent of each other. hydrogen atom, halogen atom, Substituted or unsubstituted ring-forming aryl groups with 6 to 14 carbon atoms, A heterocyclic group with 5 to 14 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups with 1 to 6 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 6 carbon atoms, -Si(R 291 )(R 292 )(R 293 ) a base represented by -O-(R 294 ) a base represented by -S-(R 295 A base represented by ) or -N(R 296 )(R 297 ) a base represented by n is 0, 1, 2, or 3. When n is 2 or 3, multiple Rs are either identical or different from one another, and the sum of n and m is 4.

[0299] [ka]

[0300] (One or more sets of two or more adjacent R1 to R8 in the general formula (21) above, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formula (22), R 11 ~R 18 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formula (23), R 111 ~R 118 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R1 to R8, R, which do not form the aforementioned substituted or unsubstituted monorings and do not form the aforementioned substituted or unsubstituted condensed rings. 11 ~R 18 and R 111 ~R 118 Each of them operates independently. hydrogen atom, halogen atom, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R 291 )(R 292 )(R 293 ) a base represented by -O-(R 294 ) a base represented by -S-(R 295 A base represented by ) or -N(R 296 )(R 297 It is a base represented by ), In the above general formulas (22) and (23), A2, B2, and C2 are each independently one of the ring structures selected from the group consisting of ring structures represented by the following general formulas (24), (25), and (26): These ring structures A2, B2, and C2 condense with adjacent ring structures at arbitrary positions. p, px, and py are each independently 1, 2, 3, or 4. When p is 2, 3, or 4, the multiple ring structures A2 are either identical or different from one another. When px is 2, 3, or 4, the multiple ring structures B2 are either identical or different from one another. If py is 2, 3, or 4, then multiple ring structures C2 are either identical or different from one another. However, at least one D X This is a group represented by general formula (22) in which p is 2, 3 or 4, and ring structure A2 includes any ring structure selected from the group consisting of ring structures represented by general formulas (25) and (26) below, or a group represented by general formula (23) in which at least one of px and py is 2, 3 or 4, and ring structure B2 or ring structure C2 includes any ring structure selected from the group consisting of ring structures represented by general formulas (25) and (26) below, The asterisks (*) in general formulas (21), (22), and (23) indicate the bonding position with the benzene ring in general formula (20).

[0301] [ka]

[0302] (In the above general formula (24), R 19 and R 20 One or more of the groups consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formulas (25) and (26), X 10 and X 20 Each of them operates independently, NR 120 , a sulfur atom, or an oxygen atom, R 120 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 19 and R 20 Each of them operates independently. hydrogen atom, halogen atom, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R 291 )(R 292 )(R 293 ) a base represented by -O-(R 294 ) a base represented by -S-(R 295 A base represented by ) or -N(R 296 )(R 297 It is a base represented by ).

[0303] (In the second compound, R 291 ~R 297 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0304] In the second compound, R 291 If multiple R 291 They are either identical or different from each other, R 292 If multiple R 292 They are either identical or different from each other, R 293 If multiple R 293 They are either identical or different from each other, R 294 If multiple R 294 They are either identical or different from each other, R 295 If multiple R 295 They are either identical or different from each other, R 296 If multiple R 296 They are either identical or different from each other, R 297 If multiple R 297 They are either identical or different from one another.

[0305] In the compound represented by the general formula (20), the benzene ring of the general formula (20) to which the groups represented by the general formulas (21), (22), and (23) are bonded is the benzene ring explicitly shown in the general formula (20), and R and D X It is not a benzene ring contained within it.

[0306] In the compound represented by the general formula (20), it is also preferable that at least one R is a substituent rather than a hydrogen atom or a halogen atom, and that at least one substituent R is bonded to the benzene ring in the general formula (20) by a carbon-carbon bond.

[0307] In the compound represented by the general formula (20), it is preferable that the sum of the number of substituents R and the number of groups represented by the general formula (22) or general formula (23) is 3 or 4.

[0308] In the general formula (20) described above, R is preferably independently a hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring-forming atoms, a substituted or unsubstituted heteroaryl group having 5 to 14 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 ring-forming atoms. In the above general formulas (21), (22), and (23), R1 to R8, R 11 ~R 18 , and R 111 ~R 118 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. In the above general formula (22), p is preferably 2, 3, or 4. In the general formula (23) above, px and py are preferably 2, 3, or 4, independently of each other.

[0309] (Method for manufacturing delayed-fluorescence luminescent materials) Delayed fluorescence luminescence materials can be manufactured by known methods. Furthermore, delayed fluorescence luminescence materials can also be manufactured by following known methods and using known alternative reactions and raw materials tailored to the target material.

[0310] (Specific examples of delayed fluorescence luminescence materials) Specific examples of delayed-fluorescence materials include the following compounds. However, the present invention is not limited to these specific examples of delayed-fluorescence materials.

[0311] [ka]

[0312] [ka]

[0313] (TADF mechanism) Figure 4 shows an example of the relationship between the energy levels of the second compound M2 when it is a delayed-fluorescence luminescent material and the first compound M1 when it is the compound of the first embodiment in the luminescent layer. In Figure 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound M1. T1(M1) represents the lowest excited triplet state of the first compound M1. S1(M2) represents the lowest excited singlet state of the second compound M2. T1(M2) represents the lowest excited triplet state of the second compound M2. The dashed arrow in Figure 4, pointing from S1(M2) to S1(M1), represents the Förster-type energy transfer from the lowest excited singlet state of the second compound M2 to the first compound M1. As shown in Figure 4, when a compound with a small ΔST(M2) (a delayed fluorescence emission material) is used as the second compound M2, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound M2 to the first compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound M1 can be observed. It is believed that by utilizing this delayed fluorescence due to the TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0314] The second compound used as the host material may be a compound with a higher lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the first compound used as the dopant material. Examples of host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; (3) condensed aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives; (4) condensed heterocyclic compounds such as carbazole derivatives; and (5) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0315] (Emission of organic EL elements) When the organic EL element of this embodiment is made to emit light, it is preferable that the light-emitting layer mainly emits light from a fluorescent compound.

[0316] The organic EL element of this embodiment preferably emits green light. When the organic EL element of this embodiment emits green light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.

[0317] The maximum peak wavelength of light emitted from an organic EL element is measured as follows. Current density is 10 mA / cm² 2 The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage is applied to the element in such a manner. The peak wavelength of the emission spectrum with the maximum emission intensity is measured from the obtained spectral radiance spectrum and defined as the maximum peak wavelength (unit: nm).

[0318] (film thickness of the light-emitting layer) The thickness of the light-emitting layer in the organic EL element of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. When the thickness of the light-emitting layer is 5 nm or more, it is easier to form the light-emitting layer and adjust the chromaticity. When the thickness of the light-emitting layer is 50 nm or less, it is easier to suppress the rise in the driving voltage.

[0319] (Compound content in the luminescent layer) In the organic EL element of this embodiment, the content of the first compound and the second compound contained in the light-emitting layer is preferably within the following ranges, for example. The content of the first compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The upper limit of the total content of the first compound and the second compound in the light-emitting layer is 100% by mass. This embodiment does not exclude the inclusion of materials other than the first compound and the second compound in the light-emitting layer. The light-emitting layer may contain only one type of the first compound, or two or more types. The light-emitting layer may contain only one type of the second compound, or two or more types.

[0320] Let's further explain the configuration of the organic EL element.

[0321] (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.

[0322] (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). 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. 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. Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.

[0323] When the organic EL element is of the bottom emission type, the anode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. In this specification, light-transmitting or semi-transparent means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metallic material having light-transmitting or semi-transparent properties can be appropriately selected from the materials listed in the anode section.

[0324] When the organic EL element is of the top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a light-reflecting metallic material. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-reflecting metallic material can be appropriately selected and used from the materials listed in the anode section. The anode may consist only of a reflective layer, or it may have a multilayer structure comprising a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is positioned between the reflective layer and the hole transport band. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0325] (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. 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. 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.

[0326] When the organic EL element is of the bottom emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed from a metallic material that has light-reflecting properties. The metallic material with light-reflecting properties can be appropriately selected from the materials listed in the cathode section.

[0327] When the organic EL element is of the top-emission type, the cathode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. The light-transmitting or semi-transparent metallic material can be appropriately selected from the materials listed in the cathode section.

[0328] The organic EL element according to this embodiment may be a bottom-emission type organic EL element. Alternatively, the organic EL element according to this embodiment may be a top-emission type organic EL element. When the organic EL element is of the bottom emission type, it is preferable that the anode is a light-transmitting electrode and the cathode is a light-reflecting electrode. When the organic EL element is of the top-emission type, it is preferable that the anode is a light-reflecting electrode with light-reflecting properties and the cathode is a light-transmitting electrode with light-transmitting properties.

[0329] (Capping layer) When an organic EL element is of the top-emission type, the organic EL element usually has a capping layer above the cathode. The capping layer may contain at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). Alternatively, the capping layer may contain at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. Furthermore, a laminate in which layers containing these materials are stacked can also be used as a capping layer.

[0330] (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. 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), 1, Aromatic amine compounds such as 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (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. 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.

[0331] (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 with a hole mobility of / Vs or greater. The hole transport layer may use carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, other materials may be used as long as they have higher hole transport capabilities than electron transport. The layer containing the material with high hole transport capabilities may be a single layer or a layer consisting of two or more layers made of the above materials stacked together.

[0332] (electron transport layer) 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 (abbreviated 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. The substances described here are mainly 10 -6 cm 2 The material has an electron mobility of 1 / Vs or higher. 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 be a single layer or a layer consisting of two or more layers of the above material stacked together. 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.

[0333] (electron injection layer) The electron injection layer is a layer containing a material with high electron injection properties. 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 alkali metals, alkaline earth metals, or compounds thereof in an electron-transporting material, specifically a material containing magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material consisting of 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 with excellent electron transport properties; specifically, for example, the materials that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. Any substance that exhibits electron-donating properties towards organic compounds can be used as the electron donor. 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.

[0334] (Layer formation method) The method for forming each layer of the organic EL element in this embodiment is not limited to those specifically mentioned above, but known methods such as dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet deposition can be employed.

[0335] (film thickness) The film thickness of each organic layer in the organic EL element of this embodiment is not limited to those specifically mentioned above. However, generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if it is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a range of a few nanometers to 1 μm is usually preferred.

[0336] According to this embodiment, since at least one layer of the organic layer contains the compound of the first embodiment, a high-performance organic EL element is realized. According to one embodiment, an organic EL element that emits light with high efficiency and long lifespan is realized. The organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0337] [Fourth Embodiment] [Organic electroluminescent element] The configuration of the organic EL element according to the fourth embodiment will now be described. In the description of the fourth embodiment, components identical to those in the third embodiment will be given the same reference numerals and names, and their descriptions will be omitted or simplified. Furthermore, in the fourth embodiment, materials and compounds not specifically mentioned can be the same as those described in the third embodiment.

[0338] The organic EL element according to the fourth embodiment differs from the organic EL element according to the third embodiment in that the light-emitting layer further contains a third compound. In other respects, it is the same as the third embodiment.

[0339] In the fourth embodiment, the light-emitting layer preferably comprises a first compound, a second compound, and a third compound. In this embodiment, the first compound is more preferably the compound of the first embodiment, and the second compound is even more preferably a delayed fluorescence light-emitting material. In this embodiment, the first compound is preferably a dopant material, and the second compound is preferably a host material. Furthermore, the third compound is preferably not a dopant material. For example, the light-emitting layer of the fourth embodiment may contain the second compound and the third compound in total amounts of 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the total mass of the light-emitting layer.

[0340] (The third compound) In the organic EL element according to this embodiment, the third compound may be a delayed-fluorescence compound or a compound that does not exhibit delayed fluorescence, but it is preferable that it is a compound that does not exhibit delayed fluorescence. The third compound is not particularly limited, but it is preferable that it is a compound other than an amine compound. That is, it is preferable that the third compound does not contain substituted or unsubstituted amino groups. For example, the third compound can be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.

[0341] (Compounds represented by the general formula (3X)) In the organic EL element according to this embodiment, the third compound is also preferably a compound represented by the following general formula (3X).

[0342] [ka]

[0343] (In the above general formula (3X), A3 is 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. L3 is single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, Divalent heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, or A divalent group formed by the bonding of three groups selected from the group consisting of substituted or unsubstituted ring-forming arylene groups with 6 to 30 carbon atoms and substituted or unsubstituted divalent heterocyclic groups with 5 to 30 ring-forming atoms. R 31 ~R 38 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R 38 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 908 A base represented by -COOR 909 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a base represented by -Ge(R 933 )(R 934 )(R 935 ) a base represented by -B(R 936 )(R 937 ) a base represented by 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 (3A).

[0344] [ka]

[0345] (In the above general formula (3A), R B teeth, 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 908 A base represented by -COOR 909 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 ) a base represented by -Ge(R 933 )(R 934 )(R 935 ) a base represented by -B(R 936 )(R 937 ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R B When there are multiple R B They are either identical or different from one another. L 31 teeth, single bond, Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, trivalent groups, tetravalent groups, pentavalent groups or hexavalent groups derived from said arylene groups, A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from said heterocyclic group, or A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, and a trivalent, tetravalent, pentavalent, or hexavalent group derived from said divalent group. L 32 teeth, single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, n3 is 1, 2, 3, 4, or 5. L 31 If it is a single bond, then n3 is 1, and L 32 This is bonded to the carbon atoms of the six-membered ring in the general formula (3X), L 32 When there are multiple L 32 They are either identical or different from one another. * represents the bonding site with the carbon atom of the six-membered ring in the general formula (3X) above.

[0346] (In the third compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 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. R904 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 908 If multiple R 908 They are either identical or different from one another. R 909 If multiple R 909 They are either identical or different from one another. R 931 If multiple R 931 They are either identical or different from one another. R 932 If multiple R 932 They are either identical or different from one another. R 933 If multiple R 933 They are either identical or different from one another. R 934 If multiple R 934 They are either identical or different from one another. R 935 If multiple R 935 They are either identical or different from one another. R 936 If multiple R 936 They are either identical or different from one another. R 937 If multiple R 937 They are either identical or different to one another.

[0347] In the organic EL element according to this embodiment, the third compound is also preferably a compound represented by any of the following general formulas (31) to (36).

[0348] [ka]

[0349] [ka]

[0350] [ka]

[0351] (In the above general formulas (31) to (36), A3 and L3 are equivalent to A3 and L3 in the general formula (3X) above, respectively. R 341 ~R 350 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, X 31 It consists of a sulfur atom, an oxygen atom, and NR 352 or CR 353 R 354 And, R 353 and R 354 A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 341 ~R 350 And, R 352R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 353 and R 354 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, and does not form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0352] In the third compound, R 352 teeth, 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 It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0353] In the third compound, R 353 and R 354 A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 353 and R 354 Each of them operates independently. 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 It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0354] In the third compound, X 31 It is preferable that this atom is a sulfur atom or an oxygen atom.

[0355] In the third compound, A3 is preferably a group represented by any of the following general formulas (A31) to (A37).

[0356] [ka]

[0357] [ka]

[0358] (In the above general formulas (A31) to (A37), Multiple R 300 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 300 , and R 333 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 It is synonymous with, In the general formulas (A31) to (A37) above, the asterisks (*) indicate the bonding position of the third compound with L3, respectively.

[0359] In the third compound, A3 is also preferably a group represented by the general formula (A34), (A35), or (A37).

[0360] The third compound may also preferably be a compound represented by any of the following general formulas (311) to (316).

[0361] [ka]

[0362] [ka]

[0363] [ka]

[0364] [ka]

[0365] [ka]

[0366] [ka]

[0367] (In the above general formulas (311) to (316), L3 is synonymous with L3 in the general formula (3X) above, Multiple R 300 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R 341 ~R 350 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 300 Furthermore, R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. 341 ~R 350 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R38 (This is synonymous with...)

[0368] The third compound may also preferably be a compound represented by the following general formula (321).

[0369] [ka]

[0370] (In the above general formula (321), L3 is synonymous with L3 in the general formula (3X) above, R 31 ~R 38 , and R 301 ~R 308 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0371] In the third compound, L3 is preferably a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms.

[0372] In the third compound, L3 is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0373] In the third compound, L3 is preferably a group represented by the following general formula (317).

[0374] [ka]

[0375] (In the above general formula (317), R 310 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38This is synonymous with *, and each * independently indicates a binding position.

[0376] In the third compound, L3 may also preferably contain a divalent group represented by the following general formula (318) or general formula (319). In the third compound, L3 is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0377] The third compound may also preferably be a compound represented by the following general formula (322) or general formula (323).

[0378] [ka]

[0379] [ka]

[0380] (In the above general formulas (322) and (323), L 31 teeth, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, A substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms, or A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms. However, L 31 It includes a divalent group represented by the following general formula (318) or general formula (319), R 31 ~R 38 , R 300 , and R 321 ~R 328 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0381] [ka]

[0382] (In the above general formula (319), Multiple R 304 Two adjacent pairs of these combine to form a ring represented by the general formula (320), In the above general formula (320), 1* and 2* are each independently of R 304 This shows the bond position with the ring to which it is bonded. In the above general formula (318), R 302 , R in the general formula (319) 303 , R in the general formula (319) 303 , R that does not form a ring represented by the general formula (320) 304 , and R in the general formula (320) 305 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 It is synonymous with, In the general formulas (318) to (320) above, * indicates the bond position, respectively.

[0383] In the third compound, L3 or L 31 The group represented by the general formula (319) is, for example, the group represented by the following general formula (319A).

[0384] [ka]

[0385] (In the above general formula (319A), R 303 , R 304 and R 305 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38This is synonymous with the above general formula (319A), where * indicates the bond position.

[0386] The third compound is the compound represented by the general formula (322), L 31 It is also preferable that the group is represented by the general formula (318).

[0387] The third compound may also preferably be a compound represented by the following general formula (324).

[0388] [ka]

[0389] (In the above general formula (324), R 31 ~R 38 , R 300 , and R 302 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0390] R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R 38 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, 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 (3A) above, In the above general formula (3A), R B teeth, 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 It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0391] R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R 38 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or The group is represented by the general formula (3A) above, In the above general formula (3A), R B It is preferable that the ring-forming aryl group has 6 to 50 carbon atoms and is either substituted or unsubstituted.

[0392] R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R 38 Each of them operates independently. hydrogen atom, A substituted or unsubstituted phenyl group, The group is represented by the general formula (3A) above, In the above general formula (3A), R B It is preferable that this is a substituted or unsubstituted phenyl group.

[0393] The third compound is also preferably a compound that does not have a pyridine ring, a pyrimidine ring, or a triazine ring.

[0394] (Method for producing the third compound) The third compound can be produced by known methods. Alternatively, the third compound can also be produced by following known methods and using known alternative reactions and starting materials tailored to the target compound.

[0395] (Specific examples of the third compound) Specific examples of the third compound according to this embodiment are shown below. However, the third compound in the present invention is not limited to these specific examples.

[0396] [ka]

[0397]

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[0398]

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[0402]

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[0404]

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[0405]

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[0406]

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[0407]

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[0408]

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[0409]

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[0410]

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[0411]

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[0412]

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[0418] [ka]

[0419] [ka]

[0420] [ka]

[0421] (Relationship between the first compound, the second compound, and the third compound in the light-emitting layer) In the organic EL element of this embodiment, when the light-emitting layer includes a second compound and a third compound, it is preferable that the lowest excited singlet energy S1(M2) of the second compound and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship shown in the following formula (Equation 2). S1(M3)>S1(M2)…(Math 2)

[0422] Energy gap T at 77[K] of the third compound 77K (M3) is the energy gap T of the first compound at 77[K]. 77K It is preferable that it be greater than (M1). Energy gap T at 77[K] of the third compound 77K (M3) is the energy gap T of the second compound at 77[K]. 77K It is preferable that it be greater than (M2).

[0423] It is preferable that the lowest excited singlet energy S1(M1) of the first compound, the lowest excited singlet energy S1(M2) of the second compound, and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship shown in the following formula (Equation 2A). S1(M3)>S1(M2)>S1(M1)…(Number 2A)

[0424] Energy gap T of the first compound at 77[K]77K (M1) and the energy gap T at 77[K] of the second compound 77K (M2) and the energy gap T of the third compound at 77[K] 77K (M3) preferably satisfies the relationship shown in the following formula (Mathematics 2B). T 77K (M3)>T 77K (M2)>T 77K (M1) …(Math 2B)

[0425] (Compound content in the luminescent layer) In the organic EL element of this embodiment, if the light-emitting layer contains a first compound, a second compound, and a third compound, the content of the first compound, the second compound, and the third compound in the light-emitting layer is preferably within the following ranges, for example. In the organic EL element of this embodiment, the content of the first compound in the light-emitting layer is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of the third compound is preferably 10% by mass or more and 80% by mass or less. The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100% by mass. This embodiment does not exclude the possibility that the light-emitting layer may contain materials other than the first compound, the second compound, and the third compound. The light-emitting layer may contain only one type of the first compound, or two or more types. The light-emitting layer may contain only one type of the second compound, or two or more types. The light-emitting layer may contain only one type of the third compound, or two or more types.

[0426] (Emission of organic EL elements) When the organic EL element of this embodiment is made to emit light, it is preferable that the compound of the first embodiment is mainly emitted in the light-emitting layer. When the organic EL element of this embodiment is made to emit light, it is preferable that the light-emitting layer mainly emits light from a fluorescent compound.

[0427] The organic EL element of this embodiment preferably emits green light, similar to the organic EL element of the third embodiment. The maximum peak wavelength of the light emitted from the organic EL element can be measured in the same way as the organic EL element of the third embodiment.

[0428] (TADF mechanism) Figure 5 shows an example of the relationship between the energy levels of the first compound M1, the second compound M2, and the third compound M3 in the light-emitting layer. In Figure 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound M1, and T1(M1) represents the lowest excited triplet state of the first compound M1. S1(M2) represents the lowest excited singlet state of the second compound M2, and T1(M2) represents the lowest excited triplet state of the second compound M2. S1(M3) represents the lowest excited singlet state of the third compound M3, and T1(M3) represents the lowest excited triplet state of the third compound M3. The dashed arrow from S1(M2) to S1(M1) in Figure 5 represents the Förster-type energy transfer from the lowest excited singlet state of the second compound M2 to the first compound M1. As shown in Figure 5, when a compound with a small ΔST(M2) (a delayed fluorescence material) is used as the second compound M2, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound M2 to the first compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound M1 can be observed. It is believed that by utilizing this delayed fluorescence due to the TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0429] According to this embodiment, since at least one layer of the organic layer contains the compound of the first embodiment, a high-performance organic EL element is realized. According to one embodiment, an organic EL element that emits light with high efficiency and long lifespan is realized. The organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0430] [Fifth 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.

[0431] [Changes to 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.

[0432] For example, the light-emitting layer is not limited to one layer, but may consist of multiple light-emitting layers stacked together. When an organic EL element has multiple light-emitting layers, it is sufficient that at least one organic layer satisfies the conditions described in the above embodiment, and it is preferable that at least one light-emitting layer contains the compound of the first embodiment. When one of the multiple light-emitting layers contains the compound of the first 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. 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.

[0433] Alternatively, for example, a barrier layer may be provided adjacent to at least one of the anode and cathode sides of the light-emitting layer. The barrier layer is preferably positioned in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, if a barrier layer is placed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching the layer on the cathode side of the barrier layer (e.g., the electron transport layer). If the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer. Furthermore, if a barrier layer is placed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching the layer on the anode side of the barrier layer (for example, a hole transport layer). If the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light-emitting layer and the hole transport layer. Furthermore, a barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to the surrounding layers. This prevents excitons generated in the light-emitting layer from moving to layers closer to the electrodes than the barrier layer (for example, electron transport layers and hole transport layers). It is preferable that the light-emitting layer and the barrier layer are bonded together.

[0434] 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]

[0435] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.

[0436] <Compound> The compounds having the structure represented by general formula (1) used in the manufacture of the organic EL elements in Examples 1 to 3 are shown below.

[0437] [ka]

[0438] The comparative compounds used in the manufacture of the organic EL element related to Comparative Example 1 are shown below.

[0439] [ka]

[0440] Other compounds used in the manufacture of the organic EL elements in Examples 1-3 and Comparative Example 1 are listed below.

[0441] [ka]

[0442] <Fabrication of Organic EL Devices> Organic EL elements were fabricated and evaluated as follows.

[0443] (Example 1) A glass substrate with a 25mm x 75mm x 1.1mm thick ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130 nm. The glass substrate with the transparent electrode line, after cleaning, was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT-1 and compound HA were co-deposited onto the surface on which the transparent electrode line was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The proportion of compound HT-1 in the hole injection layer was 97% by mass, and the proportion of compound HA was 3% by mass. Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 90 nm. Next, compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 30 nm. Next, compound HOST, acting as a host material (third compound), compound TADF, acting as a delayed fluorescence emission material (second compound), and compound GD-A, acting as a fluorescence emission material (first compound), were co-deposited onto the second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The proportion of compound HOST in the light-emitting layer was set to 74.2% by mass, the proportion of compound TADF to 25% by mass, and the proportion of compound GD-A to 0.8% by mass. Next, compound ET-1 was deposited onto the light-emitting layer to form a hole barrier layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited onto the hole barrier layer to form an electron transport layer with a thickness of 50 nm. The proportion of compound ET-2 in the electron transport layer was set to 50% by mass, and the proportion of Liq was set to 50% by mass. Next, ytterbium (Yb) was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was deposited onto the electron injection layer to form a metallic Al cathode with a thickness of 80 nm. As described above, an organic EL element according to Example 1 was fabricated. The element configuration of the organic EL element according to Example 1 is schematically shown below. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(90) / HT-2(30) / HOST:TADF:GD-A(25,74.2%:25%:0.8%) / ET-1(5) / ET-2:Liq(50,50%:50%) / Yb(1) / Al(80) In the above device configuration, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the above device configuration, the percentages in parentheses (97%:3%) indicate the proportion (mass%) of compound HT-1 and compound HA in the hole injection layer, the percentages (74.2%:25%:0.8%) indicate the proportion (mass%) of compound HOST, compound TADF, and compound GD-A in the light-emitting layer, and the percentages (50%:50%) indicate the proportion (mass%) of compound ET-2 and Liq in the electron transport layer.

[0444] (Examples 2 and 3) The organic EL elements of Example 2 and Example 3 were fabricated in the same manner as the organic EL element of Example 1, except that the compound GD-A in the light-emitting layer of the organic EL element of Example 1 was replaced with the first compound listed in Table 1.

[0445] (Comparative Example 1) The organic EL element of Comparative Example 1 was fabricated in the same manner as the organic EL element of Example 1, except that the compound GD-A in the light-emitting layer of the organic EL element of Example 1 was replaced with the first compound listed in Table 1.

[0446] <Evaluation of Organic EL Devices> The fabricated organic EL elements were evaluated as follows. The evaluation results are shown in Table 1. The singlet energies S1 of the first, second, and third compounds used in the light-emitting layer of each example are also shown in Table 1.

[0447] (Drive voltage) A current density of 10 mA / cm² is applied between the anode and cathode of the fabricated organic EL element. 2 The voltage (in volts) was measured when the power was applied in such a manner. Based on the measured drive voltage for each example, and the following formula (Equation 1X), the "drive voltage (relative value)" (unit: %) was calculated. Drive voltage (relative value) = (Drive voltage of each example / Drive voltage of comparative example 1) × 100 ... (Equation 1 x)

[0448] (CIE1931 chromaticity) The fabricated organic EL element has a current density of 10 mA / cm². 2 The CIE1931 chromaticity coordinates (x, y) were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to achieve the above result.

[0449] (Maximum peak wavelength λ when the element is driven) EL (and emission half-width FWHM) The fabricated organic EL element has a current density of 10 mA / cm². 2The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied in such a manner. From the obtained spectral radiance spectrum, the maximum peak wavelength λ was determined. EL The emission width at half maximum (FWHM) was calculated (in nm). FWHM is an abbreviation for full width at half maximum.

[0450] (External quantum efficiency EQE) The fabricated organic EL element has a current density of 10 mA / cm². 2 The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied in such a manner. From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that lambassian emission occurred. Based on the measured values ​​of EQE for each example, and the following formula (Equation 2X), "EQE95 (relative value)" (unit: %) was calculated. EQE (relative value) = (EQE of each example / EQE of comparison example 1) × 100 ... (Math 2X)

[0451] (Life span LT95) Current density is 50 mA / cm² 2 A voltage was applied to an organic EL element fabricated to achieve the desired result, and the time it took for the brightness to reach 95% of the initial brightness (LT95 (unit: hours)) was measured as the lifetime. Brightness was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Based on the measured values ​​of LT95 for each example, and the following formula (Equation 3X), the "LT95 (relative value)" (unit: %) was calculated. LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100 ... (Math 3X)

[0452] [Table 1]

[0453] As shown in Table 1, the organic EL elements of Examples 1 to 3, which include compounds GD-A, GD-B, or GD-C as compounds having the structure represented by general formula (1), emitted light with higher efficiency and longer lifespan compared to the organic EL element of Comparative Example 1, which used comparative compound Ref-1.

[0454] <Evaluation of Compounds> The following evaluations were performed on the compounds used in the fabrication of the organic EL elements.

[0455] (Delayed fluorescence) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 2. The compound TADF was dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength was prepared to eliminate the contribution of self-absorption. Furthermore, to prevent quenching by oxygen, the sample solution was freeze-degassed and then sealed in a lidded cell under an argon atmosphere to obtain an argon-saturated, oxygen-free sample solution. The fluorescence spectra of the above sample solutions were measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield was calculated using equation (1) in Morris et al. J.Phys.Chem.80(1976)969. After the compound TADF is excited by pulsed light (light irradiated from a pulsed laser) at a wavelength absorbed by the compound, there are two types of emission: Prompt emission (immediate emission) which is observed immediately from the excited state, and Delay emission (delayed emission) which is not observed immediately after excitation but is observed later. In this embodiment, delayed fluorescence emission means that the amount of Delay emission (delayed emission) is 5% or more of the amount of Prompt emission (immediate emission). Specifically, the amount of Prompt emission (immediate emission) is X P Let X be the amount of delayed emission. D When X D / X P This means the value is 0.05 or greater. The amounts and ratios of prompt emission and delayed emission can be determined using a method similar to that described in “Nature 492, 234-238, 2012” (Reference 1). The apparatus used to calculate the amounts of prompt emission and delayed emission is not limited to the apparatus described in Reference 1 or the apparatus shown in Figure 2. For the compound TADF, it was confirmed that the amount of delayed emission was 5% or more of the amount of prompt emission. Specifically, regarding the compound TADF, X D / X P The value was 0.05 or higher.

[0456] (Lowest excitation singlet energy S1) The singlet energy S1 was measured using the solution method described above.

[0457] <Example of synthesis> (Synthesis of intermediate A1)

[0458] [ka]

[0459] Under a nitrogen atmosphere, 1-bromo-4-t-butyl-2-nitrobenzene (110 g, 427 mmol), 1-pyreneboronic acid (100 g, 406 mmol), tetrakis(triphenylphosphine)palladium(0) (14.1 g, 12.2 mmol), sodium carbonate (86 g, 813 mmol), 1,2-dimethoxyethane (900 mL), and deionized water (450 mL) were placed in a three-necked flask and heated, stirred, and refluxed for 4 hours. After the reaction mixture was cooled to room temperature, the precipitated solid was filtered off. The obtained solid was purified by silica gel column chromatography to obtain 122 g of an orange solid. Mass spectrometry identified the orange solid as intermediate A1 (yield 79%).

[0460] (Synthesis of intermediate A2)

[0461] [ka]

[0462] Under a nitrogen atmosphere, intermediate A1 (50 g, 143 mmol), triphenylphosphine (94 g, 358 mmol), and orthodichlorobenzene (286 mL) were placed in a three-necked flask and stirred at 180°C for 10 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by recrystallization to obtain 39.3 g of a white solid. Mass spectrometry identified the white solid as intermediate A2 (yield 79%).

[0463] (Synthesis of intermediate A3)

[0464] [ka]

[0465] Under a nitrogen atmosphere, intermediate A2 (95 g, 273 mmol), 1-bromo-2,6-difluorobenzene (185 g, 957 mmol), tripotassium phosphate (290 g, 1367 mmol), and N,N-dimethylformamide (1367 mL) were placed in a three-necked flask and stirred at 100°C for 10 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The obtained solid was purified by silica gel column chromatography to obtain 82.7 g of a yellow solid. Mass spectrometry identified the yellow solid as intermediate A3 (yield 58%).

[0466] (Synthesis of intermediate A4)

[0467] [ka]

[0468] Under a nitrogen atmosphere, 4-chloro-2-iodonitrobenzene (70 g, 247 mmol), 4-(9H-carbazole-9-yl)phenylboronic acid (71 g, 247 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (4.0 g, 4.95 mmol), tripotassium phosphate (115 g, 544 mmol), 1,4-dioxane (500 mL), and deionized water (250 mL) were placed in a three-necked flask and stirred at room temperature for 4 hours. After the reaction mixture was cooled to room temperature, the organic layer was extracted using a separatory funnel. The extracted organic layer was concentrated and purified by silica gel column chromatography to obtain 93 g of a yellow solid. Mass spectrometry identified the yellow solid as intermediate A4 (yield 94%).

[0469] (Synthesis of intermediate A5)

[0470] [ka]

[0471] Under a nitrogen atmosphere, intermediate A4 (93 g, 233 mmol), triphenylphosphine (153 g, 582.7 mmol), and orthodichlorobenzene (ODCB) (500 mL) were placed in a three-necked flask and heated, stirred, and refluxed for 12 hours. The reaction mixture was concentrated and purified by silica gel column chromatography to obtain 42 g of a white solid. Mass spectrometry identified the white solid as intermediate A5 (yield 49%).

[0472] (Synthesis of intermediate A6)

[0473] [ka]

[0474] Under a nitrogen atmosphere, intermediate A3 (50 g, 96 mmol), intermediate A5 (4.36 g, 98 mmol), tripotassium phosphate (102 g, 481 mmol), and N,N-dimethylformamide (DMF) (200 mL) were placed in a three-necked flask and stirred at 100°C for 12 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The obtained solid was purified by silica gel column chromatography to obtain 73 g of a pale yellow solid. Mass spectrometry identified the pale yellow solid as intermediate A6 (yield 88%).

[0475] (Synthesis of intermediate A7)

[0476] [ka]

[0477] Under a nitrogen atmosphere, intermediate A6 (73 g, 84 mmol) and t-butylbenzene (842 mL) were placed in a three-necked flask and cooled to -40°C. Then, sec-butyllithium solution (solvent: cyclohexane and n-hexane), 1.2 mol / L (140 mL, 168 mmol) was added dropwise, and the mixture was stirred for 2 hours. After cooling the reaction mixture to -70°C, boron tribromide (24 mL, 253 mmol) was added dropwise, and the mixture was heated to room temperature and stirred for 2 hours. After cooling the reaction mixture to 0°C, N,N-diisopropylethylamine (117 mL, 674 mmol) was added dropwise, and the mixture was heated to 130°C and stirred for 3 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration to obtain 44 g of an orange solid. Mass spectrometry identified the orange solid as intermediate A7 (yield 66%).

[0478] (Synthesis of compound GD-A)

[0479] [ka]

[0480] Under a nitrogen atmosphere, intermediate A7 (2.4 g, 3.0 mmol), potassium hexacyanoferrate(II) (2.2 g, 6.0 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphin]palladium(II) (0.21 g, 0.30 mmol), sodium carbonate (0.06 g, 0.6 mmol), and 1-methyl-2-pyrrolidone (60 mL) were placed in a three-necked flask and stirred at 135 °C for 4 hours. The reaction mixture was cooled to room temperature, 60 mL of dichloromethane and silica gel were added, and the mixture was filtered by suction. The resulting solution was concentrated, methanol was added, and the resulting solid was purified by silica gel column chromatography to obtain 1.1 g of an orange solid. Mass spectrometry identified the orange solid as compound GD-A (yield 46%).

[0481] (Synthesis of intermediates B1 and B2)

[0482] [ka]

[0483] Under a nitrogen atmosphere, 2-4-dichloroaniline (40.0 g, 247 mmol), 4-bromodibenzofuran (61.0 g, 247 mmol), tris(dibenzylideneacetone)dipalladium(0) (4.52 g, 4.94 mmol), (±)-2,2'-bis(diphenylphosphin)-1,1'-binaphthyl (6.15 g, 9.88 mmol), sodium t-butoxide (35.6 g, 370 mmol), and toluene (823 mL) were placed in a three-necked flask and stirred at 100°C for 5 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 58.3 g of a white solid. Mass spectrometry identified the white solid as intermediate B1 (yield 66%). Under a nitrogen atmosphere, intermediate B1 (24.1 g, 73.4 mmol), palladium(II) acetate (0.66 g, 2.94 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (2.45 g, 5.87 mmol), potassium carbonate (22.3 g, 162 mmol), and N,N-dimethylacetamide (245 mL) were placed in a three-necked flask and stirred at 150 °C for 12 hours. After the reaction mixture was cooled to room temperature, water and toluene were added and the mixture was separated. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 3.7 g of a white solid. Mass spectrometry identified the white solid as intermediate B2 (yield 17%).

[0484] (Synthesis of intermediate B3)

[0485] [ka]

[0486] Under a nitrogen atmosphere, intermediate A3 (7.50 g, 14.4 mmol), intermediate B2 (4.20 g, 14.4 mmol), tripotassium phosphate (9.20 g, 43.2 mmol), and N,N-dimethylformamide (36.0 mL) were placed in a three-necked flask and stirred at 140°C for 21 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The obtained solid was purified by silica gel column chromatography to obtain 1.95 g of a pale yellow solid. Mass spectrometry identified the pale yellow solid as intermediate B3 (yield 17%).

[0487] (Synthesis of intermediate B4)

[0488] [ka]

[0489] Under a nitrogen atmosphere, intermediate B3 (1.95 g, 2.50 mmol) and t-butylbenzene (25 mL) were placed in a three-necked flask and cooled to -60°C. Then, s-butyllithium solution (solvent: cyclohexane and n-hexane), 1.2 mol / L (4.10 mL, 4.90 mmol) was added dropwise, and the temperature was raised to -40°C and stirred for 30 minutes. After cooling the reaction mixture to -78°C, boron tribromide (0.70 mL, 7.40 mmol) was added dropwise, and the temperature was raised to room temperature and stirred for 10 hours. After cooling the reaction mixture to 0°C, N,N-diisopropylethylamine (2.90 mL, 17.2 mmol) was added dropwise, and the temperature was raised to 130°C and stirred for 2 hours. After cooling the reaction mixture to room temperature, the precipitated solid was collected by suction filtration and purified by recrystallization to obtain 1.00 g of orange solid. Mass spectrometry identified the orange solid as intermediate B4 (yield 56%).

[0490] (Synthesis of compound GD-B)

[0491] [ka]

[0492] Under a nitrogen atmosphere, intermediate B4 (1.00 g, 1.40 mmol), potassium hexacyanoferrate(II) (1.00 g, 2.80 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphin]palladium(II) (0.20 g, 0.30 mmol), sodium carbonate (0.12 g, 1.40 mmol), and 1-methyl-2-pyrrolidone (28 mL) were placed in a three-necked flask and stirred at 135°C for 5 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration and purified by recrystallization to obtain 0.25 g of an orange solid. Mass spectrometry identified the orange solid as compound GD-B (yield 25%).

[0493] (Synthesis of intermediates C1, C2, and C3)

[0494] [ka]

[0495] Under a nitrogen atmosphere, 1-bromo-3-fluoro-2-nitrobenzene (80.3 g, 365 mmol), phenylboronic acid (46.7 g, 383 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane adduct (8.94 g, 10.9 mmol), 1,4-dioxane (912 mL), and water (456 mL) were placed in a three-necked flask and stirred at 80°C for 1 hour. After the reaction mixture was cooled to room temperature, ethyl acetate was added and the mixture was separated. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 71.2 g of a yellow solid. Mass spectrometry identified the yellow solid as intermediate C1 (yield 90%).

[0496] Under a nitrogen atmosphere, intermediate C1 (70.2 g, 323 mmol), 2-bromo-3-chlorophenol (73.7 g, 356 mmol), potassium carbonate (134 g, 970 mmol), and N,N-dimethylformamide (808 mL) were placed in a three-necked flask and stirred at 100 °C for 18 hours. After the reaction mixture was cooled to room temperature, palladium(II) acetate (3.63 g, 16.2 mmol) and triphenylphosphine (8.48 g, 32.3 mmol) were added, and the temperature was raised to 130 °C and stirred for 2 hours. The reaction mixture was cooled to room temperature, water was added, and the precipitated solid was collected by suction filtration. The obtained solid was purified by silica gel column chromatography and recrystallization to obtain 88.2 g of a white solid. Mass spectrometry identified the white solid as intermediate C2 (yield 84%).

[0497] Under a nitrogen atmosphere, intermediate C2 (88.0 g, 272 mmol), triphenylphosphine (178 g, 680 mmol), and orthodichlorobenzene (543 mL) were placed in a three-necked flask and stirred at 180°C for 10 hours. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 54.0 g of a white solid. Mass spectrometry identified the white solid as intermediate C3 (yield 68%).

[0498] (Synthesis of intermediate C4)

[0499] [ka]

[0500] In the synthesis of intermediate B3, the same method was used except that intermediate C3 was used instead of intermediate B2, yielding a yellow solid (4.90 g). Mass spectrometry identified the yellow solid as intermediate C4 (yield 20%).

[0501] (Synthesis of intermediate C5)

[0502] [ka]

[0503] In the synthesis of intermediate B4, the same method was used except that intermediate C4 was used instead of intermediate B3, yielding an orange solid (1.28 g). Mass spectrometry identified the orange solid as intermediate C5 (yield 29%).

[0504] (Synthesis of compound GD-C)

[0505] [ka]

[0506] The synthesis of compound GD-B was carried out using the same method as before, except that intermediate C5 was used instead of intermediate B4, and an orange solid (0.40 g) was obtained. Mass spectrometry identified the orange solid as compound GD-C (yield 31%). [Explanation of Symbols]

[0507] 1...Organic EL element, 2...Substrate, 3...Anode, 4...Cathode, 5...Light-emitting layer, 6...Hole injection layer, 7...Hole transport layer, 8...Electron transport layer, 9...Electron injection layer.

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