Compound, Material for Organic Electroluminescent Element, Organic Electroluminescent Element, and Electronic Device

Abstract

This compound is represented by general formula (1). In general formula (1), X1 is CR1 or a nitrogen atom, X2 is CR2 or a nitrogen atom, X3 is CR3 or a nitrogen atom, X4 is CR4 or a nitrogen atom, X5 is CR5 or a nitrogen atom, X6 is CR6 or a nitrogen atom, X7 is CR7, a nitrogen atom, or a carbon atom bonded to X8 via a single bond, X8 is CR8, a nitrogen atom, or a carbon atom bonded to X7 via a single bond, X9 is CR9 or a nitrogen atom, X10 is CR10 or a nitrogen atom, X11 is CR11 or a nitrogen atom, X12 is CR12 or a nitrogen atom, Q is CRQ or a nitrogen atom, Y is NRY1, an oxygen atom, a sulfur atom, C(RY2)(RY3), or Si(RY4)(RY5), and each R is a hydrogen atom or a substituent.

Description

Technical Field

[0001] The present invention relates to a compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device.

Background Art

[0002] When a voltage is applied to an organic electroluminescence 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 rule of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%. Fluorescent organic EL devices that use light emission from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but the internal quantum efficiency of 25% is said to be the limit. Therefore, studies have been conducted to improve the performance of organic EL devices. Examples of the performance of organic EL devices include luminance, emission wavelength, full width at half maximum, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0003] For example, in addition to singlet excitons, it is expected to use triplet excitons to make the organic EL device emit light more efficiently. Against this background, highly efficient fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and studied. The TADF (Thermally Activated Delayed Fluorescence) mechanism is a mechanism that utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet level and the triplet level is used. Thermally activated delayed fluorescence is described, for example, in "Device Physical Properties of Organic Semiconductors" edited by Chiba Yada, published by Kodansha on April 1, 2012, pages 261-268. As a compound exhibiting thermally activated delayed fluorescence (TADF property) (hereinafter also referred to as a TADF property compound), for example, a compound in which a donor site and an acceptor site are bonded within a molecule is known.

[0004] As a literature regarding an organic EL element and a compound used for an organic EL element, for example, Patent Document 1 can be cited.

Prior Art Document

Patent Document

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] An object of the present invention is to provide a compound capable of improving the performance of an organic EL element, a material for an organic electroluminescence element containing the compound, an organic electroluminescence element containing the compound, and an electronic device equipped with the organic electroluminescence element.

Means for Solving the Problems

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

[0008]

Chemical Formula

[0009] (In the general formula (1), X1 is CR1 or a nitrogen atom, X2 is CR2 or a nitrogen atom, X3 is CR3 or a nitrogen atom, X4 is CR4 or a nitrogen atom, X5 is CR5 or a nitrogen atom, X6 is CR6 or a nitrogen atom, X7 is CR7, a nitrogen atom, or a carbon atom bonded to X8 by a single bond, X8 is CR8, a nitrogen atom, or a carbon atom bonded to X7 by a single bond, X9 is CR9 or a nitrogen atom, X 10 is CR 10 or a nitrogen atom, X 11 is CR 11 or a nitrogen atom, X 12 is CR 12 or a nitrogen atom, Q is CR Q or a nitrogen atom, Y is NR Y1 , an oxygen atom, a sulfur atom, C(R Y2 )(R Y3 ) or Si(R Y4 )(R Y5 ), One or more sets of two or more adjacent ones among R1 to R6 and R9 to R 11 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, One or more sets of two or more adjacent ones among R 3、 R4 and R Y1 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, At least one hydrogen in the monocyclic or condensed ring formed by bonding one or more sets of two or more adjacent ones among R 3、 R4 and R Y1 to each other is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, A heterocyclic group having 5 to 50 ring-forming atoms, -O-(R 920 ) group, and -N(R 921 )(R 922 ) group, or is not substituted, at least one hydrogen in the substituent is substituted or not substituted with an aryl group having 6 to 50 ring-forming carbon atoms or an alkyl group having 1 to 50 carbon atoms, the substituted or unsubstituted single ring is not formed, and the substituted or unsubstituted condensed ring is not formed for R1 to R 11 , and R 12 ~R 13 , and R Q are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group, -O-(R 914 ) group, -S-(R 915 ) group, -N(R 916 )(R 917 ) group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 918 ) group, -COOR 919 ) group, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring Y1 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R Y2 and R Y3 the group consisting of are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring Y2 and R Y3 , and R Y4 and R Y5 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 911 ~R 922 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 911 When there are a plurality of 911 R's, the plurality of R 912 When there are a plurality of 912 R's, the plurality of R 913 When there are a plurality of 913 R's, the plurality of R 914 When there are a plurality of 914 R's, the plurality of R 915 When there are a plurality of 915 R's, the plurality of R 916 When there are a plurality of 916 R's, the plurality of R 917 When there are a plurality of 917 R's, the plurality of R 918 When there are a plurality of 918 R's, the plurality of R 919 When there are a plurality of 919 R's, the plurality of R 920 When there are a plurality of 920 R's, the plurality of R 921 When there are a plurality of 921 R's, the plurality of R 922 When there are a plurality of 922 R's are the same as or different from each other.)

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

[0011] According to one aspect of the present invention, there is provided an organic electroluminescence device having a cathode, an anode, and an organic layer included between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains a compound according to one aspect of the present invention.

[0012] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence device according to one aspect of the present invention.

[0013] According to one aspect of the present invention, a compound capable of improving the performance of an organic EL device can be provided. Further, according to one aspect of the present invention, a material for an organic electroluminescence device containing the compound can be provided. Further, according to one aspect of the present invention, an organic electroluminescence device containing the compound can be provided. Further, according to one aspect of the present invention, an electronic device equipped with the organic electroluminescence device can be provided.

Brief Description of the Drawings

[0014]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Embodiments for Carrying Out the Invention

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

[0016] In this specification, in a chemical structural formula, at a bondable position where symbols such as "R" or "D" representing a deuterium atom are not explicitly shown, it is assumed that a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is bonded.

[0017] In this specification, the number of ring-forming carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed-ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same shall apply to the "number of ring-forming carbon atoms" 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 number of ring-forming carbon atoms of a 9,9-diphenylfluorenyl group is 13, and the number of ring-forming carbon atoms of a 9,9'-spirobifluorenyl group is 25. Also, when, for example, an alkyl group is substituted as a substituent on a benzene ring, the number of carbon atoms of the 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 of a benzene ring substituted with an alkyl group is 6. Also, when, for example, an alkyl group is substituted as a substituent on a naphthalene ring, the number of carbon atoms of the 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 of 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 a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic, condensed ring, and ring assembly) (e.g., monocyclic compound, condensed ring compound, bridged compound, carbocyclic compound, and heterocyclic compound). Atoms that do not form the ring (e.g., hydrogen atoms that terminate the bonds of the atoms forming the ring) and atoms contained in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. Unless otherwise specified, the "number of ring-forming atoms" described below shall be the same. 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 a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. Also, for example, the number of hydrogen atoms bonded to a carbon atom of a quinazoline ring or the number of atoms constituting a substituent is not included in the number of quinazoline ring-forming atoms. Therefore, the number of ring-forming atoms in a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

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

[0020] In this specification, in the expression "substituted or unsubstituted ZZ group having XX to YY atoms", "XX to YY atoms" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of substituents when the ZZ group is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0021] As used herein, an unsubstituted ZZ group refers to the case where the "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to the case where the "substituted or unsubstituted ZZ group" is a "substituted ZZ group". As used herein, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom. Also, as used herein, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by the AA group.

[0022] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.

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

[0024] · "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B), etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is the "substituted aryl group"). In this specification, when simply referring to the "aryl group", it includes both the "unsubstituted aryl group" and the "substituted aryl group". The "substituted aryl group" means a group in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced by substituents. Examples of the "substituted aryl group" include, for example, a group in which one or more hydrogen atoms of the "unsubstituted aryl group" in the following specific example group G1A are replaced by substituents, and examples of the substituted aryl groups in the following specific example group G1B. Note that the examples of the "unsubstituted aryl group" and the "substituted aryl group" listed here are only examples, and the "substituted aryl group" described in this specification includes a group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent.

[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 with substituents.

[0029] ·"Substituted or unsubstituted heterocyclic group" The "heterocyclic group" described in this specification is a cyclic group containing at least one heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom. The "heterocyclic group" described in this specification is a monocyclic group or a condensed ring group. The "heterocyclic group" described in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic groups (specific example group G2A), substituted heterocyclic groups (specific example group G2B), and the like. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, when simply referring to the "heterocyclic group", it includes both the "unsubstituted heterocyclic group" and the "substituted heterocyclic group". The "substituted heterocyclic group" means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of the "substituted heterocyclic group" include groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the following specific example group G2A are replaced, and examples of the substituted heterocyclic groups in the following specific example group G2B. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification also includes groups in which the hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0030] The specific example 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 structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0031] The specific example group G2B includes, for example, a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), a substituted heterocyclic group containing a sulfur atom (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4).

[0032] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): Pyrrolyl group, Imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, Isooxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, Pyrazinyl group, Triazinyl group, Indolyl group, Isoindolyl group, Indolizinyl group, Quinolizinyl group, Quinolyl group, Isoquinolyl group, Cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenanthridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, and a diazacarbazolyl group.

[0033] ·an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzoisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0034] ·an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), Diazaazadibenzothiophenyl group (diazaazadibenzothienyl group), Azananofbenzothiophenyl group (azananofbenzothienyl group), and Diazaazananofbenzothiophenyl group (diazaazananofbenzothienyl group).

[0035] · A monovalent heterocyclic group 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):

[0036]

Chemical formula

[0037]

Chemical formula

[0038] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH, or CH2. However, at least one of X A and Y A is an oxygen atom, a sulfur atom, or NH. In the general formulas (TEMP-16) to (TEMP-33), when at least one of X A and Y A is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0039] · A substituted heterocyclic group containing a nitrogen atom (specific example group G2B1): (9-Phenyl)carbazolyl group, (9-Biphenylyl)carbazolyl group, (9-Phenyl)phenylcarbazolyl group, (9-Naphthyl)carbazolyl group, Diphenylcarbazol-9-yl group, Phenylcarbazol-9-yl group, Methylbenzimidazolyl group, Ethylbenzimidazolyl group, Phenyltriazinyl group, Biphenylyltriazinyl group, Diphenyltriazinyl group, Phenylquinazolinyl group, and biphenylylquinazolinyl group.

[0040] ·Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and Monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene].

[0041] ·Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-Butyldibenzothiophenyl group, and Monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].

[0042] ·A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by the general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (specific example group G2B4):

[0043] Said "one or more hydrogen atoms of the monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, X A and Y A when at least one of them is NH, a hydrogen atom bonded to the nitrogen atom, and X A and Y Ameans one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of them is CH2.

[0044] · "Substituted or unsubstituted alkyl group" Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when simply referred to as "alkyl group", both "unsubstituted alkyl group" and "substituted alkyl group" are included. "Substituted alkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced by substituents. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl groups" (specific example group G3A) are replaced by substituents, and examples of the substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" of the specific example group G3B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "substituted alkyl group" of the specific example group G3B is further replaced by a substituent.

[0045] · Unsubstituted alkyl group (specific example group G3A): Methyl group, Ethyl group, n-Propyl group, Isopropyl group, n-Butyl group, Isobutyl group, s-Butyl group, and t-butyl group.

[0046] · Substituted alkyl group (specific example group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-Trifluoroethyl group, and Trifluoromethyl group.

[0047] · "Substituted or unsubstituted alkenyl group" Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and the "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when simply referring to an "alkenyl group", it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group". The "substituted alkenyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced by substituents. Specific examples of the "substituted alkenyl group" include groups in which the following "unsubstituted alkenyl groups" (specific example group G4A) have substituents, and examples of substituted alkenyl groups (specific example group G4B), etc. Note that the examples of the "unsubstituted alkenyl group" and the "substituted alkenyl group" listed here are only examples, and the "substituted alkenyl group" described in this specification includes groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl group" of specific example group G4B are further replaced by substituents.

[0048] · Unsubstituted alkenyl group (specific example group G4A): Vinyl group, Allyl group, 1-Butenyl group, 2-Butenyl group, and 3-Butenyl group.

[0049] · Alkenyl groups for substitution (specific example group G4B): 1,3 - butadienyl group, 1 - methylvinyl group, 1 - methylallyl group, 1,1 - dimethylallyl group, 2 - methylallyl group, and 1,2 - dimethylallyl group.

[0050] · "Substituted or unsubstituted alkynyl group" Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A), etc. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group"). Hereinafter, when simply referred to as "alkynyl group", it includes both "unsubstituted alkynyl group" and "substituted alkynyl group". The "substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are replaced by substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (specific example group G5A) are replaced by substituents, etc.

[0051] · Unsubstituted alkynyl group (specific example group G5A): Ethynyl group.

[0052] · "Substituted or unsubstituted cycloalkyl group" Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A), substituted cycloalkyl groups (specific example group G6B), and the like. (Here, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when simply referring to the "cycloalkyl group", it includes both the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group". The "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced by substituents. Specific examples of the "substituted cycloalkyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl groups" (specific example group G6A) are replaced by substituents, and examples of the substituted cycloalkyl group (specific example group G6B). It should be noted that the examples of the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group" listed here are only examples, and the "substituted cycloalkyl group" described in this specification includes groups in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of specific example group G6B are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl group" of specific example group G6B are further replaced by substituents.

[0053] · Unsubstituted cycloalkyl groups (specific example group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1 - Adamantyl group, 2 - Adamantyl group, 1 - Norbornyl group, and 2 - Norbornyl group.

[0054] · Substituted cycloalkyl groups (specific example group G6B): 4 - Methylcyclohexyl group.

[0055] · "A group represented by -Si(R 901 )(R 902 )(R 903 )" Examples (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification include -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, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6. The plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other. The plurality of G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The plurality of G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The plurality of G6s in -Si(G6)(G6)(G6) are the same as or different from each other.

[0056] · "A group represented by -O-(R 904 )" -O-(R904 ) Examples of the group represented by (specific example group G8) include -O(G1), -O(G2), -O(G3), and -O(G6) are included. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0057] · The group represented by "-S-(R 905 )" Examples of the group represented by -S-(R 905 ) in this specification (specific example group G9) include -S(G1), -S(G2), -S(G3), and -S(G6) are included. Here, G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

[0058] · The group represented by "-N(R 906 )(R 907 )" Examples of the group represented by -N(R 906 )(R 907 ) in this specification (specific example group G10) include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) may be mentioned. Here, G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2. G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6. The plurality of G1 in -N(G1)(G1) are the same as or different from each other. The plurality of G2 in -N(G2)(G2) are the same as or different from each other. The plurality of G3 in -N(G3)(G3) are the same as or different from each other. The plurality of G6 in -N(G6)(G6) are the same as or different from each other.

[0059] · "halogen atom" Specific examples (specific example group G11) of the "halogen atom" described in this specification include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0060] · "substituted or unsubstituted fluoroalkyl group" As used herein, the term "substituted or unsubstituted fluoroalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is from 1 to 50, preferably from 1 to 30, more preferably from 1 to 18. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms in the "fluoroalkyl group" are replaced by substituents. It should be noted that the "substituted fluoroalkyl group" described herein includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted fluoroalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted fluoroalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted fluoroalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by fluorine atoms, and the like.

[0061] · "substituted or unsubstituted haloalkyl group" As used herein, the term "substituted or unsubstituted haloalkyl group" means a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced by halogen atoms. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted haloalkyl group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced by substituents. In addition, the "substituted haloalkyl group" as described herein includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the "substituted haloalkyl group" are further replaced by substituents, and a group in which one or more hydrogen atoms of the substituents in the "substituted haloalkyl group" are further replaced by substituents. Specific examples of the "unsubstituted haloalkyl group" include examples of groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by halogen atoms. The haloalkyl group may be referred to as a halogenated alkyl group.

[0062] · "Substituted or unsubstituted alkoxy group" Specific examples of the "substituted or unsubstituted alkoxy group" as described herein are groups represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkoxy group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.

[0063] · "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" as described herein are groups represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkylthio group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.

[0064] · "Substituted or unsubstituted aryloxy group" Specific examples of the "substituted or unsubstituted aryloxy group" described in the present specification are groups represented by -O(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 aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0065] · "Substituted or unsubstituted arylthio group" Specific examples of the "substituted or unsubstituted arylthio group" described in the present specification are groups 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 in the present specification.

[0066] · "Substituted or unsubstituted trialkylsilyl group" Specific examples of the "trialkylsilyl group" described in the present specification are groups represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3. A plurality of G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The number of carbon atoms of each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0067] · "Substituted or unsubstituted aralkyl group" Specific examples of the "substituted or unsubstituted aralkyl group" described in this specification include a 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, the "aralkyl group" is a group in which a hydrogen atom of the "alkyl group" is replaced by an "aryl group" as a substituent, and is one aspect of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" 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, etc.

[0068] The substituted or unsubstituted aryl group described in this specification is preferably a 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, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group, etc., unless otherwise specified in this specification.

[0069] The substituted or unsubstituted heterocyclic group described in this specification is preferably a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazol-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyl dibenzothiophenyl group, etc., unless otherwise described in this specification.

[0070] In this specification, the carbazolyl group is specifically any of the following groups unless otherwise described in this specification.

[0071]

Chemical formula

[0072] In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise described in this specification.

[0073]

Chemical formula

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

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

[0076]

Chemical formula

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

[0078] Unless otherwise specified herein, the substituted or unsubstituted alkyl group described in this specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, etc.

[0079] · "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above "substituted or unsubstituted aryl group". Specific examples (specific example group G12) of the "substituted or unsubstituted arylene group" include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1, etc.

[0080] · "Substituted or unsubstituted divalent heterocyclic group" Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom on the heterocyclic ring from the above "substituted or unsubstituted heterocyclic group". Specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" include divalent groups derived by removing one hydrogen atom on the heterocyclic ring from the "substituted or unsubstituted heterocyclic group" described in specific example group G2, etc.

[0081] · "Substituted or unsubstituted alkylene group" Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3, and the like.

[0082] Unless otherwise specified in this specification, the substituted or unsubstituted arylene group described in this specification is preferably a group of any of the following general formulas (TEMP-42) to (TEMP-68).

[0083]

Chemical formula

[0084]

Chemical formula

[0085] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the above general formulas (TEMP-42) to (TEMP-52), * represents the bonding position.

[0086]

Chemical formula

[0087] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. The groups Q9 and Q 10 may be bonded to each other via a single bond to form a ring. In the general formulas (TEMP-53) to (TEMP-62), * represents the bonding position.

[0088]

Chemical formula

[0089] In the general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

[0090] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic group described herein is preferably a group represented by any of the following general formulas (TEMP-69) to (TEMP-102).

[0091]

Chemical formula

[0092]

Chemical formula

[0093]

Chemical formula

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

[0095]

Chemical formula

[0096]

Chemical formula

[0097] [Chemistry]

[0098] [Chemistry]

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

[0100] The above is the description of "the substituents described in this specification".

[0101] · "When bonding to form a ring" In this specification, the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other" means the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring", the case of "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring", and the case of "one or more sets of two or more adjacent ones do not bond to each other". Regarding the case in this specification where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent ones bond to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "the case of bonding to form a ring"), the following will be described. Taking the case of an anthracene compound represented by the following general formula (TEMP-103) whose mother skeleton is an anthracene ring as an example.

[0102] [Chemistry]

[0103] For example, R921 ~R 930 Among them, in the case of "one or more sets consisting of two or more adjacent ones are combined with each other to form a ring", the set consisting of two adjacent ones that forms one set is R 921 and R 922 and the set of R 922 and R 923 and the set of R 923 and R 924 and the set of R 924 and R 930 and the set of R 930 and R 925 and the set of R 925 and R 926 and the set of R 926 and R 927 and the set of R 927 and R 928 and the set of R 928 and R 929 and the set of, and R 929 and R 921 and the set of.

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

[0105]

Chemical formula

[0106] The case where a "set consisting of two or more adjacent ones" forms a ring includes not only the case where a set consisting of "two" adjacent ones is combined as in the above example, but also the case where a set consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form ring Q A , and R 922 and R923 are bonded to each other to form ring Q C to form, and a group consisting of three adjacent ones (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and condensed to the anthracene backbone. In this case, the anthracene compound represented by the 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 share R 922 .

[0107] [Chemical formula]

[0108] The "monocyclic ring" or "condensed ring" formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "a pair consisting of two adjacent ones" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" can form a saturated ring or an unsaturated ring. For example, ring Q A and ring Q B formed in the general formula (TEMP-104) are each a "monocyclic ring" or "condensed ring", respectively. Also, ring Q A and ring Q C formed in the general formula (TEMP-105) are "condensed rings". Ring Q A and ring Q C in the general formula (TEMP-105) are a condensed ring formed by the condensation of ring Q A and ring Q C . If ring Q A in the general formula (TMEP-104) is a benzene ring, ring Q A is a monocyclic ring. If ring Q A in the general formula (TMEP-104) is a naphthalene ring, ring Q A is a condensed ring.

[0109] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the parent skeleton or a plurality of atoms of the parent skeleton and one or more arbitrary elements. For example, in the general formula (TEMP-104), R 921 and R 922 are bonded to each other to form a ring Q A which means a ring formed by a carbon atom of the anthracene skeleton to which R 921 is bonded, a carbon atom of the anthracene skeleton to which R 922 is bonded, and one or more arbitrary elements. Specific examples include, when R 921 and R 922 form a ring Q A , when a single-ring unsaturated ring is formed by a carbon atom of the anthracene skeleton to which R 921 is bonded, a carbon atom of the anthracene skeleton to which R 922 is bonded, and four carbon atoms, the ring formed by R 921 and R 922 is a benzene ring.

[0110] Here, "arbitrary element" is preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element, unless otherwise specified in this specification. In an arbitrary element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated by a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. When an arbitrary element other than the carbon element is included, the formed ring is a heterocyclic ring. Unless otherwise specified herein, the "one or more arbitrary elements" constituting the monocyclic or condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified herein, among the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred. Unless otherwise specified herein, among the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, the "monocyclic ring" 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 groups" "are bonded to each other to form a substituted or unsubstituted monocyclic ring" or "are bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon, nitrogen, oxygen, and sulfur elements.

[0111] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the section of "substituents described in this specification" mentioned above. The above is the explanation for the case where "one or more sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more sets of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" (the case of "bonding to form a ring").

[0112] · Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (which may be referred to as "any substituent" in the present specification) is, for example, An unsubstituted alkyl group having 1 to 50 carbon atoms, An unsubstituted alkenyl group having 2 to 50 carbon atoms, An unsubstituted alkynyl group having 2 to 50 carbon atoms, An unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), A halogen atom, a cyano group, a nitro group, An unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and An unsubstituted heterocyclic group having 5 to 50 ring-forming atoms And groups selected from the group consisting of, Here, R 901 ~R 907 Are each independently, A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. R 901 When two or more R 901 Exist, two or more R R 902 When two or more R 902 Exist, two or more R R 903When there are two or more, two or more Rs 903 are the same as or different from each other, R 904 When there are two or more, two or more Rs 904 are the same as or different from each other, R 905 When there are two or more, two or more Rs 905 are the same as or different from each other, R 906 When there are two or more, two or more Rs 906 are the same as or different from each other, R 907 When there are two or more, two or more Rs 907 are the same as or different from each other.

[0113] In one embodiment, the substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, and a heterocyclic group having 5 to 50 ring-forming atoms is a group selected from the group consisting of.

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

[0115] Specific examples of each group of the above-mentioned arbitrary substituents are the specific examples of the substituents described in the section of "substituents described in this specification" described above.

[0116] Unless otherwise specified herein, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may further have a substituent. The substituents that any substituent may further have are the same as the above-mentioned any substituent.

[0117] As used herein, the numerical range represented by "AA~BB" means a range including the numerical value AA described before "AA~BB" as the lower limit value and the numerical value BB described after "AA~BB" as the upper limit value.

[0118] 〔First Embodiment〕 (Compound)

[0119] The compound according to this embodiment is represented by the following general formula (1). The compound according to this embodiment may sometimes be referred to as the compound represented by the general formula (1).

[0120]

Chemical formula

[0121] (In the general formula (1), X1 is CR1 or a nitrogen atom, X2 is CR2 or a nitrogen atom, X3 is CR3 or a nitrogen atom, X4 is CR4 or a nitrogen atom, X5 is CR5 or a nitrogen atom, X6 is CR6 or a nitrogen atom, X7 is CR7, a nitrogen atom, or a carbon atom bonded to X8 by a single bond, X8 is CR8, a nitrogen atom, or a carbon atom bonded to X7 by a single bond, X9 is CR9 or a nitrogen atom, X 10 is CR 10 or a nitrogen atom, X 11 is CR 11 or a nitrogen atom, X 12 is CR 12 or a nitrogen atom, Q is CR Q or a nitrogen atom, Y is NR Y1 , an oxygen atom, a sulfur atom, C(R Y2 )(R Y3 ) or Si(R Y4 )(R Y5 ), One or more of the sets of two or more adjacent ones of R1 to R6 and R9 to R 11 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, One or more of the sets of two or more adjacent ones of R 3、 R4 and R Y1 are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, At least one hydrogen in the monocyclic ring or condensed ring formed by bonding one or more of the sets of two or more adjacent ones of R 3、 R4 and R Y1 to each other is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, a heterocyclic group having 5 to 50 ring-forming atoms, a group represented by -O-(R 920 ), and -N(R 921 )(R 922) is substituted with at least any substituent selected from the group consisting of the groups represented by, or is not substituted, At least one hydrogen in the substituent is substituted with an aryl group having 6 to 50 ring-forming carbon atoms or an alkyl group having 1 to 50 carbon atoms, or is not substituted, R1 to R that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring 11 , and R 12 ~R 13 , and R Q are each independently A hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 ) group represented by, -O-(R 914 ) group represented by, -S-(R 915 ) group represented by, -N(R 916 )(R 917 ) group represented by, A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 918 ) group represented by, -COOR 919 ) group represented by, A halogen atom, A cyano group, A nitro group, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring Y1 is A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or A substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R Y2 and R Y3 wherein the group consisting of are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other, do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, and R Y2 and R Y3 , and R Y4 and R Y5 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 911 ~R 922 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 911 When a plurality of R 911 are present, the plurality of R R912 When there are a plurality of R's 912 they may be the same as or different from each other, R 913 When there are a plurality of R's 913 they may be the same as or different from each other, R 914 When there are a plurality of R's 914 they may be the same as or different from each other, R 915 When there are a plurality of R's 915 they may be the same as or different from each other, R 916 When there are a plurality of R's 916 they may be the same as or different from each other, R 917 When there are a plurality of R's 917 they may be the same as or different from each other, R 918 When there are a plurality of R's 918 they may be the same as or different from each other, R 919 When there are a plurality of R's 919 they may be the same as or different from each other, R 920 When there are a plurality of R's 920 they may be the same as or different from each other, R 921 When there are a plurality of R's 921 they may be the same as or different from each other, R 922 When there are a plurality of R's 922 they may be the same as or different from each other.)

[0122] In the compound according to this embodiment, when X7 is a carbon atom bonded to X8 by a single bond and X8 is a carbon atom bonded to X7 by a single bond, for example, the general formula (1) is represented by the following general formula (1A).

[0123]

Chemical formula

[0124] (In the general formula (1A), X1 to X6, X9 to X 12 , Y, Q, and R 13 are each independently as defined in the general formula (1).)

[0125] The compound according to this embodiment is preferably represented by the following general formula (2).

[0126] [Chemical formula]

[0127] (In the general formula (2), R1 to R 13 , R Y1 , R Q are each independently as defined in the general formula (1).)

[0128] The compound according to this embodiment is preferably represented by the following general formula (2A).

[0129] [Chemical formula]

[0130] (In the general formula (2A), R1 to R6, R9 to R 13 , R Y1 , R Q are each independently as defined in the general formula (1).)

[0131] The compound according to this embodiment is preferably represented by the following general formula (3).

[0132] [Chemical formula]

[0133] (In the general formula (3), R1 to R3, R5 to R 13 and R QEach is independently as defined by the general formula (1), R x1 ~R x4 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, and R X1 ~R x4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 931 )(R 932 )(R 933 ) group represented by -O-(R 934 ) group represented by -S-(R 935 ) group represented by -N(R 936 )(R 937 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 938 group represented by -COOR 939 group represented by a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 931 ~R939 is, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 931 When a plurality of R's exist, the plurality of R's 931 are the same as or different from each other, R 932 When a plurality of R's exist, the plurality of R's 932 are the same as or different from each other, R 933 When a plurality of R's exist, the plurality of R's 933 are the same as or different from each other, R 934 When a plurality of R's exist, the plurality of R's 934 are the same as or different from each other, R 935 When a plurality of R's exist, the plurality of R's 935 are the same as or different from each other, R 936 When a plurality of R's exist, the plurality of R's 936 are the same as or different from each other, R 937 When a plurality of R's exist, the plurality of R's 937 are the same as or different from each other, R 938 When a plurality of R's exist, the plurality of R's 938 are the same as or different from each other, R 939 When a plurality of R's exist, the plurality of R's 939 are the same as or different from each other.)

[0134] In the general formula (3), for example, the pair consisting of R5 and R6 may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[0135] The compound according to this embodiment is preferably represented by the following general formula (3A).

[0136] [Chemical formula]

[0137] (In the general formula (3A), R1 to R3, R5 to R6, R9 to R 13 and R Q are each independently as defined in the general formula (1), and R x1 to R x4 are each independently as defined in the general formula (3).)

[0138] In the compound according to this embodiment, R1 to R 13 and R Q are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, which is also preferable.

[0139] In the compound according to this embodiment, R1 to R 13 and R Q are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring-forming atoms, which is also preferable.

[0140] In the compound according to this embodiment, R1 to R3, R5 to R 13 , R Q and R x1 to R x4 are each independently a hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms is also preferred.

[0141] In the compound according to this embodiment, R1 to R3, R5 to R 13 , R Q and R x1 ~R x4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring-forming atoms is also preferred.

[0142] In the compound according to this embodiment, R1 to R 13 , R Q and R x1 ~R x4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms is preferred.

[0143] In the compound according to this embodiment, R1 to R 13 , R Q and R x1 ~R x4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring-forming atoms is preferred.

[0144] The compound according to this embodiment is preferably represented by the following general formula (4).

[0145] [Chemical Formula]

[0146] (In the general formula (4), R2, R 6、 R 13、 R Q and R x2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring-forming atoms.)

[0147] The compound according to this embodiment is preferably represented by the following general formula (5).

[0148] [Chemical Formula]

[0149] (In the general formula (5), R2, R 6、 R 13、 R Q and R x2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring-forming atoms.)

[0150] In the compound according to this embodiment, R 13 and R Q are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group is preferred.

[0151] R6 and R x2 are each independently preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0152] In the compound according to this embodiment, when the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 )-represented group, -COOR 909 )-represented group, -S(=O)2R 941 )-represented group, -P(=O)(R 942 )(R 943 )-represented group, -Ge(R 944 )(R 945 )(R 946 )-represented group, a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or A heterocyclic group having 5 to 25 ring-forming atoms without substitution, R 901 ~R 909 and R 941 ~R 946 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms is preferred.

[0153] In the compound according to this embodiment, when the substituent in the case of "substituted or unsubstituted" is a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms is preferred.

[0154] In the compound according to this embodiment, when the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring-forming atoms is preferred.

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

[0156] · Main peak wavelength of the compound The main peak wavelength of the compound according to this embodiment is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, still more preferably 510 nm or more and 530 nm or less. In this specification, the main peak wavelength of a compound means that the compound to be measured is 10 -6 mol / liter or more and 10 -5Refers to the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution dissolved at a concentration of less than or equal to mol / liter. As the measuring device, a spectrofluorophotometer (manufactured by Hitachi, Ltd., F-7000) can be used.

[0157] · Method for producing the compound according to this embodiment The compound according to this embodiment can be produced according to the synthesis method described in the examples below, or by imitating the synthesis method and using known alternative reactions and raw materials adapted to the target product.

[0158] · Specific examples of the compound according to this embodiment Specific examples of the compound according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.

[0159]

Chemical formula

[0160]

Chemical formula

[0161]

Chemical formula

[0162]

Chemical formula

[0163]

Chemical formula

[0164]

Chemical formula

[0165] [Chemistry]

[0166] [Chemistry]

[0167] [Chemistry]

[0168] [Chemistry]

[0169] [Chemistry]

[0170] [Chemistry]

[0171] [Chemistry]

[0172] According to the compound according to this embodiment, the performance of the organic EL element can be improved. According to one embodiment, the driving voltage can be reduced, the EQE can be improved, and light with a narrow full width at half maximum of the main peak can be emitted from the element.

[0173] [Second Embodiment] (Material for Organic Electroluminescence Element) The material for an organic electroluminescence device according to this embodiment contains the compound according to the first embodiment. As one aspect, there is provided a material for an organic electroluminescence device containing only the compound according to the first embodiment. As another aspect, there is provided a material for an organic electroluminescence device containing the compound according to the first embodiment and another compound different from the compound in the first embodiment. In the material for an organic electroluminescence device of this embodiment, it is preferable that the compound according to the first embodiment is a dopant material. In this case, the material for an organic electroluminescence device may contain the compound according to the first embodiment as a dopant material and another compound such as a host material.

[0174] 〔Third Embodiment〕 (Organic Electroluminescence Device) The organic EL device according to this embodiment will be described. The organic EL device according to this embodiment has a cathode, an anode, and an organic layer included 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 a plurality of 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 compound represented by the general formula (1)).

[0175] The organic layer may be composed of, for example, a single light-emitting layer, or may include layers that can be employed in an organic EL device. The layers that can be employed in an organic EL device are not particularly limited, and examples thereof include at least any 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.

[0176] Fig. 1 shows a schematic configuration of an example of the organic EL device according to this embodiment. The organic EL element 1 includes a translucent 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 composed of 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 laminated in this order from the anode 3 side. The present invention is not limited to the configuration of the organic EL element shown in FIG. 1.

[0177] (Light emitting layer) The organic layer of the organic EL element according to the present embodiment includes a light emitting layer. The light emitting layer preferably contains the compound according to the first embodiment (the compound represented by the general formula (1)).

[0178] It is also preferable that the light emitting layer further contains a delayed fluorescence emitting material.

[0179] When the light emitting layer contains the compound according to the first embodiment and the delayed fluorescence emitting material, it is preferable that the lowest excited singlet energy S1(H) of the delayed fluorescence emitting material and the lowest excited singlet energy S1(D) of the compound according to the first embodiment (the compound represented by the general formula (1)) satisfy the following mathematical formula (Formula 1). S1(H)>S1(D)…(Formula 1)

[0180] In the organic EL element according to the present 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 case, 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, an emitter, or a light emitting material). In this specification, the “host material” is, for example, a material contained in “50% by mass or more of the layer”. Therefore, for example, the light emitting layer contains the second compound in 50% by mass or more of the total mass of the light emitting layer. Also, for example, the “host material” may be contained in 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 layer.

[0181] In the organic EL element of the present embodiment, it is preferable that the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M2) of the second compound satisfy the relationship of the following mathematical formula (Formula 3). S1(M2)>S1(M1) …(Formula 3)

[0182] The energy gap T 77K (M1) at 77 [K] of the first compound is preferably smaller than the energy gap T 77K (M2) at 77 [K] of the second compound. That is, it is preferable to satisfy the relationship of the following mathematical formula (Formula 5). T 77K (M2)>T 77K (M1) …(Formula 5)

[0183] When the organic EL element of the present embodiment emits light, it is preferable that in the light-emitting layer, the compound according to the first embodiment as the first compound mainly emits light.

[0184] In one embodiment, the light-emitting layer may contain a metal complex. Also, in one embodiment, it is preferable that the light-emitting layer does not contain a metal complex. Also, in one embodiment, it is preferable that the light-emitting layer does not contain a phosphorescent material (dopant material). Also, in one embodiment, it is preferable that the light-emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of the heavy metal complex include an iridium complex, an osmium complex, and a platinum complex.

[0185] In the present 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 a phosphorescent metal complex, and it is also preferable that the light-emitting layer does not contain a metal complex other than the phosphorescent metal complex.

[0186] (First compound) 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.

[0187] (Second compound) The second compound is not particularly limited, but in the organic EL element of this embodiment, it is preferable that the second compound is a delayed fluorescence emitting material.

[0188] 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 a host material, and the compound according to the first embodiment as the first compound is a dopant material.

[0189] (Delayed fluorescence) Regarding delayed fluorescence, it is explained on pages 261 to 268 of "Device Physical Properties of Organic Semiconductors" (edited by Chiba Ya, published by Kodansha). In that literature, if the energy difference ΔE 13 between the singlet excited state and the triplet excited state of the fluorescent material can be made small, reverse energy transfer from the triplet excited state, which usually has a low transition probability, to the singlet excited state occurs with high efficiency, and it is explained that thermally activated delayed fluorescence (TADF) appears. Furthermore, the generation mechanism of delayed fluorescence is explained in Figure 10.38 in that literature. The delayed fluorescence emitting material in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0190] Generally, the emission of delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0191] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurement. 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. The PL emission in a TADF material is classified into a luminescence component from singlet excitons generated by the first PL excitation and a luminescence component from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds and is very short. Therefore, the emission from the singlet excitons decays rapidly after the pulsed laser irradiation. On the other hand, since delayed fluorescence is the emission from singlet excitons generated via triplet excitons with a long lifetime, it decays slowly. Thus, there is a large temporal difference between the emission from singlet excitons generated by the first PL excitation and the emission from singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be obtained.

[0192] FIG. 2 shows a schematic diagram of an exemplary apparatus for measuring transient PL. A method for measuring transient PL using FIG. 2 and an example of analyzing the behavior of delayed fluorescence will be described.

[0193] The transient PL measurement apparatus 100 in FIG. 2 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for spectroscopically analyzing the light emitted from the measurement sample, a streak camera 104 for imaging 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 apparatus described in FIG. 2.

[0194] The sample accommodated in the sample chamber 102 is obtained by forming a thin film in which a doping material is doped in a matrix material at a concentration of 12% by mass on a quartz substrate.

[0195] A pulse laser is irradiated from the pulse laser unit 101 onto the thin film sample accommodated in the sample chamber 102 to excite the doping material. The emitted light is extracted in a direction 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is dispersed by the spectroscope 103, and a two-dimensional image is formed in the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to the emission intensity. When this two-dimensional image is cut out along a predetermined time axis, an emission spectrum can be obtained in which the vertical axis is the emission intensity and the horizontal axis is the wavelength. Further, when the two-dimensional image is cut out along the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is time.

[0196] For example, as the matrix material, the following reference compound H1 was used, and as the doping material, the following reference compound D1 was used to prepare the thin film sample A as described above, and the transient PL measurement was performed.

[0197]

Chemical formula

[0198] Here, the decay curves were analyzed using the aforementioned thin film sample A and thin film sample B. The thin film sample B was prepared as described above using the following reference compound H2 as the matrix material and the reference compound D1 as the doping material.

[0199] Figure 3 shows the decay curves obtained from the transient PL measured for the thin film sample A and the thin film sample B.

[0200]

Chemical formula

[0201] As described above, by transient PL measurement, a luminescence decay curve can be obtained with the luminescence intensity on the vertical axis and time on the horizontal axis. Based on this luminescence decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated via the triplet excited state by reverse energy transfer can be estimated. In a material with delayed fluorescence properties, the ratio of the intensity of the slowly decaying delayed fluorescence to the intensity of the quickly decaying fluorescence is relatively large to some extent.

[0202] Specifically, as the luminescence from a material with delayed fluorescence properties, there are Prompt luminescence (instantaneous luminescence) and Delay luminescence (delayed luminescence). Prompt luminescence (instantaneous luminescence) is the luminescence immediately observed from the excited state after the material with delayed fluorescence properties is excited by pulsed light (light irradiated from a pulsed laser) with a wavelength absorbed by the material. Delay luminescence (delayed luminescence) is the luminescence that is not immediately observed after excitation by the pulsed light but is observed later.

[0203] The amounts and ratio of Prompt luminescence and Delay luminescence can be determined by a method similar to the method described in "Nature 492, 234 - 238, 2012" (Reference 1). Note that the device used for calculating the amounts of Prompt luminescence and Delay luminescence is not limited to the device described in Reference 1 or the device described in Figure 2.

[0204] Also, in this specification, for measuring the delayed fluorescence property of a delayed fluorescence-emitting material, a sample prepared by the following method is used. For example, the delayed fluorescence-emitting material is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to remove the contribution of self-absorption. Also, to prevent quenching by oxygen, the sample solution is freeze-degassed and then sealed in a cell with a lid under an argon atmosphere to obtain a sample solution saturated with argon and free of oxygen. The fluorescence spectrum of the above sample solution was measured with a spectrofluorophotometer 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 according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0205] In this embodiment, the amount of Prompt emission (prompt fluorescence) of the compound to be measured (delayed fluorescence-emitting material) is X P and the amount of Delay emission (delayed fluorescence) is X D When this is the case, X D / X P is preferably 0.05 or more. The measurement of the amount and ratio of Prompt emission and Delay emission of compounds other than the delayed fluorescence-emitting material in this specification is the same as the measurement of the amount and ratio of Prompt emission and Delay emission of the delayed fluorescence-emitting material.

[0206] ·ΔST In this embodiment, the difference (S1 - T 77K ) between the lowest excited singlet energy S1 and the energy gap T 77K at 77 [K] is defined as ΔST.

[0207] The difference ΔST(H) between the lowest excited singlet energy S1(H) of the delayed fluorescence-emitting material and the energy gap T 77K (H) at 77 [K] of the delayed fluorescence-emitting material is preferably less than 0.3 eV, more preferably less than 0.2 eV, still more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(H) preferably satisfies the relationship of the following mathematical formula (Formula 10), (Formula 11), (Formula 12), or (Formula 13). ΔST(H) = S1(H) - T 77K (H) < 0.3 eV … (Formula 10) ΔST(H) = S1(H) - T 77K (H) < 0.2 eV … (Formula 11) ΔST(H) = S1(H) - T77K (H) < 0.1 eV … (Equation 12) ΔST(H) = S1(H) - T 77K (H) < 0.01 eV … (Equation 13)

[0208] · Relationship between the triplet energy and the energy gap at 77 K Here, the relationship between the triplet energy and the energy gap at 77 K will be described. In this embodiment, the energy gap at 77 K is different from the normally defined triplet energy. The measurement of the triplet energy is performed as follows. First, a sample is prepared by enclosing a solution in which a compound to be measured is dissolved in an appropriate solvent in a quartz glass tube. For this sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 K), a tangent is drawn to the rising edge on the short-wavelength side of this phosphorescence spectrum, and based on the wavelength value at the intersection of the tangent and the horizontal axis, the triplet energy is calculated from a predetermined conversion formula. Here, among the compounds according to this embodiment, the thermally activated delayed fluorescence compounds preferably have a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at a low temperature (77 K), and the excited singlet state and the excited triplet state coexist. As a result, the spectrum measured in the same manner as above includes emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish from which state the emission occurs, but basically, the value of the triplet energy is considered to be dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that it is different in its strict meaning, the value measured as follows is defined as the energy gap T 77KIt is called. The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) so that the concentration becomes 10 μmol / L, and this solution is put into a quartz cell to obtain a measurement sample. For this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]). A tangent line is drawn to the rising edge on the short-wavelength side of this phosphorescence spectrum, and the wavelength value λ edge [nm] Based on this, the energy amount calculated from the following conversion formula (F1) is defined as the energy gap T at 77 [K] 77K . Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[0209] The tangent line to the rising edge on the short-wavelength side of the phosphorescence spectrum is drawn as follows. Starting from the short-wavelength side of the phosphorescence spectrum, when moving along the spectrum curve from the short-wavelength side of the maximum value of the spectrum to the maximum value on the shortest wavelength side, consider the tangent line at each point on the curve towards the long-wavelength side. This tangent line has an increasing slope as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where the value of this slope reaches the maximum value (i.e., the tangent line at the inflection point) is defined as the tangent line to the rising edge on the short-wavelength side of the phosphorescence spectrum. Note that the maximum points with peak intensities of 15% or less of the maximum peak intensity of the spectrum are not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point closest to the maximum value on the shortest wavelength side where the value of the slope reaches the maximum value is defined as the tangent line to the rising edge on the short-wavelength side of the phosphorescence spectrum. For the measurement of phosphorescence, an F-4500 type spectrofluorometer main body manufactured by Hitachi High-Technologies Corporation can be used. Note that the measurement device is not limited to this, and it may be measured by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[0210] · The lowest excited singlet energy S1 As a measurement method (sometimes referred to as the solution method) of the lowest excited singlet energy S1 using a solution, the following method can be mentioned. Prepare a 10 μmol / L toluene solution of the compound to be measured, put it in a quartz cell, and measure the absorption spectrum of this sample at room temperature (300 K) (the vertical axis is the absorption intensity, and the horizontal axis is the wavelength). Draw a tangent to the downward slope on the long-wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of this tangent and the horizontal axis into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1 [eV] = 1239.85 / λedge Examples of the absorption spectrum measuring device include, but are not limited to, the spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd.

[0211] The tangent to the downward slope on the long-wavelength side of the absorption spectrum is drawn as follows. Among the maximum values of the absorption spectrum, when moving along the spectral curve in the long-wavelength direction from the maximum value on the longest-wavelength side, consider the tangents at each point on the curve. This tangent repeatedly decreases and then increases as the curve goes down (that is, as the value on the vertical axis decreases). The tangent drawn at the point where the value of the slope takes the minimum value on the longest-wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the downward slope on the long-wavelength side of the absorption spectrum. Note that the maximum points with an absorbance value of 0.2 or less are not included in the maximum value on the longest-wavelength side described above.

[0212] · Compound represented by general formula (2) In the present embodiment, the delayed fluorescence emitting material is not particularly limited as long as it is a compound having delayed fluorescence. In one embodiment, the delayed fluorescence emitting material is a compound represented by the following general formula (2).

[0213]

Chemical formula

[0214] In the general formula (2), A is an acceptor (electron-accepting) site and is a group having a partial structure selected from the following general formulas (a-1) to (a-7). When there are a plurality of As, the plurality of As may be the same as or different from each other, and the As may combine with each other to form a saturated or unsaturated ring. B is a donor (electron-donating) site and has a partial structure selected from the following general formulas (b-1) to (b-6). When there are a plurality of Bs, the plurality of Bs may be the same as or different from each other, and the Bs may combine with each other to form a saturated or unsaturated ring. a, b, and d are each independently 1, 2, 3, 4, or 5. c is 0, 1, 2, 3, 4, or 5. When c is 0, A and B are bonded by a single bond or a spiro bond. When c is 1, 2, 3, 4, or 5, L is a linking group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms. When there are a plurality of Ls, the plurality of Ls may be the same as or different from each other, and the Ls may combine with each other to form a saturated or unsaturated ring.

[0215]

Chemical formula

[0216]

Chemical formula

[0217] In the above general formulas (b-1) to (b-6), one or more sets of two or more adjacent Rs among the plurality of Rs combine with each other to form a substituted or unsubstituted monocyclic ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring. Each R is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, when a plurality of Rs are present, the plurality of Rs may be the same as or different from each other.

[0218] As an example of the bonding mode of the compound represented by the general formula (2), for example, the bonding modes shown in Table 1 below can be mentioned.

[0219] [Table 1]

[0220] · Method for producing a delayed fluorescence emitting material The delayed fluorescence emitting material can be produced by a known method. Further, the delayed fluorescence emitting material can also be produced by following a known method and using known alternative reactions and raw materials adapted to the target product.

[0221] · Specific examples of the delayed fluorescence emitting material Specific examples of the delayed fluorescence emitting material include, for example, the following compounds. However, the present invention is not limited to these specific examples of the delayed fluorescence emitting material.

[0222] [Chemical formula]

[0223] (TADF mechanism) FIG. 4 is a diagram showing an example of the relationship between the energy levels of the second compound M2 in the case of a delayed fluorescence-emitting material and the first compound M1 in the case of the compound of the first embodiment in the light-emitting layer. In FIG. 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 from S1(M2) to S1(M1) in FIG. 4 represents Förster-type energy transfer from the lowest excited singlet state of the second compound M2 to the first compound M1. As shown in FIG. 4, when a compound (delayed fluorescence-emitting material) with a small ΔST(M2) 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) by thermal energy. Then, 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 also considered that the internal quantum efficiency can be theoretically increased up to 100% by utilizing the delayed fluorescence by this TADF mechanism.

[0224] The second compound as the host material may be a compound having a higher lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material. Examples of the host material 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, (3) condensed heterocyclic compounds such as carbazole derivatives, and (4) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0225] The organic EL element of this embodiment preferably emits green light. When the organic EL element of this embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.

[0226] The measurement of the main peak wavelength of the light emitted from the organic EL element is performed as follows. The spectral radiance spectrum when a voltage is applied to the organic EL element so that the current density is 10 mA / cm 2 is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta Inc.). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is measured and taken as the main peak wavelength (unit: nm).

[0227] · 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 or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. When the thickness of the light-emitting layer is 5 nm or more, it becomes easier to form the light-emitting layer and adjust the chromaticity, and when the thickness of the light-emitting layer is 50 nm or less, an increase in the driving voltage is likely to be suppressed.

[0228] · Content ratio of the compound in the light-emitting layer The content ratios of the first compound and the second compound contained in the light-emitting layer are preferably in the following ranges, for example. The content ratio of the first compound is preferably 0.01 mass% or more and 10 mass% or less, more preferably 0.01 mass% or more and 5 mass% or less, and even more preferably 0.01 mass% or more and 2 mass% or less. The content ratio of the second compound is preferably 10 mass% or more and 80 mass% or less, more preferably 10 mass% or more and 60 mass% or less, and even more preferably 20 mass% or more and 60 mass% or less. Note that 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 thereof. The light-emitting layer may contain only one type of the second compound or two or more types thereof.

[0229] (Substrate) The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, plastic, etc. can be used. Also, a flexible substrate may be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Also, an inorganic vapor deposition film can be used.

[0230] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, and mixtures thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. can be mentioned. In addition, 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 metal materials (for example, titanium nitride) etc. can be mentioned. These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method using a target in which 1% by mass or more and 10% by mass or less of zinc oxide is added to indium oxide. Also, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method using a target containing 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide with respect to indium oxide. In addition, it may be produced by other methods such as a vacuum evaporation method, a coating method, an inkjet method, or a spin coating method. Among 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 work function of the anode. Therefore, materials possible as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, and also including elements belonging to Group 1 or Group 2 of the periodic table) can be used. Elements belonging to Group 1 or Group 2 of the periodic table, which are materials with a small work function, that is, 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 (for example, 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 an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Further, when using a silver paste or the like, a coating method or an inkjet method can be used.

[0231] (Cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having 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, i.e., 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. When forming the cathode using an alkali metal, alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. When using a silver paste or the like, a coating method or an inkjet method can be used. In addition, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium tin oxide containing silicon or silicon oxide, regardless of the work function. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, or the like.

[0232] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used. In addition, substances with high hole injection properties include aromatic amine compounds such as low-molecular-weight organic compounds 4,4’,4’’-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4’,4’’-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc. In addition, high hole injection substances can also use high molecular compounds (oligomers, dendrimers, polymers, etc.). For example, high molecular compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N’-[4-(4-diphenylamino)phenyl]phenyl-N’-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N’-bis(4-butylphenyl)-N,N’-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used. In addition, high molecular compounds added with acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0233] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. In the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and other aromatic amine compounds can be used. The substances described here are mainly substances having a hole mobility of 10-6 cm2 / Vs or more. In the hole transport layer, carbazole derivatives such as CBP, CzPA, PCzPA, and anthracene derivatives such as t-BuDNA, DNA, DPAnth may also be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, as long as it is a substance with higher hole transport properties than electrons, other substances may be used. Note that the layer containing a substance with high hole transport properties may be a single layer or a layer in which two or more layers made of the above substances are laminated.

[0234] (Electron transport layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds can be used. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. The substances described here mainly have an electron mobility of 10 -6 cm 2 / Vs or more. Note that as long as the substance has higher electron transport properties than hole transport properties, substances other than the above can also be used as the electron transport layer. Also, the electron transport layer may be a single layer or a layer in which two or more layers composed of the above substances are laminated. In addition, polymer compounds can also be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. can be used.

[0235] (Electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, or their compounds such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), etc. can be used. In addition, substances obtained by incorporating alkali metals, alkaline earth metals, or their compounds into substances having electron transporting properties, specifically, those obtained by incorporating magnesium (Mg) into Alq, etc. may also be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used for the electron injection layer. Since electrons are generated in the organic compound by the electron donor in such a composite material, it has excellent electron injection properties and electron transporting properties. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, substances (such as metal complexes and heteroaromatic compounds) constituting the above-described electron transport layer can be used. Any substance that exhibits electron donating properties with respect to the organic compound may be used as the electron donor. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. In addition, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[0236] (Layer formation method) The method for forming each layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above, and known methods such as dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, and wet film formation methods such as spin coating, dipping, flow coating, and inkjet can be employed.

[0237] (Film thickness) The film thickness of each organic layer of the organic EL element of this embodiment is not limited except as specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if it is too thick, a high applied voltage is required and the efficiency deteriorates. Therefore, a range of several nm to 1 μm is usually preferable.

[0238] Since the organic EL element according to this embodiment contains the compound of the first embodiment, its performance is improved. According to one embodiment, an organic EL element with a low driving voltage, a high EQE, and a narrow full width at half maximum of the main peak of the light emitted from the element can be provided.

[0239] 〔Fourth Embodiment〕 (Organic electroluminescence element) The configuration of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be given the same reference numerals and names, and the description will be omitted or simplified. Also, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0240] The organic EL element according to the fourth embodiment is different from the organic EL element according to the third embodiment in that the light-emitting layer further contains a third compound. Other points are the same as those in the third embodiment.

[0241] In the fourth embodiment, it is preferable that the light-emitting layer is in a form including a first compound, a second compound, and a third compound. In the case of this form, it is more preferable that the first compound is the compound of the first embodiment, and it is further preferable that the second compound is a delayed fluorescence light-emitting material. Also, in the case of this form, it is preferable that the first compound is a dopant material, and it is preferable that the second compound is a host material. Further, it is preferable that the third compound is 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 in an amount of 50% by mass or more of the total mass of the light-emitting layer, 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.

[0242] (The third compound) The third compound may be a compound having delayed fluorescence or a compound not showing delayed fluorescence.

[0243] The third compound is not particularly limited, but is preferably a compound other than an amine compound. That is, it is preferable that the third compound does not contain a substituted or unsubstituted amino group. Further, for example, as the third compound, a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative can be used, but it is not limited to these derivatives.

[0244] It is also preferable that the third compound is a compound containing at least any one of a partial structure represented by the following general formula (31), a partial structure represented by the following general formula (32), a partial structure represented by the following general formula (33A), and a partial structure represented by the following general formula (34A) in one molecule.

[0245]

Chemical formula

[0246]

Chemical formula

[0247] In the general formula (31), Y 31 ~Y 36 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, provided that at least one of Y 31 ~Y 36 is a carbon atom bonded to another atom in the molecule of the third compound, In the general formula (32), Y 41 ~Y 48 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, provided that at least one of Y 41 ~Y 48 is a carbon atom bonded to another atom in the molecule of the third compound, X 30 is a nitrogen atom, an oxygen atom, or a sulfur atom bonded to another atom in the molecule of the third compound. In the general formulas (33A) and (34A), * each independently represents a bonding site with another atom or another structure in the molecule of the third compound.

[0248] The third compound preferably has a total of 2 or more and 10 or less partial structures represented by the general formula (31) and partial structures represented by the general formula (32) in one molecule, and more preferably has 4 or more and 8 or less.

[0249] In the general formula (32), it is also preferable that at least two of Y 41 ~Y 48 are carbon atoms bonded to other atoms in the molecule of the third compound, and a ring structure containing the carbon atoms is constructed. For example, it is preferable that the partial structure represented by the general formula (32) is any partial structure selected from the group consisting of partial structures represented by the following general formulae (321), (322), (323), (324), (325), and (326).

[0250]

Chemical formula

[0251]

Chemical formula

[0252]

Chemical formula

[0253] In the general formulae (321) to (326), X 30 is, independently of each other, a nitrogen atom, an oxygen atom, or a sulfur atom that binds to another atom in the molecule of the third compound, Y 41 ~Y 48 is, independently of each other, a nitrogen atom or a carbon atom that binds to another atom in the molecule of the third compound, X 31 is, independently of each other, a nitrogen atom, an oxygen atom, a sulfur atom that binds to another atom in the molecule of the third compound, or a carbon atom that binds to another atom in the molecule of the third compound, Y 61 ~Y 64 is, independently of each other, a nitrogen atom or a carbon atom that binds to another atom in the molecule of the third compound. In the present embodiment, it is preferable that the third compound has a partial structure represented by the general formula (323) among the general formulae (321) to (326).

[0254] The partial structure represented by the general formula (31) is preferably included in the third compound as at least any one group selected from the group consisting of the group represented by the following general formula (33) and the group represented by the following general formula (34). The third compound preferably has at least any one partial structure among the partial structures represented by the following general formula (33) and the following general formula (34). Since the bonding positions are meta to each other like the partial structures represented by the following general formula (33) and the following general formula (34), the energy gap T 77K (M3) at 77 [K] of the third compound can be kept high.

[0255]

Chemical formula

[0256] In the general formula (33), Y 31 , Y 32 , Y 34 , and Y 36 are each independently a nitrogen atom or CR 31 . In the general formula (34), Y 32 , Y 34 , and Y 36 are each independently a nitrogen atom or CR 31 . In the general formulas (33) and (34), R 31 are each independently a hydrogen atom or a substituent, R 31 as a substituent are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted silyl group, A substituted germanium group, A substituted phosphine oxide group, A halogen atom, A cyano group, A nitro group, and A substituted or unsubstituted carboxy group is selected from the group consisting of. However, the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms in the said R 31 is preferably a non-condensed ring. In the general formula (33) and the general formula (34), * each independently represents a bonding site with another atom or another structure in the molecule of the third compound.

[0257] In the general formula (33), Y 31 , Y 32 , Y 34 , and Y 36 are each independently preferably CR 31 , and a plurality of R 31 are the same as or different from each other. Also, in the general formula (34), Y 32 , Y 34 , and Y 36 are each independently preferably CR 31 , and a plurality of R 31 are the same as or different from each other.

[0258] The substituted germanium group is preferably represented by -Ge(R 301 )3. R 301 are each independently a substituent. The substituent R 301 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. A plurality of R 301 are the same as or different from each other.

[0259] The partial structure represented by the general formula (32) is preferably included in the third compound as at least any one group selected from the group consisting of the following general formulas (35) to (39) and the group represented by the following general formula (30a).

[0260]

Chemical formula

[0261]

Chemical formula

[0262]

Chemical formula

[0263] In the general formula (35), Y 41 to Y 48 are each independently a nitrogen atom or CR 32 . In the general formulas (36) and (37), Y 41 to Y 45 , Y 47 , and Y 48 are each independently a nitrogen atom or CR 32 . In the general formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 , and Y 48 are each independently a nitrogen atom or CR 32 . In the general formula (39), Y 42 to Y 48 are each independently a nitrogen atom or CR 32 . In the general formula (30a), Y 42 to Y 47 are each independently a nitrogen atom or CR 32 . In the general formulas (35) to (39) and (30a), R 32 is, independently of one another, a hydrogen atom or a substituent, R as a substituent 32 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted germanium group, a substituted phosphine oxide group, a halogen atom, a cyano group, a nitro group, and a substituted or unsubstituted carboxy group selected from the group consisting of, a plurality of R 32 are the same as or different from one another. In the general formulas (37) to (39) and (30a), X 30 is NR 33 an oxygen atom, or a sulfur atom, R 33 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted germanium group, a substituted phosphine oxide group, a fluorine atom, a cyano group, a nitro group, and a substituted or unsubstituted carboxy group selected from the group consisting of, a plurality of Rs 33 are the same as or different from each other. However, the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms in the R 33 is preferably a non-condensed ring. In the general formulas (35) to (39) and (30a), * each independently represents a bonding site with another atom or another structure in the molecule of the third compound.

[0264] In the general formula (35), Y 41 ~Y 48 are each independently preferably CR 32 , in the general formulas (36) and (37), Y 41 ~Y 45 , Y 47 , and Y 48 are each independently preferably CR 32 , in the general formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 , and Y 48 are each independently preferably CR 32 , in the general formula (39), Y 42 ~Y 48 are each independently preferably CR 32 , in the general formula (30a), Y 42 ~Y 47 are each independently preferably CR 32 , and a plurality of Rs 32 are the same as or different from each other.

[0265] In the third compound, X 30is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.

[0266] In the third compound, R 31 , and R 32 are each independently a hydrogen atom or a substituent, and R 31 as a substituent, and R 32 as a substituent are each independently preferably any group selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. R 31 , and R 32 are more preferably a hydrogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. However, when R 31 as a substituent and R 32 as a substituent are a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, the aryl group is preferably a non-condensed ring.

[0267] The third compound is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

[0268] Examples of the substituents in the third compound are as follows, for example, but the present invention is not limited to these examples.

[0269] Specific examples of the aryl group (which may be referred to as an aromatic hydrocarbon group) include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a benzo[c]phenanthryl group, a benzo[g]chrysenyl group, a benzanthryl group, a triphenylenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a fluoranthenyl group, etc., and preferably include a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, a triphenylenyl group, and a fluorenyl group, etc. Examples of the aryl group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group, etc. As shown by the specific examples, the aryl group includes both a condensed aryl group and a non-condensed aryl group. As the aryl group, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, a triphenylenyl group, or a fluorenyl group is preferable.

[0270] Specific examples of the heteroaryl group (which may also be referred to as a heterocyclic group, heteroaromatic ring group, or aromatic heterocyclic group) include a pyrrolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyridyl group, triazinyl group, indolyl group, isoindolyl group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazo[1,2-a]pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, benzothienyl group, dibenzothienyl group, azadibenzothienyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, furazanyl group, benzoxazolyl group, thienyl group, thiazolyl group, thiadiazolyl group, benzothiazolyl group, triazolyl group, tetrazolyl group, etc. Preferably, a dibenzofuranyl group, dibenzothienyl group, carbazolyl group, pyridyl group, pyrimidinyl group, triazinyl group, azadibenzofuranyl group, and azadibenzothienyl group, etc. can be mentioned. As the heteroaryl group, a dibenzofuranyl group, dibenzothienyl group, carbazolyl group, pyridyl group, pyrimidinyl group, triazinyl group, azadibenzofuranyl group, or azadibenzothienyl group is preferable, and a dibenzofuranyl group, dibenzothienyl group, azadibenzofuranyl group, or azadibenzothienyl group is more preferable.

[0271] In the third compound, it is also preferable that the substituted silyl group is selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group. Specific examples of the substituted or unsubstituted trialkylsilyl group can include a trimethylsilyl group and a triethylsilyl group. Specific examples of the substituted or unsubstituted arylalkylsilyl group include a diphenylmethylsilyl group, a ditolylmethylsilyl group, a phenyldimethylsilyl group, and the like. Specific examples of the substituted or unsubstituted triarylsilyl group include a triphenylsilyl group, a tritolylsilyl group, and the like.

[0272] In the third compound, the substituted phosphine oxide group is preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include a diphenylphosphine oxide group, a ditolylphosphine oxide group, and the like.

[0273] In the third compound, examples of the substituted carboxy group include a benzoyloxy group and the like.

[0274] · Method for producing the third compound The third compound can be produced, for example, by the methods described in International Publication No. 2012 / 153780, International Publication No. 2013 / 038650, and the like. Further, for example, the third compound can be produced by using known alternative reactions and raw materials according to the target product.

[0275] · Specific examples of the third compound Specific examples of the third compound according to this embodiment are shown below. Note that the third compound in the present invention is not limited to these specific examples.

[0276]

Chemical formula

[0277]

Chemical formula

[0278]

Chemical formula

[0279]

Chem.

[0280] (Relationships among the first compound, the second compound, and the third compound in the light-emitting layer) In the organic EL element of the present embodiment, when the light-emitting layer contains a second compound and a third compound, the lowest excited singlet energy S1(M2) of the second compound and the lowest excited singlet energy S1(M3) of the third compound preferably satisfy the relationship of the following formula (Formula 2). S1(M3)>S1(M2) (Formula 2)

[0281] The energy gap T 77K (M3) at 77 [K] of the third compound is preferably larger than the energy gap T 77K (M1) at 77 [K] of the first compound. The energy gap T 77K (M3) at 77 [K] of the third compound is preferably larger than the energy gap T 77K (M2) at 77 [K] of the second compound.

[0282] 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 preferably satisfy the relationship of the following formula (Formula 2A). S1(M3)>S1(M2)>S1(M1) …(Formula 2A)

[0283] The energy gap T 77K (M1) at 77 [K] of the first compound, the energy gap T 77K (M2) at 77 [K] of the second compound, and the energy gap T 77K (M3) at 77 [K] of the third compound preferably satisfy the relationship of the following formula (Formula 2B). T77K (M3)>T 77K (M2)>T 77K (M1) …(Number 2B)

[0284] When the organic EL element of this embodiment emits light, it is preferable that in the light-emitting layer, the compound of the first embodiment mainly emits light. The organic EL element of this embodiment preferably emits green light, similar to the organic EL element of the third embodiment. When the organic EL element of this embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less. The main peak wavelength of the light emitted from the organic EL element can be measured by the same method as the organic EL element of the third embodiment.

[0285] · Content ratio of the compound in the light-emitting layer When the light-emitting layer contains a first compound, a second compound, and a third compound, the content ratios of the first compound, the second compound, and the third compound in the light-emitting layer are preferably, for example, in the following ranges. The content ratio 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 2% by mass or less. The content ratio 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 ratio of the third compound is preferably 10% by mass or more and 80% by mass or less. The upper limit of the total content ratio of the first compound, the second compound, and the third compound in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the case where materials other than the first compound, the second compound, and the third compound are included in the light-emitting layer. The light-emitting layer may contain only one type of the first compound or may contain two or more types. The light-emitting layer may contain only one type of the second compound or may contain two or more types. The light-emitting layer may contain only one type of the third compound or may contain two or more types.

[0286] FIG. 5 is a diagram showing an example of the relationship between the energy levels of the first compound, the second compound, and the third compound in the light-emitting layer. In FIG. 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound, and T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound, and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. The dashed arrow from S1(M2) to S1(M1) in FIG. 5 represents Förster-type energy transfer from the lowest excited singlet state of the second compound to the first compound. As shown in FIG. 5, when a compound with a small ΔST(M2) (delayed fluorescence-emitting material) is used as the second compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) by thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound to the first compound, 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 can be observed. It is considered that the internal quantum efficiency can be theoretically increased to 100% by utilizing the delayed fluorescence based on this TADF mechanism.

[0287] Since the organic EL element according to this embodiment contains the compound of the first embodiment, its performance is improved. According to one embodiment, an organic EL element with a low driving voltage, a high EQE, and a narrow full width at half maximum of the main peak of the light emitted from the element can be provided.

[0288] 〔Fifth Embodiment〕 (Electronic Device) The electronic device according to this embodiment is equipped with any one of the organic EL elements of the above-described embodiments. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include a display component (e.g., an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lamps.

[0289] 〔Modifications of the Embodiment〕 Note that the present invention is not limited to the above-described embodiments, and modifications, improvements, etc. within the scope that can achieve the object of the present invention are included in the present invention.

[0290] For example, the light-emitting layer is not limited to one layer, and a plurality of light-emitting layers may be stacked. When the organic EL element has a plurality of light-emitting layers, at least one organic layer may satisfy 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 plurality of light-emitting layers contains the compound of the first embodiment, for example, the other light-emitting layers may be a fluorescence-emitting type light-emitting layer or a phosphorescence-emitting type light-emitting layer that utilizes light emission by electron transition from the triplet excited state directly to the ground state. Further, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer may be used.

[0291] Also, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The barrier layer is preferably arranged in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when the barrier layer is arranged in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching a layer on the cathode side of the barrier layer (e.g., an electron transport layer). When 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. When a barrier layer is disposed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching a layer on the anode side of the barrier layer (e.g., a hole transport layer). When 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. Further, the barrier layer may be provided adjacent to the light-emitting layer so that excitation energy does not leak from the light-emitting layer to its peripheral layer. The excitons generated in the light-emitting layer are prevented from moving to a layer on the electrode side of the barrier layer (e.g., an electron transport layer and a hole transport layer, etc.). The light-emitting layer and the barrier layer are preferably joined.

[0292] In addition, the specific structure, shape, etc. in the implementation of the present invention may be other structures, etc. within the range that can achieve the object of the present invention.

Examples

[0293] Hereinafter, examples according to the present invention will be described. The present invention is not limited by these examples at all.

[0294] <Compound> The compound represented by the general formula (1) used in the production of the organic EL element of Example 1 is shown below.

[0295]

Chemical formula

[0296] The comparative compound used in the production of the organic EL element of Comparative Example 1 is shown below.

[0297]

Chemical formula

[0298] Other compounds used in the production of the organic EL elements according to the examples and comparative examples are shown below.

[0299]

Chemical formula

[0300]

Chem.

[0301]

Chem.

[0302] <Fabrication of Organic EL Device> The organic EL device was fabricated and evaluated as follows.

[0303] (Example 1) A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) having a size of 25 mm × 75 mm × 1.1 mm thick was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 1 minute. The film thickness of ITO was 130 nm. The cleaned glass substrate with the transparent electrode line was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound HT-1 and Compound HA were co-evaporated so as to cover the transparent electrode on the surface where the transparent electrode line was formed, and a hole injection layer with a film thickness of 10 nm was formed. The concentration of Compound HT-1 in the hole injection layer was 97% by mass, and the concentration of Compound HA was 3% by mass. Next, Compound HT-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 110 nm. Next, Compound HT-2 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 10 nm. Next, Compound GD-1 as the first compound, Compound TADF-1 as the second compound, and Compound D-1 as the third compound were co-evaporated on this second hole transport layer to form a light-emitting layer with a film thickness of 25 nm. The concentration of Compound TADF-1 in the light-emitting layer was 25% by mass, the concentration of Compound GD-1 was 1% by mass, and the concentration of Compound D-1 was 74% by mass. Next, Compound ET-1 was evaporated on this light-emitting layer to form a first electron transport layer with a film thickness of 5 nm. Next, compound ET-2 was vapor-deposited on this first electron transport layer to form a second electron transport layer with a film thickness of 50 nm. Next, lithium fluoride (LiF) was vapor-deposited on this second electron transport layer to form an electron-injecting electrode (cathode) with a film thickness of 1 nm. Then, metal aluminum (Al) was vapor-deposited on this electron-injecting electrode to form a metal Al cathode with a film thickness of 80 nm. The device structure of Example 1 is schematically shown as follows. ITO(130) / HT-1:HA(10, 97%:3%) / HT-1(110) / HT-2(10) / D-1:TADF-1:GD-1(25, 74%:25%:1%) / ET-1(5) / ET-2(50) / LiF(1) / Al(80) Note that the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the parentheses, the percentage numbers (97%:3%) indicate the ratio (mass%) of compound HT-1 and compound HA in the hole injection layer, and the percentage numbers (74%:25%:1%) indicate the ratio (mass%) of the third compound, the second compound, and the first compound in the light-emitting layer. The following is the same notation.

[0304] (Comparative Example 1) The organic EL device of Comparative Example 1 was fabricated in the same manner as in Example 1, except that compound GD-1 in Example 1 was replaced with the first compound described in Table 2.

[0305] <Evaluation of Organic EL Device> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 2. Also shown in Table 2 are the lowest excited singlet energy S1 and the main peak wavelength of the compound of general formula (1) used in the light-emitting layer of each example, the thermally activated delayed fluorescence properties (ΔST and Delay / Prompt ratio) of the second compound, and the lowest excited singlet energy S1, as well as the lowest excited singlet energy S1 of the third compound.

[0306] · Driving voltage (V) When the current density of the organic EL device is 10 mA / cm 2The voltage (unit: V) when an electric current was passed between the anode and the cathode was measured so as to achieve this.

[0307] ·CIE1931 chromaticity When the current density of the organic EL element was 10 mA / cm 2 The spectral emission luminance spectrum when a voltage was applied to the element so as to achieve this was measured with a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral emission luminance spectrum, CIEx and CIEy were calculated.

[0308] ·External quantum efficiency EQE When the current density of the organic EL element was 10 mA / cm 2 The spectral emission luminance spectrum when a voltage was applied to the element so as to achieve this was measured with a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta, Inc.). Assuming Lambertian emission from the obtained spectral emission luminance spectrum, the external quantum efficiency EQE (unit: %) was calculated.

[0309] ·Peak wavelength (λp) and full width at half maximum of emission FWHM When the current density of the organic EL element was 10 mA / cm 2 The spectral emission luminance spectrum when a voltage was applied to the element so as to achieve this was measured with a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral emission luminance spectrum, the peak wavelength λ p (unit: nm) was determined. Also, from the obtained spectral emission luminance spectrum, the full width at half maximum of emission FWHM (unit: nm) was measured.

[0310] [Table 2]

[0311] When comparing the organic EL device according to Example 1 with the organic EL device according to Comparative Example 1, the main peak wavelength of the device was the same, but in Example 1, the driving voltage was lower, the EQE was higher, and the full width at half maximum was narrower. By introducing a benzoindole structure like the compound represented by General Formula (1) to cause the multiple resonance effect of boron and nitrogen, it is considered that simultaneous achievement of green region emission and narrowing of the spectral full width at half maximum was achieved.

[0312] <Evaluation of Compounds> The physical property values of the compounds described in Table 2 were measured by the following methods.

[0313] (Thermally Activated Delayed Fluorescence Property) · Thermally Activated Delayed Fluorescence Property of Compound TADF-1 The thermally activated delayed fluorescence property was confirmed by measuring transient PL using the apparatus shown in Figure 2. The compound TADF-1 was dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength was prepared to remove the contribution of self-absorption. Further, to prevent quenching by oxygen, the sample solution was freeze-degassed and then sealed in a cell with a lid under an argon atmosphere to obtain a sample solution saturated with argon and free of oxygen. The fluorescence spectrum of the above sample solution was measured with a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield was calculated by Equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After excitation with pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the compound TADF-1, there are Prompt emission (instantaneous emission) immediately observed from the excited state and Delay emission (delayed emission) not immediately observed after the excitation but observed later. The delayed fluorescence emission in this example means that the amount of Delay emission (delayed emission) is 5% or more with respect to the amount of Prompt emission (instantaneous emission). Specifically, let the amount of Prompt emission (instantaneous emission) be X P and the amount of Delay emission (delayed emission) be X D When, X D / XP It means that the value of The amounts of Prompt emission and Delay emission and their ratio can be determined by a method similar to the method described in "Nature 492, 234-238, 2012" (Reference 1). Note that the apparatus used for calculating the amounts of Prompt emission and Delay emission is not limited to the apparatus described in the above Reference 1 or the apparatus described in FIG. 2. Regarding compound TADF-1, it was confirmed that the amount of Delay emission (delayed emission) is 5% or more with respect to the amount of Prompt emission (prompt emission). Specifically, for compound TADF-1, X D / X P The value of was 0.05 or more. In Table 2, "Delay / Prompt" means the value of "X D / X P ", and the value of X D / X P being ">0.05" means that the value exceeded 0.05.

[0314] ·ΔST The lowest singlet excitation energy S1 of compounds GD-1, Ref-1, TADF-1 and D-1 was measured by the above-mentioned solution method. The energy gap T 77K of compound TADF-1 at 77 [K] was measured by the energy gap T 77K measurement method described in the above-mentioned "relationship between triplet energy and energy gap at 77 [K]". Based on the measured lowest singlet excitation energy S1 and the energy gap T 77K at 77 [K], ΔST of compound TADF-1 was calculated.

[0315] · Main peak wavelength of the compound A 5 μmol / L toluene solution of the compound to be measured was prepared, placed in a quartz cell, and the fluorescence spectrum of this sample (vertical axis: fluorescence emission intensity, horizontal axis: wavelength) was measured at room temperature (300 K). In this example, the fluorescence spectrum was measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi, Ltd. Note that the fluorescence spectrum measuring device is not limited to the device used here. In the fluorescence spectrum, the peak wavelength of the fluorescence spectrum with the maximum emission intensity was defined as the main peak wavelength of the compound.

[0316] <Synthesis of Compound> (Synthesis Example 1) Synthesis of Compound GD-1 [Production of Intermediate 1-1]

[0317] [Chemical Formula]

[0318] Under an argon atmosphere, a mixture of 2-amino-3-iodonaphthalene (4.28 g), 1,2-diphenylacetylene (3.40 g), palladium(II) acetate (178 mg), tricyclohexylphosphine (446 mg), potassium carbonate (5.49 g) and N-methylpyrrolidone (360 mL) was stirred at 110 °C for 5 hours. The resulting mixture was cooled to room temperature, and after distilling off a part of N-methylpyrrolidone under reduced pressure, it was diluted with t-butyl methyl ether and added to water. The aqueous layer was extracted with t-butyl methyl ether, the organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2.78 g (55%) of Intermediate 1-1. In the reaction scheme, Pd(OAc)2 is palladium(II) acetate, Cy3P is tricyclohexylphosphine, and NMP is N-methylpyrrolidone.

[0319] [Production of Intermediate 1-2]

[0320] [Chemical Formula]

[0321] Under an argon atmosphere, a mixture of 2-bromo-1,3-difluoro-5-iodobenzene (47.8 g), phenylboronic acid (18.29 g), tripotassium phosphate (39.8 g), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.09 g), 1,4-dioxane (250 mL), and water (125 mL) was stirred at room temperature for 4 hours. Toluene (250 mL) and water (200 mL) were added to the resulting mixture, the aqueous layer was extracted with toluene, the organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 35.1 g (87%) of Intermediate 1-2. In the reaction scheme, Pd(dppf)Cl2 is [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[0322] [Production of Intermediate 1-3]

[0323] [Chemical formula]

[0324] Under an argon atmosphere, a mixture of Intermediate 1-1 (6.39 g), Intermediate 1-2 (10.76 g), tripotassium phosphate (21.23 g), and dimethylformamide (140 mL) was stirred at 105 °C for 48 hours. After distilling off some dimethylformamide under reduced pressure, it was poured into water and extracted with t-butyl methyl ether. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.2 g (55%) of Intermediate 1-3. In the reaction scheme, DMF is dimethylformamide.

[0325] [Production of Intermediate 1-4]

[0326] [Chemical formula]

[0327] Under an argon atmosphere, a mixture of intermediate 1-3 (6.14 g), 3,6-di-tert-butyl-9H-carbazole (3.32 g), tripotassium phosphate (6.88 g), and dimethylformamide (96 mL) was stirred at 105 °C for 20 hours. A portion of the dimethylformamide was distilled off under reduced pressure, and the resulting mixture was added to 150 mL of water and stirred. The precipitated solid was collected by filtration, washed with water, and then dried under reduced pressure. Further, the obtained solid was suspended in 220 mL of ethanol, heated to reflux for 1 hour, and then the solid was collected by filtration to obtain 7.31 g (82%) of intermediate 1-4.

[0328] [Production of Compound GD-1]

[0329] [Chemical Formula]

[0330] Under an argon atmosphere, intermediate 1-4 (2.23 g) was added to tert-butylbenzene (33 mL), cooled to -20 °C, and then a 1.9 M solution of tert-butyllithium in pentane (2.8 mL) was added dropwise. After the addition, the temperature was raised to 70 °C and stirred for 30 minutes, and then the components with a lower boiling point than tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -55 °C, boron tribromide (0.57 mL) was added, the temperature was raised to room temperature, and stirred for 1 hour. Then, it was cooled to 0 °C, N,N-diisopropylethylamine (1.19 mL) was added, stirred at room temperature until the exothermic reaction subsided, then the temperature was raised to 130 °C and stirred overnight. After distilling off tert-butylbenzene under reduced pressure, the residue was purified by flash chromatography to obtain 350 mg of an orange compound. As a result of mass spectrum analysis, this orange compound was the target product, and for a molecular weight of 756.8, it was 757.4 [M+H] + It was. In the reaction scheme, t-BuLi is tert-butyllithium, and DIPEA is N,N-diisopropylethylamine. [Explanation of Symbols]

[0331] 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.

Claims

1. A compound represented by the following general formula (4). 【Chemical Formula 1】 (In the general formula (4), R2, R6, R13, RQ, and Rx2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring-forming atoms, and the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring-forming atoms.)

2. R １３ and R Ｑ are each independently A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group, The compound according to claim 1.

3. All the groups described as "substituted or unsubstituted" are "unsubstituted" groups, The compound according to claim 1 or claim 2.

4. A material for an organic electroluminescence element, comprising the compound according to any one of claims 1 to 3.

5. An organic electroluminescence element having a cathode, an anode, and an organic layer contained between the cathode and the anode, wherein the organic layer includes a light-emitting layer, and at least one layer of the organic layer contains the compound according to any one of claims 1 to 3, An organic electroluminescence element.

6. The organic electroluminescence element according to claim 5, wherein the light-emitting layer contains the compound.

7. The organic electroluminescence element according to claim 5 or claim 6, wherein the light-emitting layer further contains a delayed fluorescence light-emitting material.

8. The organic electroluminescence element according to claim 7.

9. The lowest excited singlet energy S of the delayed fluorescence emitting material １ (H) and the lowest excited singlet energy S of the compound １ (D) satisfy the following mathematical formula (Formula 1): An electronic device equipped with the organic electroluminescence element according to any one of claims 5 to 8. S １ (H) > S １ (D)…(Number 1) ​ ​

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