Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device

Abstract

To provide a compound capable of improving at least one of emission efficiency and lifetime of an organic EL device.SOLUTION: As a representative compound, a compound having two 12H-[1]benzothieno[2,3-a]carbazole structures via a dicyanobenzene ring is illustrated.SELECTED DRAWING: None

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 are being conducted to improve the performance of organic EL devices.

[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 that 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 properties (hereinafter also referred to as a TADF compound), for example, a compound in which a donor site and an acceptor site are bonded within a molecule is known.

[0004] As documents related to organic EL elements and compounds used in organic EL elements, Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, Patent Document 5, and Patent Document 6 can be cited.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Patent Document 6

Summary of the Invention

Problems to be Solved by the Invention

[0006] In order to improve the performance of electronic devices such as displays, further improvement in the performance of organic EL elements is desired. The performance of organic EL elements includes luminous efficiency and lifespan.

[0007] An object of the present invention is to provide a compound capable of improving at least one of the luminous efficiency and lifespan of an organic EL element, to provide a material for an organic electroluminescence element or an organic electroluminescence element containing the compound, and to provide an electronic device equipped with the organic electroluminescence element.

Means for Solving the Problems

[0008] According to one aspect of the present invention, a compound represented by the following general formula (1) is provided.

[0009]

Chemical formula

[0010] (In the general formula (1), D 1 and D 2 are each independently a group represented by the following general formula (11), general formula (12) or general formula (13), provided that at least one of D 1 and D 2 is a group represented by the following general formula (12) or general formula (13), Rx is a halogen 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 5 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, a group represented by the following formula (12), or a group represented by the following formula (13), provided that Rx is not a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, and a substituted or unsubstituted triazinyl group.)

[0011]

Chem.

[0012]

Chem.

[0013]

Chem.

[0014] (In the general formulas (11) to (13), R 1 ~R 8 Among them, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 11 ~R 18 Among them, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 111 ~R 118 Among them, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 1 ~R 8 、R 11 ~R 18 and R 111 ~R 118 are each independently a hydrogen atom, A halogen 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, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, In the general formula (12) and the general formula (13), A, B and C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (14), (15), (15A) and (15B), This ring structure A, ring structure B and ring structure C are condensed with an adjacent ring structure at an arbitrary position, p, px and py are each independently 1, 2, 3 or 4, When p is 2, 3 or 4, the plurality of ring structures A are the same as or different from each other, When px is 2, 3 or 4, the plurality of ring structures B are the same as or different from each other, When py is 2, 3 or 4, the plurality of ring structures C are the same as or different from each other, However, D 1 and D 2 At least one of them is p is 2, 3, or 4, and the group represented by the general formula (12) contains a ring structure represented by the following general formula (15A) or (15B) as the ring structure A, or at least one of px and py is 2, 3, or 4, and the group represented by the general formula (13) contains a ring structure represented by the following general formula (15A) or (15B) as the ring structure B or the ring structure C, * in the general formulas (11) to (13) indicates the bonding position with the benzene ring in the general formula (1).)

[0015]

Chemical formula

[0016] (In the general formulas (14) and (15), R 19 and R 20 form a pair that 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 120 , and R 19 and R 20 that do not form the monocyclic ring and do not form the condensed ring are each independently the same as R 1 to R 8 in the general formula (11).)

[0017] According to one aspect of the present invention, a compound represented by the following general formula (1A) is provided.

[0018]

Chemical formula

[0019] (In the general formula (1A), D 3 and D 4 are each independently a group represented by the following general formula (11), general formula (12), or general formula (13), However, D 3 and D 4 at least one of them is a group represented by the following general formula (12) or general formula (13), Ry is a halogen atom, a substituted or unsubstituted aryl group having 13 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group having 5 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, a group represented by the following formula (12), or a group represented by the following formula (13).)

[0020]

Chemical formula

[0021]

Chemical formula

[0022]

Chemical formula

[0023] (In the general formulas (11) to (13), R 1 ~R 8 among them, one or more sets of two or more adjacent ones form Combine with each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted fused ring, or Do not combine with each other, R 11 ~R 18 Among them, one or more sets of two or more adjacent ones Combine with each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted fused ring, or Do not combine with each other, R 111 ~R 118 Among them, one or more sets of two or more adjacent ones Combine with each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted fused ring, or Do not combine with each other, R that does not form the monocyclic ring and does not form the fused ring 1 ~R 8 R 11 ~R 18 And R 111 ~R 118 Are each independently A hydrogen atom, A halogen 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, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, provided that R 1 ~R 8 、R 11 ~R 18 and R 111 ~R 118 are not unsubstituted biphenyl groups and are not substituted or unsubstituted dibenzofuranyl groups. In the general formula (12) and the general formula (13), A, B, and C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (14), (15), (15A), and (15B), and the ring structure A, the ring structure B, and the ring structure C are condensed with an adjacent ring structure at an arbitrary position, p, px, and py are each independently 1, 2, 3, or 4, when p is 2, 3, or 4, the plurality of ring structures A are the same as or different from each other, when px is 2, 3, or 4, the plurality of ring structures B are the same as or different from each other, when py is 2, 3, or 4, the plurality of ring structures C are the same as or different from each other. * in the general formulas (11) to (13) indicates the bonding position to the benzene ring in the general formula (1A).)

[0024]

Chemical formula

[0025] (In the general formulas (14) and (15), the pair of R 19 and R 20 is bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 120 and R which do not form the monocyclic ring and do not form the condensed ring 19 and R 20 are each independently the same as R in the general formula (11).) 1 ~R 8 and)

[0026] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device containing the compound according to one aspect of the present invention described above.

[0027] According to one aspect of the present invention, there is provided an organic electroluminescence device having an anode, a cathode, and an organic layer, wherein the organic layer contains the compound according to one aspect of the present invention described above as a first compound.

[0028] 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 described above.

Effect of the Invention

[0029] According to one aspect of the present invention, it is possible to provide a compound capable of improving at least one of the luminous efficiency and lifetime of an organic EL device, to provide a material for an organic electroluminescence device or an organic electroluminescence device containing the compound, and to provide an electronic device equipped with the organic electroluminescence device.

Brief Description of the Drawings

[0030]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Embodiments for Carrying Out the Invention

[0031] [Definitions] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, protium, deuterium, and tritium.

[0032] In this specification, in a chemical structural formula, at a bondable position where a symbol such as "R" or "D" representing a deuterium atom is not explicitly shown, it is assumed that a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded.

[0033] 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 shape (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 "number of ring-forming carbon atoms" described below shall be the same 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 the 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 the naphthalene ring substituted with an alkyl group is 10.

[0034] In the present specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic ring, a condensed ring, and a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute the ring (for example, hydrogen atoms that terminate the bonds of the atoms constituting the ring) and atoms included in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The same shall apply to the "number of ring-forming atoms" described below unless otherwise specified. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazoline ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the 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 of the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

[0035] In the present 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 the substituent when it is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0036] In this specification, in the expression "ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "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 the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

[0037] In this specification, an unsubstituted ZZ group represents the case where the "ZZ group which may be substituted or unsubstituted" is an "unsubstituted ZZ group", and a substituted ZZ group represents the case where the "ZZ group which may be substituted or unsubstituted" is a "substituted ZZ group". In this specification, "unsubstituted" in the case of "ZZ group which may be substituted or unsubstituted" 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, in this specification, "substituted" in the case of "ZZ group which may be substituted or unsubstituted" 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.

[0038] "Substituents described in this specification" Hereinafter, the substituents described in this specification will be described.

[0039] Unless otherwise specified in this specification, 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 in this specification, 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 in this specification, 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 in 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 in the "unsubstituted alkynyl 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 ring-forming carbon atoms in the "unsubstituted cycloalkyl group" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6. Unless otherwise specified herein, the number of ring-forming carbon atoms in the "unsubstituted arylene 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 in 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 herein, the number of carbon atoms in the "unsubstituted alkylene group" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0040] · "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 an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group"). In this specification, when simply referring to an "aryl group", it includes both "unsubstituted aryl group" and "substituted aryl group". "Aryl group of substitution" means a group in which one or more hydrogen atoms of "unsubstituted aryl group" are replaced with substituents. Examples of the "aryl group of substitution" 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 with substituents, and examples of the aryl group of substitution in the following specific example group G1B. Note that the examples of the "unsubstituted aryl group" and the examples of the "aryl group of substitution" listed here are only examples, and the "aryl group of substitution" described in this specification includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "aryl group of substitution" in the following specific example group G1B is further replaced with a substituent, and a group in which a hydrogen atom of the substituent in the "aryl group of substitution" in the following specific example group G1B is further replaced with a substituent.

[0041] · Unsubstituted aryl group (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, benzanthryl 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, benzofluoranhenyl group, perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0042]

Chemical formula

[0043]

Chemical formula

[0044] · Substituted aryl group (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.

[0045] · "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 a "heterocyclic group", it includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group". "Substituted heterocyclic group" means a group in which one or more hydrogen atoms of an "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 group in the following specific example group G2B, etc. 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 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.

[0046] 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).

[0047] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1), substituted heterocyclic groups containing an oxygen atom (specific example group G2B2), substituted heterocyclic groups containing a sulfur atom (specific example group G2B3), and groups in which one or more hydrogen atoms of the monovalent heterocyclic groups derived from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4).

[0048] · Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl 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, Phenoxazinyl group, Phenothiazinyl group, Azacarbazolyl group, and diazacarbazolyl group.

[0049] ·Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): Furyl group, Oxazolyl group, Isooxazolyl group, Oxadiazolyl group, Xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzisoxazolyl group, Phenoxazinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.

[0050] · 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), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0051] · a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0052]

Chemical formula

[0053]

Chemical formula

[0054] In the above general formulas (TEMP-16) to (TEMP-33), X Aand Y A is each independently an oxygen atom, a sulfur atom, NH, or CH 2 However, X A and Y A at least one of which is an oxygen atom, a sulfur atom, or NH. In the general formulas (TEMP-16) to (TEMP-33), X A and Y A if at least one of them is NH or CH 2 then 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 CH 2 .

[0055] · 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.

[0056] · Substituted heterocyclic group containing an oxygen atom (specific example group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-Butyldibenzofuranyl group, and the monovalent residue of spiro[9H-xanthene-9,9’-[9H]fluorene].

[0057] · Substituted heterocyclic group containing a sulfur atom (specific example group G2B3): Phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9’-[9H]fluorene].

[0058] · A group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced with substituents (Specific Example Group G2B4):

[0059] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" means one or more hydrogen atoms selected from the hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0060] · "Substituted or unsubstituted alkyl group" Specific examples of the "substituted or unsubstituted alkyl group" described in the present specification (Specific Example Group G3) 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. "The "alkyl group for substitution" means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced by substituents. Specific examples of the "alkyl group for substitution" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced by substituents, and examples of the alkyl group for substitution (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" means a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". It should be noted that the examples of the "unsubstituted alkyl group" and the examples of the "alkyl group for substitution" listed here are only examples, and the "alkyl group for substitution" described in this specification includes a group in which a hydrogen atom of the alkyl group itself in the "alkyl group for substitution" of specific example group G3B is further replaced by a substituent, and a group in which a hydrogen atom of the substituent in the "alkyl group for substitution" of specific example group G3B is further replaced by a substituent."

[0061] · 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.

[0062] · Substituted alkyl group (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.

[0063] · "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), substituted alkenyl groups (specific example group G4B), and the like. (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). It should be noted 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.

[0064] · Unsubstituted alkenyl group (specific example group G4A): vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0065] · Substituted alkenyl group (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.

[0066] · "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 referring to an "alkynyl group", it includes both an "unsubstituted alkynyl group" and a "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.

[0067] · Unsubstituted alkynyl group (specific example group G5A): ethynyl group.

[0068] · "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) and substituted cycloalkyl groups (specific example group G6B), etc. (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 a "cycloalkyl group", it includes both an "unsubstituted cycloalkyl group" and a "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 group" (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.

[0069] · Unsubstituted cycloalkyl group (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.

[0070] · Substituted cycloalkyl group (specific example group G6B): 4 - methylcyclohexyl group.

[0071] · The group represented by "-Si(R 901 )(R 902 )(R 903 )" Specific 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) 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. The plurality of G1 in -Si(G1)(G1)(G1) are the same as or different from each other. The plurality of G2 in -Si(G1)(G2)(G2) are the same as or different from each other. The plurality of G1 in -Si(G1)(G1)(G2) are the same as or different from each other. The plurality of G2 in -Si(G2)(G2)(G2) are the same as or different from each other. The plurality of G3 in -Si(G3)(G3)(G3) are the same as or different from each other. The plurality of G6 in -Si(G6)(G6)(G6) are the same as or different from each other.

[0072] · "a group represented by -O-(R 904 )" Specific examples (Specific Example Group G8) of the group represented by -O-(R 904 ) described in this specification include -O(G1), -O(G2), -O(G3), and -O(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.

[0073] · "a group represented by -S-(R 905 )" Specific examples (specific example group G9) of the group represented by -S-(R 905 ) described in this specification include -S(G1), -S(G2), -S(G3), and -S(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.[[]]

[0074] · "a group represented by -N(R 906 )(R 907 )" Specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ) described in this specification include -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(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 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

[0075] · "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, and the like.

[0076] · "Substituted or unsubstituted fluoroalkyl group" The "substituted or unsubstituted fluoroalkyl group" described in this specification 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). The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced by a substituent. In addition, the "substituted fluoroalkyl group" described in this specification 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 a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" are further replaced by a substituent. 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.

[0077] · "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, 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 a substituent. In addition, the "substituted haloalkyl 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 haloalkyl group" are further replaced by a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group" are further replaced by a substituent. 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.

[0078] · "Substituted or unsubstituted alkoxy group" Specific examples of the "substituted or unsubstituted alkoxy group" described herein include a group 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, more preferably from 1 to 18.

[0079] · "Substituted or unsubstituted alkylthio group" Specific examples of the "substituted or unsubstituted alkylthio group" described herein include a group 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, more preferably from 1 to 18.

[0080] · "Substituted or unsubstituted aryloxy group" As a specific example of the "substituted or unsubstituted aryloxy group" described in the present specification, it is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the 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.

[0081] · "Substituted or unsubstituted arylthio group" As a specific example of the "substituted or unsubstituted arylthio group" described in the present specification, it is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the 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.

[0082] · "Substituted or unsubstituted trialkylsilyl group" As a specific example of the "trialkylsilyl group" described in the present specification, it is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the 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.

[0083] · "Substituted or unsubstituted aralkyl group" Specific examples of the "substituted or unsubstituted aralkyl group" described in this specification are groups represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is a form of a "substituted alkyl group". An "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, more preferably 7 to 18, unless otherwise specified in this specification. Specific examples of the "substituted or unsubstituted aralkyl group" include a 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.

[0084] Unless otherwise specified in this specification, 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.

[0085] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic group described herein 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.

[0086] In this specification, unless otherwise specified herein, the carbazolyl group is specifically one of the following groups.

[0087]

Chemical formula

[0088] In this specification, unless otherwise specified herein, the (9-phenyl)carbazolyl group is specifically one of the following groups.

[0089]

Chemical formula

[0090] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents the bonding position.

[0091] In this specification, unless otherwise specified herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups.

[0092]

Chemical formula

[0093] In the general formulas (TEMP-34) to (TEMP-41), * represents the bonding position.

[0094] 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.

[0095] · "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.

[0096] · "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.

[0097] · "Substituted or unsubstituted alkylene group" The "substituted or unsubstituted alkylene group" described in this specification is, unless otherwise specified, 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, etc.

[0098] The substituted or unsubstituted arylene group described in this specification is, unless otherwise specified in this specification, preferably a group of any of the following general formulas (TEMP-42) to (TEMP-68).

[0099]

Chemical formula

[0100]

Chemical formula

[0101] In the above general formulas (TEMP-42) to (TEMP-52), Q 1 ~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.

[0102]

Chemical formula

[0103] In the above general formulas (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent. Formula Q 9 and Q 10They 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.

[0104]

Chemical formula

[0105] In the general formulas (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68), * represents the bonding position.

[0106] Unless otherwise described herein, the substituted or unsubstituted divalent heterocyclic group described herein is preferably a group of any of the following general formulas (TEMP-69) to (TEMP-102).

[0107]

Chemical formula

[0108]

Chemical formula

[0109]

Chemical formula

[0110] In the general formulas (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.

[0111]

Chemical formula

[0112] [Chemical formula]

[0113] [Chemical formula]

[0114] [Chemical formula]

[0115] In the general formulas (TEMP-83) to (TEMP-102) above, Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0116] The above is the description of "the substituents described in this specification".

[0117] · "When combining to form a ring" In this specification, the case of "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other" means the case of "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocyclic ring", the case of "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted condensed ring", and the case of "one or more sets of two or more adjacent groups do not combine with each other". In this specification, for the case of "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "the case of combining 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.

[0118]

Chem.

[0119] For example, in the case where “one or more sets of two or more adjacent ones among R 921 ~R 930 are combined with each other to form a ring”, the set of two adjacent ones that forms one set refers to the set of R 921 and R 922 , the set of R 922 and R 923 , the set of R 923 and R 924 , the set of R 924 and R 930 , the set of R 930 and R 925 , the set of R 925 and R 926 , the set of R 926 and R 927 , the set of R 927 and R 928 , the set of R 928 and R 929 , and the set of R 929 and R 921 .

[0120] The above “one or more sets” means that two or more sets of the above sets of two or more adjacent ones may form a ring at the same time. For example, when 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 , the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0121]

Chem.

[0122] The case where a "set consisting of two or more adjacent elements" forms a ring includes not only the case where a "set of two" adjacent elements is combined as in the above example, but also the case where a "set of three or more" adjacent elements is combined. For example, R 921 and R 922 are combined with each other to form ring Q A and R 922 and R 923 are combined with each other to form ring Q C and a set consisting of three adjacent elements (R 921 , R 922 and R 923 ) are combined with each other to form a ring and condense with the anthracene skeleton. 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 .

[0123]

Chemical formula

[0124] 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 set of two adjacent elements" 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". 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 . Ring Q A in the general formula (TMEP-104)If it is a benzene ring, ring Q A is a monocyclic ring. Ring Q in the general formula (TMEP-104) A If it is a naphthalene ring, ring Q A is a condensed ring.

[0125] The "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" means an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G1 are terminated by hydrogen atoms. Specific examples of the aromatic heterocyclic ring include structures in which the aromatic heterocyclic ring groups listed as specific examples in specific example group G2 are terminated by hydrogen atoms. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G6 are terminated by hydrogen atoms. "Forming a ring" means forming a ring with only a plurality of atoms of the mother skeleton or a plurality of atoms of the mother 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 ring Q A 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. As a specific example, when R 921 and R 922 form ring Q A , when a monocyclic 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.

[0126] Here, "any element" is, unless otherwise specified herein, preferably at least one element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element. In any element (for example, in the case of a carbon element or a nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "optional substituent" described later. When any element other than the carbon element is included, the formed ring is a heterocyclic ring. The "one or more arbitrary elements" constituting a monocyclic or condensed ring are, unless otherwise specified herein, preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still 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 ones" "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 ones are bonded to each other to form a substituted or unsubstituted "unsaturated ring" composed of a plurality of atoms of the main skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

[0127] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional 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 of the sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of the sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted condensed ring" (the case of "bonding to form a ring").

[0128] · 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 "arbitrary substituent" in this 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, a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, etc., 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, It is 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, the two or more R R 902 When two or more R 902 exist, the two or more R R 903 When two or more R 903 exist, the two or more R R 904 When two or more R 904 exist, the two or more R R 905 When two or more R 905 exist, the two or more R R 906 When two or more R 906 exist, the two or more R R 907 When two or more R 907 exist, they are the same as or different from each other.

[0129] 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 group selected from the group consisting of a heterocyclic group having 5 to 50 ring-forming atoms.

[0130] 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 group selected from the group consisting of a heterocyclic group having 5 to 18 ring-forming atoms.

[0131] 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" mentioned above.

[0132] Unless otherwise specified in this specification, 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 form a benzene ring. Unless otherwise specified in this specification, any substituent may further have a substituent. The substituents that any substituent further has are the same as the above-mentioned arbitrary substituents.

[0133] In this specification, 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.

[0134] 〔First Embodiment〕 The compound according to the first embodiment is a compound represented by the following general formula (1).

[0135]

Chemical formula

[0136] (In the above general formula (1), D 1 and D 2 are each independently a group represented by the following general formula (11), general formula (12) or general formula (13), provided that at least one of D 1 and D 2 is a group represented by the following general formula (12) or general formula (13), Rx is a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a ring, A substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, A substituted or unsubstituted alkyl group having 5 to 6 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, A substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, A substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, A group represented by the following formula (12), or A group represented by the following formula (13), provided that Rx is not a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, and a substituted or unsubstituted triazinyl group.)

[0137]

Chemical formula

[0138]

Chemical formula

[0139]

Chemical formula

[0140] (In the general formulas (11) to (13), R 1 ~R 8 Among them, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, R 11 ~R 18 Among them, one or more sets of combinations consisting of two or more adjacent ones are 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, R 111 ~R 118 Among them, one or more sets of combinations consisting of two or more adjacent ones are 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, Those that do not form the monocyclic ring and do not form the condensed ring, R 1 ~R 8 R 11 ~R 18 And R 111 ~R 118 Are each independently A hydrogen atom, A halogen 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, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, In the general formula (12) and the general formula (13), A, B, and C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (14), (15), (15A), and (15B), This ring structure A, ring structure B, and ring structure C are condensed with an adjacent ring structure at an arbitrary position, p, px, and py are each independently 1, 2, 3, or 4, When p is 2, 3, or 4, the plurality of ring structures A are the same as or different from each other, When px is 2, 3, or 4, the plurality of ring structures B are the same as or different from each other, When py is 2, 3, or 4, the plurality of ring structures C are the same as or different from each other, However, D 1 and D 2 At least one of them is A group represented by the general formula (12) in which p is 2, 3, or 4 and includes a ring structure represented by the following general formula (15A) or (15B) as the ring structure A, or A group represented by the general formula (13) in which at least one of px and py is 2, 3, or 4 and includes a ring structure represented by the following general formula (15A) or (15B) as the ring structure B or ring structure C, In the general formulas (11) to (13), * indicates the bonding position with the benzene ring in the general formula (1).)

[0141]

Chemical formula

[0142] (In the general formulas (14) and (15), The pair of R 19 and R 20 Combines with each other to form a substituted or unsubstituted monocyclic ring, or ​Combine with each other to form a substituted or unsubstituted fused ring, or Do not combine with each other, R 120 , and R that does not form the monocyclic ring and does not form the fused ring 19 and R 20 are each independently the same as R in the general formula (11) 1 ~R 8 .)

[0143] The compound according to the first embodiment (the compound represented by the general formula (1)) has D 1 and D 2 respectively bonded to the 4-position and 6-position carbon atoms of 1,3-dicyanobenzene, Rx satisfying specific requirements bonded to the 2-position carbon atom, and no substituent bonded to the 5-position carbon atom. D 1 and D 2 have a skeleton with a donor property and a high lowest excited triplet energy, and thus have a function of suppressing thermal deactivation from the lowest excited triplet state. In addition, since no substituent is bonded to the 5-position carbon atom of 1,3-dicyanobenzene in the compound according to the first embodiment, the axial rotation of the molecule is suppressed. As a result, it is considered that the functions of D 1 and D 2 (the function of suppressing thermal deactivation from the lowest excited triplet state) are more likely to be expressed. Therefore, according to the compound according to the first embodiment, for example, compared with a compound in which D 1 and D 2 are respectively bonded to the 4-position and 6-position carbon atoms of 1,3-dicyanobenzene and a substituent is bonded to the 5-position carbon atom, the luminous efficiency of the organic EL element can be improved.

[0144] In the general formula (12), it is preferable that any combination of two or more adjacent ones among R 11 ~R 18 do not bond to each other. In the general formula (12), R 11 ~R 18Among them, it is also preferable that a group consisting of two or more adjacent ones be bonded to each other to form a substituted or unsubstituted monocyclic ring, or be bonded to each other to form a substituted or unsubstituted condensed ring. In the general formula (13), R 111 ~R 118 Among them, it is preferable that any group consisting of two or more adjacent ones is not bonded to each other. In the general formula (13), R 111 ~R 118 Among them, it is also preferable that a group consisting of two or more adjacent ones be bonded to each other to form a substituted or unsubstituted monocyclic ring, or be bonded to each other to form a substituted or unsubstituted condensed ring.

[0145] The compound according to the first embodiment preferably has at least one group represented by the general formula (12). The compound according to the first embodiment preferably has two groups represented by the general formula (12).

[0146] In the general formula (12), p is preferably 2 or 3, and more preferably 2. In the general formula (13), px and py are each independently preferably 2, 3 or 4.

[0147] In the compound according to the first embodiment, D 1 and D 2 At least one of them is preferably a group represented by the general formula (12) in which p is 2 or 3 and the ring structure A includes a ring structure represented by the general formula (15A) or (15B). In the compound according to the first embodiment, D 1 and D 2 At least one of them is preferably a group represented by the general formula (12) in which p is 2 and the ring structure A includes a ring structure represented by the general formula (15A) or (15B).

[0148] In the compound according to the first embodiment, the ring structure A, the ring structure B, and the ring structure C are each independently preferably any ring structure selected from the group consisting of the ring structures represented by the general formulas (14), (15A), and (15B).

[0149] In the compound according to the first embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of the groups represented by the following general formulas (12A), (12B), (12C), (12D), (12E), and (12F).

[0150]

Chemical formula

[0151]

Chemical formula

[0152]

Chemical formula

[0153]

Chemical formula

[0154]

Chemical formula

[0155]

Chemical formula

[0156] (In the general formulas (12A), (12B), (12C), (12D), (12E), and (12F), X 1 is NR 120 , a sulfur atom, or an oxygen atom, and R 11 ~R18 is, independently of each other, R in the general formula (12) 11 ~R 18 and has the same meaning as R 19 and R 20 are, independently of each other, R in the general formula (14) 19 and R 20 and has the same meaning as R 120 is R in the general formula (15) 120 and has the same meaning as In the compounds according to the first embodiment, the * in the general formulas (12A), (12B), (12C), (12D), (12E) and (12F) indicates the bonding position to the benzene ring in the general formula (1).)

[0157] In the compounds according to the first embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of the groups represented by the general formulas (12A), (12D) and (12F). In the compounds according to the first embodiment, the group represented by the general formula (12) is preferably the group represented by the general formula (12F). In the compounds according to the first embodiment, the group represented by the general formula (12) is any group selected from the group consisting of the groups represented by the general formulas (12A), (12D) and (12F), and X 1 is preferably an oxygen atom or a sulfur atom.

[0158] In the compounds according to the first embodiment, the compound represented by the general formula (1) is preferably a compound represented by any of the following general formulas (1-1) to (1-6).

[0159]

Chemical formula

[0160]

Chemical formula

[0161] [Chemical formula]

[0162] (In the general formulas (1-1) to (1-6), Rx, X 1 and R 11 ~R 20 are each independently the same as Rx, X 1 and R 11 ~R 20 in the general formula (1).)

[0163] In the compound according to the first embodiment, X 1 is preferably an oxygen atom or a sulfur atom.

[0164] In the compound according to the first embodiment, R 1 ~R 8 , R 11 ~R 20 , R 111 ~R 118 and R 120 are each 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.

[0165] In the compound according to the first embodiment, R 1 ~R 8 , R 11 ~R 20 , R 111 ~R 118 and R 120 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 6 ring-forming carbon atoms. In the compound according to the first embodiment, R 1 ~R 8 , R11 ~R 20 and R 111 ~R 118 is each independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted cycloalkyl group having 3 to 6 ring-forming carbon atoms.

[0166] In the compound according to the first embodiment, R 120 is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms. In the compound according to the first embodiment, R 120 is more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring-forming atoms.

[0167] Rx is a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkyl group having 5 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted quinolidinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted cinnolyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted morpholino group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted diazacarbazolyl group.A substituted or unsubstituted frill group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzoisoxazolyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted morpholino group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted azadibenzofuranyl group, a substituted or unsubstituted diazadibenzofuranyl group, a substituted or unsubstituted azanaphthobenzofuranyl group, a substituted or unsubstituted diazanaphthobenzofuranyl group. A substituted or unsubstituted thienyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isobenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzoisothiazolyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted dinaphthothiophenyl group, a substituted or unsubstituted azadibenzothiophenyl group, a substituted or unsubstituted diazadibenzothiophenyl group, a substituted or unsubstituted azanaphthobenzothiophenyl group, a substituted or unsubstituted diazanaphthobenzothiophenyl group, the group represented by the formula (12), or the group represented by the formula (13) is preferred.

[0168] In the compound according to the first embodiment, Rx is preferably a halogen atom, an unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, an unsubstituted alkyl group having 5 to 6 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted arylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, an unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, an unsubstituted quinolyl group, an unsubstituted isoquinolyl group, an unsubstituted quinazolinyl group, an unsubstituted benzimidazolyl group, an unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted diazacarbazolyl group, an unsubstituted dibenzofuranyl group, an unsubstituted naphthobenzofuranyl group, an unsubstituted azadibenzofuranyl group, an unsubstituted diazadibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted naphthobenzothiophenyl group, an unsubstituted azadibenzothiophenyl group, or an unsubstituted diazadibenzothiophenyl group.

[0169] In the compound according to the first embodiment, Rx is preferably an unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, an unsubstituted alkyl group having 5 to 6 carbon atoms, an unsubstituted quinolyl group, an unsubstituted isoquinolyl group, an unsubstituted quinazolinyl group, an unsubstituted benzimidazolyl group, an unsubstituted phenanthrolinyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted diazacarbazolyl group, an unsubstituted dibenzofuranyl group, an unsubstituted naphthobenzofuranyl group, an unsubstituted azadibenzofuranyl group, an unsubstituted diazadibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted naphthobenzothiophenyl group, an unsubstituted azadibenzothiophenyl group, or an unsubstituted diazadibenzothiophenyl group. In the compound according to the first embodiment, Rx is more preferably a substituted or unsubstituted phenyl group.

[0170] In the compound according to the first embodiment, when it is "substituted or unsubstituted", the substituent is preferably "unsubstituted".

[0171] (Method for producing the compound according to the first embodiment) The compound according to the first embodiment can be produced according to the synthesis method described in the examples below, or by using known alternative reactions and raw materials modeled after the synthesis method, adjusted according to the target product.

[0172] (Specific examples of the compound according to the first embodiment) Specific examples of the compound according to the first embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples. In this specification, deuterium atoms are represented as D in the chemical formula, hydrogen atoms are represented as H or the description is omitted.

[0173]

Chemical formula

[0174]

Chemical formula

[0175]

Chemical formula

[0176]

Chemical formula

[0177]

Chemical formula

[0178]

Chemical formula

[0179] [Chemistry]

[0180] [Chemistry]

[0181] [Chemistry]

[0182] [Chemistry]

[0183] [Chemistry]

[0184] [Chemistry]

[0185] [Chemistry]

[0186] [Second Embodiment] The compound according to the second embodiment is a compound represented by the following general formula (1A).

[0187] [Chemistry]

[0188] (In the general formula (1A), D 3 and D 4 are each independently a group represented by the following general formula (11), general formula (12) or general formula (13), provided that D 3 and D 4At least one of them is a group represented by the following general formula (12) or general formula (13), Ry is, a halogen atom, a substituted or unsubstituted aryl group having 13 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group having 5 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, a group represented by the following formula (12), or a group represented by the following formula (13).)

[0189]

Chemical formula

[0190]

Chemical formula

[0191]

Chemical formula

[0192] (In the general formulas (11) to (13), R 1 ~R 8 Among them, one or more sets of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, or Combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, R 11 ~R 18 Among them, one or more sets of two or more adjacent ones form a group, 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, R 111 ~R 118 Among them, one or more sets of two or more adjacent ones form a group, 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, R that does not form the monocyclic ring and does not form the condensed ring 1 ~R 8 、R 11 ~R 18 and R 111 ~R 118 are each independently, a hydrogen atom, a halogen 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, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, provided that R 1 ~R 8 , R 11 ~R 18 and R 111 ~R 118 are not unsubstituted biphenyl groups and are not substituted or unsubstituted dibenzofuranyl groups, In the general formula (12) and the general formula (13), A, B, and C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (14), (15), (15A), and (15B), and the ring structure A, the ring structure B, and the ring structure C are condensed with an adjacent ring structure at an arbitrary position, p, px, and py are each independently 1, 2, 3, or 4, when p is 2, 3, or 4, the plurality of ring structures A are the same as or different from each other, when px is 2, 3, or 4, the plurality of ring structures B are the same as or different from each other, when py is 2, 3, or 4, the plurality of ring structures C are the same as or different from each other, * in the general formulas (11) to (13) indicates the bonding position with the benzene ring in the general formula (1A).)

[0193]

Chemical formula

[0194] (In the general formulas (14) and (15), the pair of R 19 and R 20 is bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 120, and R which does not form the monocyclic ring and does not form the condensed ring 19 and R 20 are each independently the same as R 1 ~R 8 in the general formula (11).)

[0195] In the compound according to the second embodiment (the compound represented by the general formula (1A)), D 3 and D 4 are respectively bonded to the 4-position and 6-position carbon atoms of 1,3-dicyanobenzene, Ry that satisfies specific requirements is bonded to the 5-position carbon atom, and no substituent is bonded to the 2-position carbon atom. Since no substituent is bonded to the 2-position carbon atom of 1,3-dicyanobenzene in the compound according to the second embodiment, the steric hindrance of the molecule is reduced, and the molecules are likely to approach each other. As a result, it is considered that the hopping probability of carriers is improved by increasing the overlap of the orbits between molecules, and the carrier transport property is improved. Therefore, according to the compound according to the second embodiment, for example, compared with a compound in which D 3 and D 4 are respectively bonded to the 4-position and 6-position carbon atoms of 1,3-dicyanobenzene and a substituent is bonded to the 2-position carbon atom, the lifetime of the organic EL element can be improved.

[0196] In the compound according to the second embodiment, when Ry is a substituted or unsubstituted aryl group, the number of ring-forming carbon atoms of the aryl group is 13 or more and 30 or less. In the compound according to the second embodiment, when Ry is a substituted or unsubstituted aryl group having 13 to 30 ring-forming carbon atoms, for example, compared with the case where Ry is a phenyl group, the orbit spreads more widely, so the orbits are more likely to overlap between molecules, and it is considered that the effect of improving the carrier transport property is more likely to be exhibited. Therefore, according to the compound according to the second embodiment, the lifetime of the organic EL element can be improved compared with the case where Ry is a phenyl group.

[0197] In the general formula (12), R11 ~R 18 Among them, it is preferable that any combination consisting of two or more adjacent ones does not bond to each other. In the general formula (12), R 11 ~R 18 Among them, it is also preferable that a combination consisting of two or more adjacent ones bonds to each other to form a substituted or unsubstituted monocyclic ring or bonds to each other to form a substituted or unsubstituted condensed ring. In the general formula (13), R 111 ~R 118 Among them, it is preferable that any combination consisting of two or more adjacent ones does not bond to each other. In the general formula (13), R 111 ~R 118 Among them, it is also preferable that a combination consisting of two or more adjacent ones bonds to each other to form a substituted or unsubstituted monocyclic ring or bonds to each other to form a substituted or unsubstituted condensed ring.

[0198] The compound according to the second embodiment preferably has at least one group represented by the general formula (12). The compound according to the second embodiment preferably has two groups represented by the general formula (12).

[0199] In the general formula (12), p is preferably 2 or 3, and more preferably 2. In the general formula (13), px and py are each independently preferably 2, 3, or 4.

[0200] In the compound according to the second embodiment, D 3 and D 4 Among them, at least one is preferably a group represented by the general formula (12) in which p is 2 or 3 and the ring structure A includes the ring structure represented by the general formula (15A) or (15B). In the compound according to the second embodiment, D 3 and D 4At least one of them is preferably a group represented by the general formula (12) in which p is 2 and the ring structure A includes a ring structure represented by the general formula (15A) or (15B). In the compound according to the second embodiment, the ring structure A, the ring structure B, and the ring structure C are each preferably any ring structure selected from the group consisting of the ring structures represented by the general formulas (14), (15A), and (15B).

[0201] In the compound according to the second embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of the groups represented by the general formulas (12A), (12B), (12C), (12D), (12E), and (12F). However, * in the general formulas (12A), (12B), (12C), (12D), (12E), and (12F) indicates the bonding position with the benzene ring in the general formula (1A).

[0202] In the compound according to the second embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of the groups represented by the general formulas (12A), (12D), and (12F). In the compound according to the second embodiment, the group represented by the general formula (12) is preferably the group represented by the general formula (12F). In the compound according to the second embodiment, the group represented by the general formula (12) is any group selected from the group consisting of the groups represented by the general formulas (12A), (12D), and (12F), and X 1 is preferably an oxygen atom or a sulfur atom.

[0203] In the compound according to the second embodiment, the compound represented by the general formula (1A) is preferably a compound represented by any of the following general formulas (1-1A) to (1-6A).

[0204]

Chemical formula

[0205]

Chem.

[0206]

Chem.

[0207] (In the general formulas (1-1A) to (1-6A), Ry, X 1 and R 11 ~R 20 are each independently the same as Ry, X 1 and R 11 ~R 20 in the general formula (1A).)

[0208] In the compound according to the second embodiment, X 1 is preferably an oxygen atom or a sulfur atom.

[0209] In the compound according to the second embodiment, R 1 ~R 8 、R 11 ~R 18 、R 111 ~R 118 and R 120is, independently of each other, a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl 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 alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted phenyl group (preferably an unsubstituted phenyl group), a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted benzoanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzofluoranthenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group,A substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted quinolidinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted cinnolyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted morpholino group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted diazacarbazolyl group. A substituted or unsubstituted furyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzisoxazolyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted morpholino group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted azadibenzofuranyl group, a substituted or unsubstituted diazadibenzofuranyl group, a substituted or unsubstituted azanaphthobenzofuranyl group, a substituted or unsubstituted diazanaphthobenzofuranyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isobenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzisothiazolyl group,It is preferably a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted dinaphthothiophenyl group, a substituted or unsubstituted azadibenzothiophenyl group, a substituted or unsubstituted diazadibenzothiophenyl group, a substituted or unsubstituted azanaphthobenzothiophenyl group, or a substituted or unsubstituted diazanaphthobenzothiophenyl group.,

[0210] In the compound according to the second embodiment, R 1 ~R 8 、R 11 ~R 20 、R 111 ~R 118 and R 120is, independently of each other, a hydrogen atom, a substituted or unsubstituted alkyl 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 phenyl group (preferably an unsubstituted phenyl group), a substituted or unsubstituted naphthyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted isoindolyl group, a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted quinolidinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted cinnolyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted morpholino group, a substituted or unsubstituted furyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted morpholino group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted isothiazolyl group, or a substituted or unsubstituted thiadiazolyl group, preferably.

[0211] In the compound according to the second embodiment, R 1 ~R 8 、R 11 ~R 20 and R 111 ~R 118is, independently of each other, a hydrogen atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted imidazolyl group, an unsubstituted pyrazolyl group, an unsubstituted triazolyl group, an unsubstituted tetrazolyl group, an unsubstituted oxazolyl group, an unsubstituted isoxazolyl group, an unsubstituted oxadiazolyl group, an unsubstituted thiazolyl group, an unsubstituted isothiazolyl group, an unsubstituted thiadiazolyl group, an unsubstituted pyridyl group, an unsubstituted pyridazinyl group, an unsubstituted pyrimidinyl group, an unsubstituted pyrazinyl group, an unsubstituted triazinyl group, an unsubstituted indolyl group, an unsubstituted isoindolyl group, an unsubstituted indolizinyl group, an unsubstituted quinolizinyl group, an unsubstituted quinolyl group, an unsubstituted isoquinolyl group, an unsubstituted cinnolyl group, an unsubstituted phthalazinyl group, an unsubstituted quinazolinyl group, an unsubstituted quinoxalinyl group, an unsubstituted benzimidazolyl group, an unsubstituted indazolyl group, an unsubstituted morpholino group, an unsubstituted furyl group, an unsubstituted oxazolyl group, an unsubstituted isoxazolyl group, an unsubstituted oxadiazolyl group, an unsubstituted morpholino group, an unsubstituted thienyl group, an unsubstituted thiazolyl group, an unsubstituted isothiazolyl group, or an unsubstituted thiadiazolyl group, preferably.

[0212] In the compound according to the second embodiment, R 120 is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms. In the compound according to the second embodiment, R 120 is more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring-forming atoms.

[0213] In the compound according to the second embodiment, Ry is preferably a halogen atom, a substituted or unsubstituted aryl group having 13 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 ring-forming atoms, or a substituted or unsubstituted alkyl group having 5 to 6 carbon atoms.

[0214] In the compound according to the second embodiment, Ry is preferably a halogen atom, an unsubstituted aryl group having 13 to 30 ring-forming carbon atoms, an unsubstituted heteroaryl group having 6 to 30 ring-forming atoms, or an unsubstituted alkyl group having 5 to 6 carbon atoms. In the compound according to the second embodiment, Ry is more preferably a substituted or unsubstituted phenyl group.

[0215] In the compound according to the second embodiment, the substituent in the case of "substituted or unsubstituted" is preferably "unsubstituted".

[0216] (Method for producing the compound according to the second embodiment) The compound according to the second embodiment can be produced according to the synthesis method described in the examples below, or by using known alternative reactions and raw materials adapted to the target product following the synthesis method.

[0217] (Specific examples of the compound according to the second embodiment) Specific examples of the compound according to the second embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples.

[0218] [Chemical formula]

[0219] [Chemical formula]

[0220] [Chemical formula]

[0221] [Chemical formula]

[0222] [Chemical formula]

[0223]

Chem.

[0224]

Chem.

[0225]

Chem.

[0226]

Chem.

[0227]

Chem.

[0228]

Chem.

[0229]

Chem.

[0230] Hereinafter is the description common to the first embodiment and the second embodiment. The embodiment common to the first embodiment and the second embodiment may be referred to as "the above embodiment" or "the first embodiment or the second embodiment". The compound according to the above embodiment is preferably a delayed fluorescence compound.

[0231] ·Delayed fluorescence Regarding delayed fluorescence, it is explained on pages 261 to 268 of "Device Physical Properties of Organic Semiconductors" (edited by Chihaya Adachi, 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 reduced, it is explained that 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 thermally activated delayed fluorescence (TADF) is exhibited. Furthermore, the mechanism of delayed fluorescence generation is explained in Figure 10.38 in the said literature. The compound according to the above embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0232] Generally, the emission of delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0233] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurement. Transient PL measurement is a method of irradiating a sample with a pulsed laser to excite it and measuring the decay behavior (transient characteristics) of the PL emission after the irradiation is stopped. The PL emission in a TADF material is classified into an emission component from singlet excitons generated by the first PL excitation and an emission 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 time 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.

[0234] Figure 1 shows a schematic diagram of an exemplary apparatus for measuring transient PL. A method for measuring transient PL using Figure 1 and an example of analyzing the behavior of delayed fluorescence will be described.

[0235] The transient PL measurement device 100 in FIG. 1 includes a pulse 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 forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device described in FIG. 1.

[0236] The sample accommodated in the sample chamber 102 is obtained by forming a thin film in which a doping material is doped at a concentration of 12% by mass with respect to a matrix material on a quartz substrate.

[0237] A pulse laser is irradiated from the pulse laser unit 101 to the thin film sample accommodated in the sample chamber 102 to excite the doping material. Light emission is extracted in a direction 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is spectroscopically analyzed 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 in which the vertical axis is the emission intensity and the horizontal axis is the wavelength can be obtained. Also, when the two-dimensional image is cut out along the wavelength axis, a decay curve (transient PL) in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is time can be obtained.

[0238] For example, using the following reference compound H1 as the matrix material and the following reference compound D1 as the doping material, a thin film sample A was produced as described above, and transient PL measurement was performed.

[0239]

Chemical formula

[0240] 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.

[0241] Figure 2 shows the decay curves obtained from the transient PL measured for the thin-film sample A and the thin-film sample B.

[0242]

Chemical formula

[0243] As described above, by transient PL measurement, a luminescence decay curve can be obtained with the vertical axis representing the luminescence intensity and the horizontal axis representing time. 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.

[0244] Specifically, as the luminescence from a material with delayed fluorescence properties, there are Prompt emission (instantaneous emission) and Delay emission (delayed emission). Prompt emission (instantaneous emission) is the emission immediately observed from the excited state after excitation with pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the material with delayed fluorescence properties. Delay emission (delayed emission) is the emission that is not immediately observed after excitation with the pulsed light but is observed later.

[0245] The amounts and ratio of Prompt emission and Delay emission 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 Reference 1 or the apparatus described in Figure 1.

[0246] In addition, for the measurement of the delayed fluorescence property of the compound according to the above embodiment, a sample prepared by the following method is used. For example, the compound according to the above embodiment is dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength is prepared to remove the contribution of self-absorption. Further, in order to prevent quenching by oxygen, after the sample solution is freeze-degassed, it is sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above sample solution is measured with a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield is calculated by equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0247] In the above embodiment, the amount of Prompt emission (instantaneous emission) of the compound to be measured is X P and the amount of Delay emission (delayed emission) is X D When this is the case, it is preferable that the value of X D / X P is 0.05 or more. The measurement of the amount and ratio of Prompt emission and Delay emission of compounds other than the compound according to the above embodiment in this specification is also the same as the measurement of the amount and ratio of Prompt emission and Delay emission of the compound according to the above embodiment.

[0248] ·ΔST In the above embodiment, the difference (S 1 -T 77K ) between the lowest excited singlet energy S 1 and the energy gap T 77K at 77 [K] is defined as ΔST.

[0249] The lowest excited singlet energy S 1 (M1) of the compound according to the above embodiment and the energy gap T 77K(M1), the difference ΔST(M1) is preferably less than 0.3 eV, more preferably less than 0.2 eV, and even more preferably less than 0.1 eV. That is, ΔST(M1) preferably satisfies the relationship of the following mathematical formulas (Formula 10), (Formula 11), (Formula 12), or (Formula 13). ΔST(M1)=S 1 (M1)-T 77K (M1)<0.3eV …(Formula 10) ΔST(M1)=S 1 (M1)-T 77K (M1)<0.2eV …(Formula 11) ΔST(M1)=S 1 (M1)-T 77K (M1)<0.1eV …(Formula 12) ΔST(M1)=S 1 (M1)-T 77K (M1)<0.01eV…(Formula 13)

[0250] ·Relationship between triplet energy and energy gap at 77 [K] Here, the relationship between the triplet energy and the energy gap at 77 [K] will be described. In the above 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 of 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 the above embodiments, the thermally activated delayed fluorescence compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at a low temperature (77 [K]), and the singlet excited state and the triplet excited state coexist. As a result, the spectrum measured in the same manner as above includes luminescence from both the singlet excited state and the triplet excited state, and it is difficult to distinguish from which state the luminescence occurs, but basically the value of the triplet energy is considered to be dominant. Therefore, in the above embodiment, although the normal triplet energy T and the measurement method are the same, in order to distinguish that they are different in a strict sense, the value measured as follows is defined as the energy gap T 77K . 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] is used to calculate the energy amount from the following conversion formula (F1) as the energy gap T 77K at 77 [K]. Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[0251] 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 to the maximum value on the shortest-wavelength side among the maximum values of the spectrum, tangents at each point on the curve are considered in the long-wavelength direction. As the curve rises (that is, as the vertical axis increases), the slope of this tangent line increases. The tangent line drawn at the point where the slope value reaches the maximum (that is, 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. In addition, 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 described above. The tangent line drawn at the point where the value of the slope takes the maximum value, which is closest to the maximum value on the shortest wavelength side, is taken 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 measuring device is not limited to this, and it may be measured by combining a cooling device, a cryogenic container, an excitation light source, and a light receiving device.

[0252] · Lowest excited singlet energy S 1 Lowest excited singlet energy S using a solution (sometimes referred to as the solution method). 1 The measurement methods (which may be referred to as the solution method) are as follows. Prepare a 10 μmol / L toluene solution of the compound to be measured and place it in a quartz cell. Measure the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample at room temperature (300 K). Draw a tangent line to the falling edge on the long wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] of the intersection of the tangent line and the horizontal axis into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S 1 [eV] = 1239.85 / λedge Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer (device name: U3310) manufactured by Hitachi.

[0253] The tangent line to the falling edge 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 spectrum curve in the long wavelength direction from the maximum value on the longest wavelength side, consider the tangent line at each point on the curve. This tangent line repeatedly decreases and then increases as the curve falls (that is, as the value on the vertical axis decreases). The tangent line drawn at the point where the value of the slope takes the minimum value on the longest wavelength side (excluding the case where the absorbance is 0.1 or less) is taken as the tangent line to the falling edge on the long wavelength side of the absorption spectrum. Note that the maximum points with absorbance values of 0.2 or less are not included in the maximum value on the longest wavelength side described above.

[0254] [Third Embodiment] (Material for Organic Electroluminescence Element) The material for an organic electroluminescence element according to the third embodiment contains the compound according to the above embodiment (the first embodiment or the second embodiment). The material for an organic electroluminescence element may be abbreviated as the material for an organic EL element. As one aspect, a material for an organic EL element containing only the compound according to the first embodiment can be mentioned. As another aspect, a material for an organic EL element containing the compound according to the first embodiment and another compound different from the compound in the first embodiment can be mentioned. Also, as one aspect, a material for an organic EL element containing only the compound according to the second embodiment can be mentioned. As another aspect, a material for an organic EL element containing the compound according to the second embodiment and another compound different from the compound in the second embodiment can be mentioned. In the material for an organic EL element of the third embodiment, it is preferable that the compound according to the above embodiment is a host material. In this case, the material for an organic EL element may contain the compound according to the above embodiment as a host material and other compounds such as a dopant material. Also, in the material for an organic EL element of the third embodiment, it is preferable that the compound according to the above embodiment is a thermally activated delayed fluorescence material.

[0255] [Fourth Embodiment] (Organic Electroluminescence Element) The organic EL element according to the fourth embodiment will be described. The organic EL element according to the fourth embodiment includes an organic layer between both electrodes of an anode and a cathode. 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.

[0256] The organic EL element according to the fourth embodiment has an anode, a cathode, and an organic layer, and the organic layer contains the compound according to the first embodiment or the second embodiment as a first compound.

[0257] In the organic EL element according to the fourth embodiment, the organic layer preferably has at least one light-emitting layer, and the light-emitting layer contains the compound according to the first embodiment or the second embodiment as a first compound.

[0258] The organic layer may be composed of, for example, a single light-emitting layer, or may contain layers that can be employed in the organic EL element. The layers that can be employed in the organic EL element 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 barrier layer, a hole barrier layer, an electron transport layer, and an electron injection layer.

[0259] 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.

[0260] Fig. 3 shows a schematic configuration of an example of the organic EL element according to the fourth embodiment. The organic EL element 1 includes a light-transmissive 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. 3.

[0261] (Light-emitting layer) In the organic EL element of the fourth embodiment, the light-emitting layer contains a first compound and a second compound. The first compound in the light-emitting layer is preferably a compound according to the first embodiment or the second embodiment. In this case, the first compound is preferably a host material (sometimes referred to as a matrix material), and the second compound is also preferably a dopant material (sometimes referred to as a guest material, an emitter, or a light-emitting material). In the fourth embodiment, when the light-emitting layer contains a compound according to the first embodiment or the second 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.

[0262] (First compound) The first compound is a compound according to the first embodiment or the second embodiment. The first compound of the fourth embodiment is preferably a compound having thermally activated delayed fluorescence properties.

[0263] (Second compound) The second compound is preferably a fluorescent compound. The second compound is preferably a compound that does not exhibit thermally activated delayed fluorescence properties. The second compound of the fourth embodiment is not a phosphorescent metal complex. The second compound is preferably not a heavy metal complex. Also, the second compound is preferably not a metal complex.

[0264] As the second compound of the fourth embodiment, a fluorescent material can be used. Specific examples of the fluorescent material include, for example, bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyromethene boron complex compounds, compounds having a pyromethene skeleton, metal complexes of compounds having a pyromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0265] The second compound is preferably a compound that exhibits emission with a maximum peak wavelength of 400 nm or more and 700 nm or less. In this specification, the maximum peak wavelength refers to the peak wavelength of the fluorescence spectrum measured for a toluene solution in which the compound to be measured is dissolved at a concentration of 10 -6 mol / liter or more and 10 -5 mol / liter or less, at which the emission intensity in the measured fluorescence spectrum is maximum. The measuring device uses a spectrofluorophotometer (manufactured by Hitachi High-Tech Science Corporation, F-7000).

[0266] The second compound preferably exhibits red emission or green emission. In this specification, red emission refers to emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 600 nm or more and 660 nm or less. When the second compound is a red fluorescent compound, the maximum peak wavelength of the second compound is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and still more preferably 610 nm or more and 630 nm or less. In this specification, green emission refers to emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 500 nm or more and 560 nm or less. When the second compound is a green fluorescent compound, the maximum peak wavelength of the second compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and still more preferably 510 nm or more and 540 nm or less. In this specification, blue light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 430 nm or more and 480 nm or less. When the second compound is a blue fluorescent compound, the maximum peak wavelength of the second compound is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

[0267] The measurement of the maximum peak wavelength of the light emitted from the organic EL element is performed as follows. The voltage is applied to the organic EL element so that the current density is 10 mA / cm 2 The spectral radiance spectrum at this time is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is measured, and this is taken as the maximum peak wavelength (unit: nm).

[0268] (Compound represented by general formula (D1)) In the fourth embodiment, it is also preferable that the second compound is a compound represented by the following general formula (D1).

[0269]

Chemical formula

[0270] (In the general formula (D1), Ring Ax, ring Bx, ring Dx, ring Ex and ring Fx are each independently A substituted or unsubstituted aryl ring having 6 to 30 ring-forming carbon atoms, and A substituted or unsubstituted heterocyclic ring having 5 to 30 ring-forming atoms is a ring structure selected from the group consisting of, Either ring Bx or ring Dx exists, or both rings Bx and Dx exist, When both rings Bx and Dx exist, rings Bx and Dx share a bond connecting Zc and Zh, Either ring Ex or ring Fx exists, or both rings Ex and Fx exist, When both rings Ex and Fx exist, rings Ex and Fx share a bond connecting Zf and Zi, Za is a nitrogen atom or a carbon atom, Zb is, When ring Bx exists, it is a nitrogen atom or a carbon atom, When ring Bx does not exist, it is an oxygen atom, a sulfur atom, NRb, C(Rb 1 )(Rb 2 ) or Si(Rb 3 )(Rb 4 ), Zc is a nitrogen atom or a carbon atom, Zd is, When ring Dx exists, it is a nitrogen atom or a carbon atom, When ring Dx does not exist, it is an oxygen atom, a sulfur atom or NRd, Ze is, When ring Ex exists, it is a nitrogen atom or a carbon atom, When ring Ex does not exist, it is an oxygen atom, a sulfur atom or NRe, Zf is a nitrogen atom or a carbon atom, Zg is, When ring Fx exists, it is a nitrogen atom or a carbon atom, When ring Fx does not exist, it is an oxygen atom, a sulfur atom, NRg, C(Rg 1 )(Rg 2 ) or Si(Rg 3 )(Rg 4 ), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb, Rb 1 , Rb 2 , Rb 3, Rb 4 , Rd, Re, Rg, Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are each independently a hydrogen atom or a substituent, Rb as a substituent, Rb 1 , Rb 2 , Rb 3 , Rb 4 , Rd, Re, Rg, Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, -Si(R 911 )(R 912 )(R 913 )-represented group, -O-(R 914 )-represented group, -S-(R 915 )-represented group, or -N(R 916 )(R 917 )-represented group, and however, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds. )

[0271] In the second compound, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds, and this single bond is a covalent bond, not a coordination bond.

[0272] In this specification, examples of the heterocyclic ring include, for example, the ring structure (heterocyclic ring) obtained by removing the bond from the "heterocyclic group" exemplified in the "substituents described in this specification" above. These heterocyclic rings may or may not have substituents. In this specification, examples of the aryl ring include a ring structure (aryl ring) obtained by removing a bond from the "aryl group" exemplified by the "substituents described in this specification" mentioned above. These aryl rings may or may not have substituents.

[0273] (Compound represented by general formula (D11)) In the organic EL element according to the fourth embodiment, it is also preferable that the second compound is a compound represented by the following general formula (D11). It is also preferable that the compound represented by the general formula (D1) is a compound represented by the following general formula (D11).

[0274] [Chemical formula]

[0275] (In the general formula (D11), ring Ax, ring Dx and ring Ex are each independently a substituted or unsubstituted aryl ring having 6 to 30 ring-forming carbon atoms, and a substituted or unsubstituted heterocyclic ring having 5 to 30 ring-forming atoms and are ring structures selected from the group consisting of Za is a nitrogen atom or a carbon atom, Zb is an oxygen atom, a sulfur atom, NRb, C(Rb 1 )(Rb 2 ) or Si(Rb 3 )(Rb 4 ), Zc is a nitrogen atom or a carbon atom, Zd is a nitrogen atom or a carbon atom, Ze is a nitrogen atom or a carbon atom, Zf is a nitrogen atom or a carbon atom, Zg is an oxygen atom, a sulfur atom, NRg, C(Rg 1 )(Rg 2 ) or Si(Rg 3 )(Rg 4 ), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb, Rb 1 , Rb 2 , Rb 3 , Rb 4 , Rg, Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are each independently synonymous with Rb, Rb 1 , Rb 2 , Rb 3 , Rb 4 , Rg, Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh in the general formula (D1).)

[0276] (Compound represented by the general formula (D10)) In the organic EL element according to the fourth embodiment, it is also preferable that the second compound is a compound represented by the following general formula (D10). It is also preferable that the compound represented by the general formula (D1) is a compound represented by the following general formula (D10).

[0277]

Chemical formula

[0278] (In the general formula (D10), X 1 is CR 1 or a nitrogen atom, X 2 is CR 2 or a nitrogen atom, X 3 is CR 3 or a nitrogen atom, X 4 is CR 4 or a nitrogen atom, X 5 is CR 5 or a nitrogen atom, X6 is CR 6 or a nitrogen atom, X 7 is CR 7 or a nitrogen atom, or X 8 is a carbon atom bonded to it by a single bond, X 8 is CR 8 or a nitrogen atom, or X 7 is a carbon atom bonded to it by a single bond, X 9 is CR 9 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 ), R 1 ~R 6 and one or more sets of two or more adjacent ones of R 9 ~R 11 are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other, R 3、 R 4 and R Y1 and one or more sets of two or more adjacent ones of R are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or not bonded to each other, R 3、 R 4 and R Y1 at least one hydrogen in a monocyclic or condensed ring formed by combining one or more sets of two or more adjacent ones among them 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 a group represented by -N(R 921 )(R 922 ), and is substituted with at least any substituent selected from the group consisting of these groups, 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, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 1 ~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, a group represented by -Si(R 911 )(R 912 )(R 913 ), a group represented by -O-(R 914 ), a group represented by -S-(R 915 ), a group represented by -N(R 916 )(R 917 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 918 a group represented by -COOR 919 a 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, and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned 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, and 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 above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned 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, and R 911 ~R922 is, independently of each other, 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's exist, the plurality of R's 911 are the same as or different from each other, R 912 When a plurality of R's exist, the plurality of R's 912 are the same as or different from each other, R 913 When a plurality of R's exist, the plurality of R's 913 are the same as or different from each other, R 914 When a plurality of R's exist, the plurality of R's 914 are the same as or different from each other, R 915 When a plurality of R's exist, the plurality of R's 915 are the same as or different from each other, R 916 When a plurality of R's exist, the plurality of R's 916 are the same as or different from each other, R 917 When a plurality of R's exist, the plurality of R's 917 are the same as or different from each other, R 918 When a plurality of R's exist, the plurality of R's 918 are the same as or different from each other, R 919 When a plurality of R's exist, the plurality of R's 919 are the same as or different from each other, R 920 When a plurality of R's exist, the plurality of R's 920 are the same as or different from each other, R 921 When a plurality of R's exist, the plurality of R's 921 are the same as or different from each other, R922 When there are a plurality of R's 922 they may be the same as or different from each other.)

[0279] In the compound represented by the general formula (D10), X 7 is a carbon atom bonded to X 8 by a single bond, and when X 8 is a carbon atom bonded to X 7 by a single bond, for example, the general formula (D10) is represented by the following general formula (D10A).

[0280]

Chemical formula

[0281] (In the general formula (D10A), X 1 ~X 6 , X 9 ~X 12 , Y, Q, and R 13 are each independently as defined in the general formula (1).)

[0282] The compound represented by the general formula (D10) is preferably represented by the following general formula (D12).

[0283]

Chemical formula

[0284] (In the general formula (D12), R 1 ~R 13 , R Y1 , R Q are each independently as defined in the general formula (D10).)

[0285] The compound represented by the general formula (D10) is preferably represented by the following general formula (D12A).

[0286]

Chemical formula

[0287] (In the general formula (D12A), R 1 ~R 6 , R 9 ~R 13 , R Y1 , R Q are each independently as defined in the general formula (D10).)

[0288] It is also preferable that the compound represented by the general formula (D10) is represented by the following general formula (D13).

[0289]

Chemical formula

[0290] (In the general formula (D13), R 1 ~R 3 , R 5 ~R 13 and R Q are each independently as defined in the general formula (D10), R x1 ~R x4 One or more sets of two or more adjacent ones among them are combined with each other to form a substituted or unsubstituted monocyclic ring, combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, 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 ~R 939 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 heterocyclic group having 5 to 50 ring-forming atoms, R 931 When there are a plurality of R 931 are the same as or different from each other, R 932 When there are a plurality of R 932 are the same as or different from each other, R 933 When there are a plurality of R 933 are the same as or different from each other, R 934 When there are a plurality of R 934 are the same as or different from each other, R 935 When there are a plurality of R935 are the same as or different from each other, R 936 when there are a plurality of R's, the plurality of R's 936 are the same as or different from each other, R 937 when there are a plurality of R's, the plurality of R's 937 are the same as or different from each other, R 938 when there are a plurality of R's, the plurality of R's 938 are the same as or different from each other, R 939 when there are a plurality of R's, the plurality of R's 939 are the same as or different from each other.)

[0291] In the general formula (D13), for example, a pair consisting of R 5 and R 6 either combines with each other to form a substituted or unsubstituted monocyclic ring, combines with each other to form a substituted or unsubstituted condensed ring, or does not combine with each other.

[0292] The compound represented by the general formula (D10) is preferably represented by the following general formula (D13A).

[0293]

Chemical formula

[0294] (In the general formula (D13A), R 1 ~R 3 , R 5 ~R 6 , R 9 ~R 13 and R Q are each independently as defined in the general formula (1), and R x1 ~R x4 are each independently as defined in the general formula (D13).)

[0295] In the compound represented by the general formula (D10), R 1 ~R 13 and RQ 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 heteroaryl group having 5 to 50 ring-forming atoms is also preferred.

[0296] In the compound represented by the general formula (D10), R 1 ~R 13 and R Q are, independently of each other, 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.

[0297] In the compound represented by the general formula (D10), R 1 ~R 3 、R 5 ~R 13 、R Q and R x1 ~R x4 are, 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 heteroaryl group having 5 to 50 ring-forming atoms is also preferred.

[0298] In the compound represented by the general formula (D10), R 1 ~R 3 、R 5 ~R 13 、R Q and R x1 ~R x4 are, independently of each other, 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 it is also preferable that it is a substituted or unsubstituted heteroaryl group having 5 to 25 ring-forming atoms.

[0299] In the compound represented by the general formula (D10), R 1 ~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 it is preferably a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms.

[0300] In the compound represented by the general formula (D10), R 1 ~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 it is preferably a substituted or unsubstituted heteroaryl group having 5 to 25 ring-forming atoms.

[0301] It is also preferable that the compound represented by the general formula (D10) is represented by the following general formula (D14).

[0302]

Chemical formula

[0303] (In the general formula (D14), R 2 、R 6、 R 13、 R Q and R x2are 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.)

[0304] The compound represented by the general formula (D10) is preferably represented by the following general formula (D15).

[0305]

Chemical formula

[0306] (In the general formula (D15), R 2 , 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.)

[0307] In the compound represented by the general formula (D10), 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.)

[0308] In the compound represented by the general formula (D10), R 6 and R x2is preferably, independently of each other, a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0309] (Compound represented by general formula (D20)) In the organic EL element according to the fourth embodiment, it is also preferable that the second compound is a compound represented by the following general formula (D20).

[0310] [Chemical formula]

[0311] In the general formula (D20), X is a nitrogen atom or a carbon atom bonding to Y, Y is a hydrogen atom or a substituent, R 21 ~R 26 are each independently a hydrogen atom or a substituent, or a combination of R 21 and R 22 of the combination of R 22 and R 23 of the combination of R 24 and R 25 of the combination of R 25 and R 26 of any one or more of the combinations are bonded to each other to form a ring, Y as a substituent, and R 21 ~R 26 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl 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 aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, A halogen atom, A carboxy group, A substituted or unsubstituted ester group, A substituted or unsubstituted carbamoyl group, A substituted or unsubstituted amino group, A nitro group, A cyano group, A substituted or unsubstituted silyl group, and Is selected from the group consisting of a substituted or unsubstituted siloxanyl group, Z 21 And Z 22 Are each independently a substituent, or Z 21 And Z 22 Are bonded to each other to form a ring, Z as a substituent 21 And Z 22 Are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and Is selected from the group consisting of a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms.

[0312] In the second compound according to the fourth 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) 2 R 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 An unsubstituted heterocyclic group having 5 to 25 ring-forming atoms, 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.

[0313] In the second compound according to the fourth 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 preferable.

[0314] In the second compound according to the fourth 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 preferable.

[0315] In the second compound according to the fourth embodiment, it is also preferable that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0316] (Specific examples of the compound represented by general formula (D1), (D11), (D10) or (D20)) Specific examples of the compound represented by the general formula (D1), (D11), (D10) or (D20) include, for example, the following compounds. However, the present invention is not limited to these specific examples.

[0317]

Chemical formula

[0318]

Chemical formula

[0319]

Chemical formula

[0320]

Chemical formula

[0321]

Chem.

[0322]

Chem.

[0323]

Chem.

[0324]

Chem.

[0325]

Chem.

[0326]

Chem.

[0327]

Chem.

[0328]

Chem.

[0329]

Chem.

[0330]

Chem.

[0331] [Chemical formula]

[0332] Note that the coordination bond between the boron atom and the nitrogen atom in the pyromethene skeleton can be represented by various notations, such as solid lines, dashed lines, arrows, or omission. In this specification, it is represented by a solid line, a dashed line, or the description is omitted.

[0333] [Chemical formula]

[0334] [Chemical formula]

[0335] [Chemical formula]

[0336] [Chemical formula]

[0337] [Chemical formula]

[0338] [Chemical formula]

[0339] [Chemical formula]

[0340] (Relationship between the first compound and the second compound in the light-emitting layer) In the organic EL element according to the fourth embodiment, the light-emitting layer contains a first compound and further a second compound. The second compound is a fluorescent compound, and the singlet energy S 1 (M1) of the first compound and the singlet energy S 1 (M2) of the second compound preferably satisfy the relationship of the following formula (Formula 1). S 1 (M1)>S 1 (M2) …(Formula 1)

[0341] The energy gap T 77K (M1) of the first compound at 77 [K] is preferably larger than the energy gap T 77K (M2) of the second compound at 77 [K]. That is, it preferably satisfies the relationship of the following formula (Formula 5). T 77K (M1)>T 77K (M2)…(Formula 5)

[0342] When the organic EL element of the fourth embodiment emits light, it is preferable that mainly the second compound emits light in the light-emitting layer.

[0343] (TADF mechanism) FIG. 4 is a diagram showing an example of the relationship between the energy levels of the second compound M2 and the first compound M1 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(M1) to S1(M2) in FIG. 4 represents Förster-type energy transfer from the lowest excited singlet state of the first compound M1 to the second compound M2. As shown in Fig. 4, when a compound with a small ΔST(M1) is used as the first compound M1, the lowest excited triplet state T1(M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) by thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M1) of the first compound M1 to the second compound M2, generating the lowest excited singlet state S1(M2). As a result, fluorescence emission from the lowest excited singlet state S1(M2) of the second compound M2 can be observed. It is also considered that the internal quantum efficiency can be theoretically increased up to 100% by utilizing the delayed fluorescence based on this TADF mechanism.

[0344] The organic EL element of the fourth embodiment preferably emits red light or green light. When the organic EL element of the fourth embodiment emits green light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less. When the organic EL element of the fourth embodiment emits red light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 600 nm or more and 660 nm or less. When the organic EL element of the fourth embodiment emits blue light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less.

[0345] The measurement of the maximum 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 becomes 10 mA / cm 2 is measured with a spectro-radiometer 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 maximum peak wavelength (unit: nm).

[0346] (Thickness of the light-emitting layer) In the organic EL element of the fourth embodiment, the film thickness of the light-emitting layer is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and most preferably 10 nm or more and 50 nm or less. When it is 5 nm or more, it becomes easier to form the light-emitting layer and adjust the chromaticity. When it is 50 nm or less, an increase in the driving voltage is likely to be suppressed.

[0347] (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 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. Also, the content ratio of the first compound may be 90% by mass or more and 99.9% by mass or less, may be 95% by mass or more and 99.9% by mass or less, or may be 99% by mass or more and 99.9% by mass or less. The content ratio of the second compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. Note that the fourth embodiment does not exclude the case where materials other than the first compound and the second compound are included in the light-emitting layer. The light-emitting layer may contain only one kind of the first compound or may contain two or more kinds. The light-emitting layer may contain only one kind of the second compound or may contain two or more kinds.

[0348] (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.

[0349] (Anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), 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 zinc oxide can be formed by a sputtering method by 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, tungsten oxide and indium oxide containing zinc oxide can be formed by a sputtering method by 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 a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, etc. 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, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these 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, an inkjet method, or the like can be used.

[0350] (Cathode) For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, and a mixture thereof, etc. with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. When forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Also, when using a silver paste or the like, a coating method, an inkjet method, or the like can be used. By providing an electron injection layer, regardless of the work function, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium tin oxide containing silicon or silicon oxide. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, or the like.

[0351] (Hole injection layer) The positive hole injection layer is a layer containing a substance with high positive hole injection property. As substances with high positive hole injection property, 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, as substances with high positive hole injection property, 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. can also be mentioned. In addition, as a substance with high hole injection property, a polymer compound (such as oligomer, dendrimer, polymer, etc.) can also be used. For example, polymer 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 mentioned. Also, polymer 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.

[0352] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport property. For 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. For the hole transport layer, carbazole derivatives such as CBP, CzPA, and PCzPA, and anthracene derivatives such as t-BuDNA, DNA, and DPAnth may 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 the substance has higher hole transportability than electrons, substances other than these may be used. Note that the layer containing a substance with high hole transportability may be a single layer or a layer in which two or more layers made of the above substances are laminated.

[0353] (Electron transport layer) The electron transport layer is a layer containing a substance with high electron transportability. 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: Almq 3 )), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq 2 )), BAlq, Znq, ZnPBO, ZnBTZ, etc. 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-(ptert-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), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. The substances described here are mainly 10-6 cm 2 It is a substance having an electron mobility of / Vs or more. Note that, as long as it is a substance having higher electron transport property than hole transport property, substances other than the above may 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 made of the above substances are laminated. In addition, a high molecular compound 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.

[0354] (Electron injection layer) The electron injection layer is a layer containing a substance having high electron injection property. 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 (CaF 2 )), lithium oxide (LiOx), etc. can be used. In addition, those obtained by incorporating an alkali metal, an alkaline earth metal, or their compounds into a substance having electron transport property, 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 transport 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. As the electron donor, any substance that exhibits electron donating properties to the organic compound may be used. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples include lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Also, alkali metal oxides and alkaline earth metal oxides are preferable, and examples include lithium oxide, calcium oxide, barium oxide, etc. Further, a Lewis base such as magnesium oxide can also be used. Also, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can be used.

[0355] (Layer formation method) As the method for forming each layer of the organic EL element of the fourth embodiment, it is not limited except as specifically mentioned above, and known methods such as dry film formation methods such as vacuum evaporation method, sputtering method, plasma method, ion plating method, and wet film formation methods such as spin coating method, dipping method, flow coating method, inkjet method, etc. can be adopted.

[0356] (Film thickness) The film thickness of each organic layer of the organic EL element of the fourth 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, and conversely, if it is too thick, a high applied voltage is required and the efficiency deteriorates. Therefore, usually, a range of several nm to 1 μm is preferable.

[0357] The organic EL element according to the fourth embodiment includes, in the light emitting layer, a compound according to the first embodiment or the second embodiment as the first compound, and a second compound having a lowest excited singlet energy smaller than that of the first compound. Since the organic EL element according to the fourth embodiment contains the compound (first compound) according to the first embodiment, according to the fourth embodiment, the luminous efficiency of the organic EL element can be improved. Since the organic EL element according to the fourth embodiment contains the compound (first compound) according to the second embodiment, according to the fourth embodiment, the lifetime of the organic EL element can be improved. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0358] 〔Fifth Embodiment〕 The configuration of the organic EL element according to the fifth embodiment will be described. In the description of the fifth embodiment, the same components as those in the fourth embodiment will be given the same reference numerals or names, and the description will be omitted or simplified. Also, in the fifth embodiment, for materials and compounds not particularly mentioned, materials and compounds similar to those described in the fourth embodiment can be used.

[0359] The organic EL element according to the fifth embodiment is different from the organic EL element according to the fourth embodiment in that the light-emitting layer further contains a third compound. Other points are the same as those in the fourth embodiment. That is, in the fifth embodiment, the light-emitting layer contains a first compound, a second compound, and a third compound. In this case, the first compound is preferably a host material, and the second compound is preferably a dopant material.

[0360] (Third Compound) In the light-emitting layer of the organic EL element of the fifth embodiment, the third compound may be a thermally activated delayed fluorescence compound or a compound that does not exhibit thermally activated delayed fluorescence, but it is preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0361] As the third compound, although not particularly limited, it is preferably a compound other than an amine compound. 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.

[0362] (Compound represented by general formula (3)) In the light-emitting layer of the organic EL element of the fifth embodiment, it is also preferable that the third compound is a compound represented by the following general formula (3).

[0363] [Chemical formula]

[0364] (In the general formula (3), A 3 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, L 3 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, a divalent group formed by bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, or a divalent group formed by bonding of three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, R 31 ~R 38 One or more sets of two or more adjacent ones among 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 not bonded to each other, R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 group represented by -COOR 909 group represented by a halogen atom, a cyano group, a nitro group, -P(=O)(R 931 )(R 932 ) group represented by -Ge(R 933 )(R 934 )(R 935 ) group represented by -B(R 936 )(R 937 ) group represented by a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the following general formula (3A).)

[0365] [Chemical]

[0366] (In the general formula (3A), R B is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 )-represented group, -O-(R 904 )-represented group, -S-(R 905 )-represented group, -N(R 906 )(R 907 )-represented group, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 )-represented group, -COOR 909 )-represented group, a halogen atom, a cyano group, a nitro group, -P(=O)(R 931 )(R 932 )-represented group, -Ge(R 933 )(R 934 )(R 935 )-represented group, -B(R 936 )(R 937 )-represented 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 B when a plurality of R's exist, the plurality of R's B are the same as or different from each other, L 31 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the heterocyclic group, or a divalent group formed by bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group, L 32 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, n 3 is 1, 2, 3, 4 or 5, L 31 when is a single bond, n 3 is 1, and L 32 is bonded to a carbon atom of the six-membered ring in the general formula (3), L 32 when a plurality of L's exist, the plurality of L's 32 are the same as or different from each other, * is a bonding site with a carbon atom of the six-membered ring in the general formula (3).)

[0367] (In the compound represented by the general formula (3), R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 901 When there are a plurality of R's, the plurality of R's 901 are the same as or different from each other, R 902 When there are a plurality of R's, the plurality of R's 902 are the same as or different from each other, R 903 When there are a plurality of R's, the plurality of R's 903 are the same as or different from each other, R 904 When there are a plurality of R's, the plurality of R's 904 are the same as or different from each other, R 905 When there are a plurality of R's, the plurality of R's 905 are the same as or different from each other, R 906 When there are a plurality of R's, the plurality of R's 906 are the same as or different from each other, R 907 When there are a plurality of R's, the plurality of R's 907 are the same as or different from each other, R 908 When there are a plurality of R's, the plurality of R's 908 are the same as or different from each other, R 909 When there are a plurality of R's, the plurality of R's 909 are the same as or different from each other, R931 When there are a plurality of them, the plurality of Rs 931 are the same as or different from each other, R 932 When there are a plurality of them, the plurality of Rs 932 are the same as or different from each other, R 933 When there are a plurality of them, the plurality of Rs 933 are the same as or different from each other, R 934 When there are a plurality of them, the plurality of Rs 934 are the same as or different from each other, R 935 When there are a plurality of them, the plurality of Rs 935 are the same as or different from each other, R 936 When there are a plurality of them, the plurality of Rs 936 are the same as or different from each other, R 937 When there are a plurality of them, the plurality of Rs 937 are the same as or different from each other.)

[0368] It is also preferable that the compound represented by the general formula (3) is a compound represented by any one of the following general formulas (31) to (36).

[0369]

Chemical formula

[0370]

Chemical formula

[0371]

Chemical formula

[0372] (In the general formulas (31) to (36), A 3 and L 3 are, respectively, A in the general formula (3) 3 and L3 is synonymous with R 341 ~R 350 one or more sets of two or more adjacent ones among are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, X 31 is a sulfur atom, an oxygen atom, NR 352 or CR 353 R 354 and R 353 and R 354 the set 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 fused 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 fused ring, and R 341 ~R 350 and R 352 and R which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring 353 and R 354 are each independently R which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring 31 ~R 38 is synonymous with.)

[0373] In the compound represented by the general formula (3), R 352 is 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, preferably.

[0374] In the compound represented by the general formula (3), R 353 and R 354A group consisting of combines with each other to form a substituted or unsubstituted monocyclic ring, or combines with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, R 353 and R 354 are each independently 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, preferably.

[0375] In the compound represented by the general formula (3), X 31 is preferably a sulfur atom or an oxygen atom.

[0376] In the compound represented by the general formula (3), A 3 is preferably a group represented by any one of the following general formulas (A31) to (A37).

[0377]

Chemical formula

[0378]

Chemical formula

[0379] (In the general formulas (A31) to (A37), one or more sets of two or more adjacent ones among a plurality of R 300 combine with each other to form a substituted or unsubstituted monocyclic ring, or combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 300 , and R 333 are each independently R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 and have the same meaning as, * in the general formulas (A31) to (A37) each indicates the bonding position of the compound represented by the general formula (3) with L 3 .)

[0380] In the compound represented by the general formula (3), it is also preferable that A 3 is a group represented by the general formula (A34), (A35) or (A37).

[0381] It is also preferable that the compound represented by the general formula (3) is a compound represented by any of the following general formulas (311) to (316).

[0382] [Chemical formula]

[0383] [Chemical formula]

[0384] [Chemical formula]

[0385] [Chemical formula]

[0386] [Chemical formula]

[0387] [Chemical formula]

[0388] (In the general formulas (311) to (316), L 3 is synonymous with L in the general formula (3), 3 and one or more sets of two or more adjacent ones among the plurality of Rs are bonded to each other to form a substituted or unsubstituted monocyclic ring, 300 or are bonded to each other to form a substituted or unsubstituted condensed ring, or do not bond to each other, and one or more sets of two or more adjacent ones among the Rs ~R R 341 ~R 350 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, or do not bond to each other, and the R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, and the R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, 300 and the R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, 341 ~R 350 are each independently synonymous with the R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, 31 ~R 38 .)

[0389] It is also preferable that the compound represented by the general formula (3) is a compound represented by the following general formula (321).

[0390]

Chemical formula

[0391] (In the general formula (321), L 3 is synonymous with L in the general formula (3),3 is synonymous with, R 31 ~R 38 , and R 301 ~R 308 does not independently form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, respectively. R 31 ~R 38 is synonymous with.)

[0392] In the compound represented by the general formula (3), L 3 is preferably a single bond or an arylene group having 6 to 50 ring-forming carbon atoms which may be substituted or unsubstituted.

[0393] In the compound represented by the general formula (3), L 3 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group is preferable.

[0394] In the compound represented by the general formula (3), L 3 is preferably a group represented by the following general formula (317).

[0395]

Chemical formula

[0396] (In the general formula (317), R 310 does not independently form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, respectively. R 31 ~R 38 is synonymous with, and * independently indicates the bonding position.)

[0397] In the compound represented by the general formula (3), L 3It is also preferable that it contains a divalent group represented by the following general formula (318) or general formula (319). In the compound represented by the general formula (3), L 3 is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0398] The compound represented by the general formula (3) is also preferably a compound represented by the following general formula (322) or general formula (323).

[0399]

Chemical formula

[0400]

Chemical formula

[0401] (In the general formula (322) and general formula (323), L 31 is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, provided that L 31 contains a divalent group represented by the following general formula (318) or general formula (319), R 31 ~R 38 , R 300 , and R 321 ~R 328 are each independently the same as R 31 ~R 38 which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring.)

[0402]

Chemical formula

[0403] (In the general formula (319), a pair consisting of two adjacent ones among the plurality of Rs 304 are bonded to each other to form a ring represented by the general formula (320), in the general formula (320), 1* and 2* each independently indicate the bonding position with the ring to which R 304 is bonded, R in the general formula (318) 302 , R in the general formula (318) 303 , R in the general formula (319) 303 , R that does not form the ring represented by the general formula (320) 304 , and R in the general formula (320) 305 are each independently R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 and have the same meaning as * in the general formulas (318) to (320) each indicates the bonding position.)

[0404] In the compound represented by the general formula (3), the group represented by the general formula (319) as L 3 or L 31 is, for example, a group represented by the following general formula (319A).

[0405] [Chemical formula]

[0406] (In the general formula (319A), R 303 , R 304 and R 305 are each independently R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38is synonymous, and * in the general formula (319A) indicates the bonding position respectively.

[0407] The compound represented by the general formula (3) is the compound represented by the general formula (322), and L 31 is preferably a group represented by the general formula (318).

[0408] The compound represented by the general formula (3) is preferably a compound represented by the following general formula (324).

[0409]

Chemical formula

[0410] (In the general formula (324), R 31 ~R 38 , R 300 , and R 302 are each independently R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 is synonymous.)

[0411] In the compound represented by the general formula (3), R 31 ~R 38 that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the general formula (3A), and R B in the general formula (3A) is 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

[0412] In the compound represented by the general formula (3), R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a group represented by the general formula (3A), R in the general formula (3A) B is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[0413] In the compound represented by the general formula (3), R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a group represented by the general formula (3A), R in the general formula (3A) B is preferably a substituted or unsubstituted phenyl group.

[0414] It is also preferable that the compound represented by the general formula (3) is a compound having no pyridine ring, pyrimidine ring, and triazine ring.

[0415] (Compound represented by the general formula (MRX3)) In the light-emitting layer of the organic EL element of the fifth embodiment, it is also preferable that the third compound is a compound represented by the following general formula (MRX3).

[0416]

Chemical formula

[0417] (In the general formula (MRX3), Y 31 ~Y 36 each independently represents CR 3 or a nitrogen atom, provided that two or more of Y 31 ~Y 36 are nitrogen atoms, R 3 When there are a plurality of R 3 one or more sets of two or more adjacent ones among the plurality of R 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 do not bond to each other, do not form the substituted or unsubstituted monocyclic ring, and do not form the substituted or unsubstituted condensed ring, and R 3 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 group represented by, -COOR 909 group represented by, a halogen atom, a cyano group, a nitro group, -P(=O)(R 931 )(R 932 )-represented group, -Ge(R 933 )(R 934 )(R 935 )-represented group, -B(R 936 )(R 937 )-represented group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or a group represented by the following general formula (MRX3A).)

[0418]

Chemical formula

[0419] (In the general formula (MRX3A), R B has the same meaning as R B in the general formula (3), R B When there are a plurality of R B are the same as or different from each other, L 31 and L 32 each have the same meaning as L 31 and L 32 in the general formula (3), n 3 is 1, 2, 3, 4 or 5, L 31 When is a single bond, n 3 is 1, and L 32 is bonded to the carbon atom of the six-membered ring in the general formula (MRX3), L 32 When there are a plurality of L 32 are the same as or different from each other, * is the bonding site with the carbon atom of the six-membered ring in the general formula (MRX3).)

[0420] The compound represented by the general formula (MRX3) preferably does not contain a pyridine ring in the molecule.

[0421] The compound represented by the general formula (MRX3) is also preferably a compound represented by the following general formula (MRX31) or general formula (MRX32).

[0422] [Chemical formula]

[0423] (In the general formula (MRX32), R 35 ~R 37 One or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R in the general formula (MRX31) 31 ~R 33 , and R in the general formula (MRX32) 34 and the R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 35 ~R 37 are each independently synonymous with R in the general formula (MRX3).) 3

[0424] The compound represented by the general formula (MRX3) is also preferably a compound represented by the general formula (MRX31).

[0425] R in the general formula (MRX3) 3 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, or It is preferably a group represented by the general formula (MRX3A).

[0426] R in the general formula (MRX3) 3 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 It is preferably a group represented by the general formula (MRX3A).

[0427] The compound represented by the general formula (MRX3) preferably has at least one group selected from the group consisting of groups represented by the following general formulas (MRXA31) to (MRXA44) in the molecule.

[0428]

Chemical formula

[0429]

Chemical formula

[0430] (In the general formulas (MRXA31) to (MRXA38), two or more adjacent pairs of a plurality of R 300 are combined with each other to form a substituted or unsubstituted monocyclic ring, are combined with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, a pair consisting of R R 331 and R 332 is combined with each other to form a substituted or unsubstituted monocyclic ring, is combined 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 of R ​300 , R 331 and R 332 , and R 333 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by, -O-(R 904 ) group represented by, -S-(R 905 ) group represented by, -N(R 906 )(R 907 ) group represented by, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 group represented by, -COOR 909 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, and * in the general formulas (MRXA31) to (MRXA38) each indicates the bonding position with other atoms in the molecule of the compound represented by the general formula (MRX3).)

[0431]

Chemical formula

[0432]

Chemical formula

[0433] [Chemical]

[0434] (In the general formulas (MRXA39) to (MRXA44), R 341 ~R 350 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, However, R 341 ~R 351 at least one of them indicates the bonding position with other atoms in the molecule of the compound represented by the general formula (MRX3), X 31 is a sulfur atom, an oxygen atom, NR 352 or CR 353 R 354 and R 353 and R 354 the set consisting of them is 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 at the bonding position with other atoms in the molecule of the compound represented by the general formula (MRX3), and does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, R 341 ~R 351 and R 352 and R 353 and R 354 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by A substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 ) group represented by -COOR 909 ) 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.)

[0435] The compound represented by the general formula (MRX3) preferably has at least one group selected from the group consisting of the groups represented by the general formulas (MRXA38) to (MRXA44) in the molecule.

[0436] In the compound represented by the general formula (MRX3), 31 ~Y 36 At least one of them is CR 3 , At least one R 3 is a group represented by the general formula (MRX3A), and R B is preferably any one of the groups represented by the general formulas (MRXA31) to (MRXA44).

[0437] In the compound represented by the general formula (MRX3), Y 31 ~Y 36 at least one of which is CR 3 and at least one R 3 is a group represented by the general formula (MRX3A), and R B is preferably any one of the groups represented by the general formulas (MRXA38) to (MRXA44).

[0438] In the compound represented by the general formula (MRX3), R 352 is 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, preferably.

[0439] In the compound represented by the general formula (MRX3), R 353 and R 354 the group consisting of either 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 a substituted or unsubstituted monocyclic ring, and do not form a substituted or unsubstituted condensed ring, and R 353 and R 354 are each independently 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, preferably.

[0440] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), L 31 is a single bond, A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, or A divalent group formed by bonding two groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring-forming carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group, L 32 is a single bond, or preferably a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.

[0441] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), L 31 is a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, n 3 is 1, L 32 is a single bond, or preferably a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.

[0442] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), L 31 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted phenylene group and a substituted or unsubstituted biphenylene group, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group, n 3 is 1, L 32 is a single bond, a substituted or unsubstituted phenylene group, or It is preferably a substituted or unsubstituted biphenylene group.

[0443] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), 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 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 ) group represented by -COOR 909 ) group represented by -P(=O)(R 931 )(R 932 ) group represented by -Ge(R 933 )(R 934 )(R 935 ) group represented by -B(R 936 )(R 937 ) group represented by -S(=O) 2 R 938 ) group represented by a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms, R 901 ~R 909 , and R931 ~R 938 is, 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, preferably.

[0444] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), 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, preferably.

[0445] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), 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, preferably.

[0446] In the compound represented by the general formula (3) and the compound represented by the general formula (MRX3), it is also preferable that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0447] (Method for producing the third compound) The third compound according to the fifth embodiment can be produced by a known method.

[0448] (Specific examples of the third compound) Specific examples of the third compound of the present embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples of the compounds.

[0449]

Chem.

[0450]

Chem.

[0451]

Chem.

[0452]

Chem.

[0453]

Chem.

[0454]

Chem.

[0455]

Chem.

[0456]

Chem.

[0457]

Chem.

[0458]

Chem.

[0459]

Chem.

[0460]

Chem.

[0461]

Chem.

[0462]

Chem.

[0463]

Chem.

[0464]

Chem.

[0465]

Chem.

[0466]

Chem.

[0467]

Chem.

[0468]

Chem.

[0469]

Chem.

[0470] [Chemical]

[0471] [Chemical]

[0472] [Chemical]

[0473] [Chemical]

[0474] [Chemical]

[0475] [Chemical]

[0476] [Chemical]

[0477] [Chemical]

[0478] [Chemical]

[0479] [Chemical]

[0480] [Chemical]

[0481]

Chem.

[0482]

Chem.

[0483]

Chem.

[0484]

Chem.

[0485]

Chem.

[0486]

Chem.

[0487]

Chem.

[0488]

Chem.

[0489] (Relationship among the first compound, the second compound, and the third compound in the light-emitting layer) In the organic EL element according to the fifth embodiment, the singlet energy S 1 (M1) of the first compound and the singlet energy S 1 (M3) of the third compound preferably satisfy the relationship of the following formula (Formula 2). S 1 (M3)>S 1 (M1) …(Formula 2)

[0490] In the organic EL element according to the fifth embodiment, the light-emitting layer includes a first compound, a second compound, and a third compound. The second compound is a fluorescent compound, and the singlet energy S 1 (M1) of the first compound, the singlet energy S 1 (M2) of the second compound, and the singlet energy S 1 (M3) of the third compound preferably satisfy the following relational expression (Equation 3). S 1 (M3)>S 1 (M1)>S 1 (M2) …(Equation 3)

[0491] The energy gap T 77K (M3) of the third compound at 77 [K] is preferably larger than the energy gap T 77K (M1) of the first compound at 77 [K]. The energy gap T 77K (M3) of the third compound at 77 [K] is preferably larger than the energy gap T 77K (M2) of the second compound at 77 [K].

[0492] The energy gap T 77K (M1) of the first compound at 77 [K], the energy gap T 77K (M2) of the second compound at 77 [K], and the energy gap T 77K (M3) of the third compound at 77 [K] preferably satisfy the following relational expression (Equation 2B). T 77K (M3)>T 77K (M1)>T 77K (M2) …(Equation 2B)

[0493] When the organic EL element of the fifth embodiment emits light, it is preferable that a fluorescent compound mainly emits light in the light-emitting layer. The organic EL element of the fifth embodiment preferably emits red light or green light, similar to the organic EL element of the fourth embodiment. The maximum peak wavelength of the light emitted from the organic EL element can be measured in the same manner as the organic EL element of the fourth embodiment.

[0494] (Content ratio of the compound in the light-emitting layer) The content ratios of the first compound, the second compound, and the third compound contained in the light-emitting layer are preferably in the following ranges, for example. The content ratio of the first 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 second compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The content 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 the fifth embodiment does not exclude the inclusion of materials other than the first compound, the second compound, and the third compound in the light-emitting layer. The light-emitting layer may contain only one kind of the first compound or two or more kinds. The light-emitting layer may contain only one kind of the second compound or two or more kinds. The light-emitting layer may contain only one kind of the third compound or two or more kinds.

[0495] 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(M1) to S1(M2) in FIG. 5 represents Förster-type energy transfer from the lowest excited singlet state of the first compound to the lowest excited singlet state of the second compound. As shown in FIG. 5, when a compound with a small ΔST(M1) is used as the first compound, the lowest excited triplet state T1(M1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) by thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M1) of the first compound to the second compound, generating the lowest excited singlet state S1(M2). As a result, fluorescence emission from the lowest excited singlet state S1(M2) of the second compound can be observed. It is also considered that the internal quantum efficiency can be theoretically increased to 100% by utilizing the delayed fluorescence based on this TADF mechanism.

[0496] The organic EL element according to the fifth embodiment includes, in the light-emitting layer, a compound according to the first embodiment or the second embodiment as the first compound, a second compound having a lowest excited singlet energy smaller than that of the first compound, and a third compound having a lowest excited singlet energy larger than that of the first compound. Since the organic EL element according to the fifth embodiment includes the compound (first compound) according to the first embodiment, the light-emitting efficiency of the organic EL element can be improved according to the fifth embodiment. Since the organic EL element according to the fifth embodiment includes the compound (first compound) according to the second embodiment, the lifetime of the organic EL element can be improved according to the fifth embodiment. The organic EL element according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0497] 〔Sixth Embodiment〕 The configuration of the organic EL element according to the sixth embodiment will be described. In the description of the sixth embodiment, the same components as those in the fourth embodiment or the fifth embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Further, in the sixth embodiment, for materials and compounds not particularly mentioned, the same materials and compounds as those described in the fourth embodiment or the fifth embodiment can be used.

[0498] The organic EL element according to the sixth embodiment is different from the organic EL element according to the fourth embodiment or the fifth embodiment in that the light-emitting layer contains the first compound and the third compound and does not contain the second compound. Other points are the same as those in the fourth embodiment or the fifth embodiment. That is, in the sixth embodiment, the light-emitting layer as the first organic layer contains the first compound and the third compound. In this case, the third compound is preferably a host material, and the first compound is preferably a dopant material. In the sixth embodiment, when the light-emitting layer contains the compound according to the first embodiment or the second embodiment, it is preferable that the light-emitting layer does not contain a phosphorescent metal complex and does not contain a metal complex other than the phosphorescent metal complex.

[0499] <First Compound> The first compound is the compound according to the first embodiment or the second embodiment. The first compound is preferably a thermally activated delayed fluorescence compound.

[0500] <Third Compound> The third compound is the same as the third compound described in the fifth embodiment.

[0501] (Relationship between the first compound and the third compound in the light-emitting layer) In the organic EL element according to the sixth embodiment, the singlet energy S of the first compound 1 (M1) and the singlet energy S of the third compound 1 (M3) preferably satisfy the relationship of the following formula (Formula 2). S 1 (M3)>S 1 (M1) …(Formula 2)

[0502] The energy gap T of the third compound at 77 [K] 77K (M3) is preferably larger than the energy gap T of the first compound at 77 [K] 77K (M1).

[0503] FIG. 6 is a diagram for explaining the principle of light emission according to the sixth embodiment of the present invention. In FIG. 6, 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(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. As shown in FIG. 6, when a compound with a small ΔST(M1) is used as the first compound, the lowest excited triplet state T1(M1) of the first compound can undergo reverse intersystem crossing to the lowest excited singlet state S1(M1) by thermal energy. By utilizing the reverse intersystem crossing occurring in this first compound, for example, light emission as shown in the following (i) or (ii) can be observed. (i) When the light-emitting layer does not contain a fluorescence dopant having a lowest excited singlet state S1 smaller than the lowest excited singlet state S1(M1) of the first compound, light emission from the lowest excited singlet state S1(M1) of the first compound can be observed. (ii) When the light-emitting layer contains a fluorescence dopant having a lowest excited singlet state S1 smaller than the lowest excited singlet state S1(M1) of the first compound (the fluorescent second compound in the fourth or fifth embodiment), light emission from the fluorescence dopant can be observed. In the organic EL element of the sixth embodiment, the light emission shown in the above (i) can be observed. In the organic EL element of the above-described fourth or fifth embodiment, the light emission shown in the above (ii) can be observed.

[0504] (Content ratio of the compound in the light-emitting layer) In the organic EL element according to the sixth embodiment, the content ratios of the first compound and the third compound contained in the light-emitting layer are preferably in the following ranges, for example. The content ratio of the first compound is preferably 10% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, still more preferably 10% by mass or more and 60% by mass or less, and still 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 90% by mass or less. The upper limit of the total content ratio of the first compound and the third compound in the light-emitting layer is 100% by mass. In the organic EL element according to the sixth embodiment, the light-emitting layer may contain only one kind of the first compound or two or more kinds thereof. The light-emitting layer may contain only one kind of the third compound or two or more kinds thereof.

[0505] Since the organic EL element according to the sixth embodiment contains the compound (first compound) according to the first embodiment, according to the sixth embodiment, the luminous efficiency of the organic EL element can be improved. Since the organic EL element according to the sixth embodiment contains the compound (first compound) according to the second embodiment, according to the sixth embodiment, the lifetime of the organic EL element can be improved. The organic EL element according to the sixth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0506] 〔Seventh Embodiment〕 (Electronic device) The electronic device according to the seventh embodiment incorporates 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.

[0507] 〔Modification of 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.

[0508] 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 of the light-emitting layers only needs to satisfy the conditions described in the above 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 due to electron transition from the triplet excited state directly to the ground state. Also, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0509] Further, 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 disposed in contact with the light-emitting layer and blocks at least any one of holes, electrons, and excitons. For example, when the barrier layer is disposed 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 (for example, 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 (for example, an electron transport layer and a hole transport layer, etc.). The light-emitting layer and the barrier layer are preferably joined.

[0510] In addition, specific structures, shapes, 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

[0511] Hereinafter, examples according to the present invention will be described. The present invention is not limited by these examples.

[0512] <Compound> The structures of the compounds represented by the general formula (1) or (1A) used in the production of the organic EL elements according to Examples 1 to 8 are shown below.

[0513]

Chemical formula

[0514]

Chemical formula

[0515]

Chemical formula

[0516] The structures of the compounds used in the production of the organic EL elements according to Comparative Examples 1 to 6 are shown below.

[0517] [Chemical formula]

[0518] The structures of other compounds used in the production of the organic EL elements according to Examples 1 to 8 and Comparative Examples 1 to 6 are shown below.

[0519] [Chemical formula]

[0520] [Chemical formula]

[0521] [Chemical formula]

[0522] [Chemical formula]

[0523] [Chemical formula]

[0524] [Fabrication of Organic EL Element] The organic EL element was fabricated and evaluated as follows.

[0525] (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 in thickness 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 glass substrate with the transparent electrode line after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, Compound HT1 and Compound HA were co-evaporated so as to cover the transparent electrode on the surface on which the transparent electrode line was formed, and a hole injection layer with a film thickness of 10 nm was formed. The concentration of Compound HT1 in the hole injection layer was 97% by mass, and the concentration of Compound HA was 3% by mass. Next, Compound HT1 was evaporated on this hole injection layer to form a first hole transport layer with a film thickness of 110 nm. Next, Compound HT2 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Next, Compound CBP was evaporated on this second hole transport layer to form an electron barrier layer with a film thickness of 5 nm. Next, Compound M3-1 as a third compound and Compound A1 as a first compound were co-evaporated on this electron barrier layer to form a light-emitting layer with a film thickness of 25 nm. The concentration of Compound M3-1 in the light-emitting layer was 50% by mass, and the concentration of Compound A1 was 50% by mass. Next, Compound HBL was evaporated on this light-emitting layer to form a hole barrier layer with a film thickness of 5 nm. Next, Compound ET1 was evaporated on this hole barrier layer to form an electron transport layer with a film thickness of 50 nm. Next, lithium fluoride (LiF) was evaporated on this electron transport layer to form an electron-injecting electrode (cathode) with a film thickness of 1 nm. Then, metal aluminum (Al) was evaporated on this electron-injecting electrode to form a metal Al cathode with a film thickness of 80 nm. The device structure of the organic EL device according to Example 1 is schematically shown as follows. ITO(130) / HT1:HA(10,97%:3%) / HT1(110) / HT2(5) / CBP(5) / M3-1:A1(25,50%:50%) / HBL(5) / ET1(50) / LiF(1) / Al(80) Note that the numbers in parentheses indicate the film thickness (unit: nm). Also, within the parentheses, the percentage numbers (97%:3%) indicate the ratios (by mass) of compound HT1 and compound HA in the hole injection layer, and the percentage numbers (50%:50%) indicate the ratios (by mass) of compound M3-1 and compound A1 in the light-emitting layer.

[0526] (Examples 2 to 3 and Comparative Examples 1 to 3) The organic EL elements according to Examples 2 to 3 and Comparative Examples 1 to 3 were each produced in the same manner as in Example 1, except that the first compound and the third compound in the light-emitting layer in Example 1 were changed to the first compound and the third compound described in Table 1.

[0527] (Example 4) 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 UV ozone cleaned for 1 minute. The film thickness of the ITO was 130 nm. The glass substrate with the transparent electrode line after cleaning was mounted on the substrate holder of a vacuum evaporation apparatus. First, compound HT1 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 HT1 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass. Next, compound HT1 was evaporated on this hole injection layer to form a first hole transport layer with a film thickness of 110 nm. Next, compound HT2 was evaporated on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm. Next, compound CBP was evaporated on this second hole transport layer to form an electron barrier layer with a film thickness of 5 nm. Next, compound M3-4 as the third compound, compound A1 as the first compound, and compound GD as the second compound were co-evaporated on this electron barrier layer to form a light-emitting layer with a film thickness of 25 nm. The concentration of compound M3-4 in the light-emitting layer was 59.2% by mass, the concentration of compound A1 was 40% by mass, and the concentration of compound GD was 0.8% by mass. Next, compound HBL was vapor-deposited on this light-emitting layer to form a hole barrier layer with a film thickness of 5 nm. Next, compound ET1 was vapor-deposited on this hole barrier layer to form an electron transport layer with a film thickness of 50 nm. Next, lithium fluoride (LiF) was vapor-deposited on this 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. When schematically showing the element structure of the organic EL element according to Example 4, it is as follows. ITO(130) / HT1:HA(10, 97%:3%) / HT1(110) / HT2(5) / CBP(5) / M3-4:A1:GD(25, 59.2%:40%:0.8%) / HBL(5) / ET1(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 HT1 and compound HA in the hole injection layer, and the percentage numbers (59.2%:40%:0.8%) indicate the ratio (mass%) of compound M3-4, compound A1, and compound GD in the light-emitting layer.

[0528] (Examples 5 to 7 and Comparative Examples 4 to 5) The organic EL elements according to Examples 5 to 7 and Comparative Examples 4 to 5 were each fabricated in the same manner as in Example 4, except that the first compound in the light-emitting layer in Example 4 was changed to the first compound described in Table 2.

[0529] (Examples 8 and Comparative Example 6) The organic EL elements according to Examples 8 and Comparative Example 6 were each fabricated in the same manner as in Example 4, except that the first compound in the light-emitting layer in Example 4 was changed to the first compound described in Table 3.

[0530] <Evaluation of Organic EL Element> For the fabricated organic EL elements, the evaluations described in Tables 1 to 3 were carried out. The evaluation results are shown in Tables 1 to 3. Note that the comparative compounds Ref-1 and Ref-2 used in Comparative Examples 1 to 6 do not correspond to the first compound, but are shown in the same column as the first compound for convenience. Also, the evaluation results of the compounds used in the light-emitting layers of each Example are shown in Tables 1 to 3.

[0531] (External quantum efficiency EQE) For the fabricated organic EL elements, when a voltage was applied so that the current density became 10.00 mA / cm 2 the spectral emission luminance spectrum was measured with a spectro-radiometer CS-2000 (manufactured by Konica Minolta, Inc.). Assuming that Lambertian emission was performed, the external quantum efficiency EQE (unit: %) was calculated from the obtained spectral emission luminance spectrum. Tables 1 and 2 show "External quantum efficiency EQE" (unit: %) and "EQE (relative value)" (unit: %). The "EQE (relative value)" shown in Table 1 was calculated based on the measured value of EQE for each example and the following mathematical formula (Equation 1X). The "EQE (relative value)" shown in Table 2 was calculated based on the measured value of EQE for each example and the following mathematical formula (Equation 2X) or (Equation 3X). EQE (relative value) = (EQE of Example X / EQE of Comparative Example X) × 100…(Equation 1X) (In Equation (Equation 1X), X is 1, 2, or 3.) EQE (relative value) = (EQE of Example Y / EQE of Comparative Example 4) × 100…(Equation 2X) (In Equation (Equation 2X), Y is 4, 5, 6, or 7.) EQE (relative value) = (EQE of Comparative Example 5 / EQE of Comparative Example 4) × 100…(Equation 3X)

[0532] (Lifetime LT95) For the fabricated organic EL elements, a voltage was applied so that the current density became 50 mA / cm 2 and the time (LT95 (unit: hr)) until the luminance became 95% of the initial luminance was measured as the lifetime. The luminance was measured using a spectro-radiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 3 shows "LT95" (unit: hr) and "LT95 (relative value)" (unit: %). "LT95 (relative value)" shown in Table 3 was calculated based on the following formula (Formula 4X). LT95 (relative value) = (LT95 of Example 8 / LT95 of Comparative Example 6) × 100…(Formula 4X)

[0533] (Maximum peak wavelength λp and emission half-width FWHM) When a voltage was applied to the organic EL element so that the current density became 10.00 mA / cm 2 the spectral emission luminance spectrum was measured with a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral emission luminance spectrum, the maximum peak wavelength λp (unit: nm) and the emission half-width FWHM (unit: nm) of the maximum peak wavelength λp were determined. FWHM is an abbreviation for Full Width at Half Maximum.

[0534] (CIE1931 chromaticity) When a voltage was applied to the organic EL element so that the current density became 10.00 mA / cm 2 the CIE1931 chromaticity coordinates (x, y) were measured with a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta).

[0535]

Table 1

[0536] In Example 1 where the compound A1 represented by the general formula (1) was used as the first compound, the luminous efficiency was improved as compared with Comparative Example 1 in which the compound A1 was replaced with the comparative compound Ref-1. Similarly, when Example 2 was compared with Comparative Example 2 and when Example 3 was compared with Comparative Example 3, the luminous efficiencies of Examples 2 and 3 were improved as compared with Comparative Examples 2 and 3, respectively.

[0537]

Table 2

[0538] In Examples 4 to 7 using the compounds A1 to A4 represented by the general formula (1) as the first compound, the luminous efficiency was improved as compared with Comparative Examples 4 and 5 in which the compounds A1 to A4 were replaced with Comparative Compounds Ref-1 or Ref-2, respectively.

[0539] [Table 3]

[0540] In Example 8 using the compound A5 represented by the general formula (1A) as the first compound, the lifetime was prolonged as compared with Comparative Example 6 in which the compound A5 was replaced with Comparative Compound Ref-1.

[0541] (Evaluation of Compounds) (Measurement of Fluorescence Quantum Yield (PLQY)) The compound to be measured was dissolved in toluene so that the concentration became 5 μmol / L to prepare a toluene solution. Then, the solution after preparation of the solution was nitrogen-bubbled for 5 minutes and sealed so that outside air did not mix in. For the prepared toluene solution of the compound to be measured, the PLQY was measured using an absolute PL (photoluminescence) quantum yield measuring device Quantaurus-QY (manufactured by Hamamatsu Photonics K.K.).

[0542] (Maximum Peak Wavelength of Compound) The maximum peak wavelength λ of the compound was measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and put into a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). In this example, the emission spectrum was measured with a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Technologies Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength λ.

[0543] (Delayed Fluorescence Property of Compound) The delayed fluorescence property was confirmed by measuring the transient PL using the apparatus shown in Fig. 1. Compound A1 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 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. After excitation with pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by Compound A1, 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 thereafter. The delayed fluorescence emission in this example means that the amount of Delay emission (delayed emission) is 5% or more relative 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 / X P it means that the value of is 0.05 or more. The amounts and ratio of Prompt emission and Delay emission 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 Reference 1 or the apparatus described in Fig. 1. Compounds A2 to A5 and comparative compounds Ref-1 and Ref-2 were also measured in the same manner as Compound A1. For compounds A1 to A5, comparative compounds Ref-1 and Ref-2, it was confirmed that the amount of delayed fluorescence was 5% or more of the amount of prompt fluorescence. Specifically, for compounds A1 to A5, comparative compounds Ref-1 and Ref-2, the value of X D / X P was 0.05 or more.

[0544] (Singlet energy S 1 ) The singlet energy S of the compound to be measured 1 was measured by the above solution method.

[0545] (Energy gap T 77K and ΔST) The energy gap T of the compound to be measured 77K was measured by the energy gap T measurement method described in the above "Relationship between triplet energy and energy gap at 77 [K]". 77K For compounds A1 to A5, comparative compounds Ref-1 and Ref-2, ΔST was confirmed from the value of the energy gap T 77K and the value of the above singlet energy S 1 . "<0.01" in the table indicates that ΔST is less than 0.01 eV.

[0546] [Synthesis of Compounds] [Synthesis of Compound A1]

[0547] [Chemical Formula]

[0548] Under a nitrogen atmosphere, 5.50 g (20.1 mmol) of 12H-[1]Benzothieno[2,3-a]carbazole, 0.804 g (20.1 mmol) of sodium hydride (containing 40% by mass of oil), and 50 mL of DMF were placed in a 200 mL three-necked flask and stirred at 0 °C for 15 minutes. Next, 1.50 g (9.14 mmol) of Intermediate a was added to the reaction mixture, and the mixture was stirred at room temperature for two and a half hours. The solid precipitated from the reaction mixture was collected by filtration and washed with ethyl acetate, methanol, and water to obtain 5.0 g of a yellow solid. It was identified as Intermediate c by ASAP-MS analysis (yield 82%). ASAP-MS is the abbreviation of Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[0549] Under a nitrogen atmosphere, 3.0 g (4.47 mmol) of Intermediate c, 0.927 g (6.71 mmol) of potassium carbonate, 0.050 g (0.224 mmol) of diacetoxypalladium, tricyclohexylphosphine (P(Cy) 3 )) (0.188 g, 0.671 mmol), 0.564 mL (5.37 mmol) of bromobenzene, 0.283 mL (1.79 mmol) of 2-ethylhexanoic acid, and 447 mL of chlorobenzene were placed in a 500 mL three-necked flask and stirred at 150 °C for 16 hours. Dichloromethane was added to the reaction solution, and it was passed through silica gel chromatography. After concentrating the obtained solution, it was purified again by silica gel chromatography to obtain 1.20 g of a yellow solid. It was identified as Compound A1 by GC-MS analysis (yield 36%).

[0550] <Synthesis of Compound A2>

[0551]

Chemical formula

[0552] Under a nitrogen atmosphere, into a 500 mL three-necked flask were added intermediate c (3.0 g, 4.47 mmol), potassium carbonate (0.927 g, 6.71 mmol), diacetoxypalladium (0.050 g, 0.224 mmol), tricyclohexylphosphine (0.188 g, 0.671 mmol), 4-bromobiphenyl (1.49 mL, 8.94 mmol), 2-ethylhexanoic acid (0.283 mL, 1.79 mmol) and Chlorobenzene (300 mL). The mixture was stirred at 150 °C for 14 hours. The precipitated solid was collected by filtration and washed with water and dichloromethane. The obtained solid was purified by silica gel chromatography to obtain 1.70 g of a yellow solid. It was identified as compound A2 by GC-MS analysis (yield 46%).

[0553] <Synthesis of Compound A3>

[0554]

Chemical formula

[0555] Under a nitrogen atmosphere, into a 500 mL three-necked flask were added intermediate c (3.0 g, 4.47 mmol), potassium carbonate (0.927 g, 6.71 mmol), diacetoxypalladium (0.050 g, 0.224 mmol), tricyclohexylphosphine (0.188 g, 0.671 mmol), 3-bromobiphenyl (1.49 mL, 8.94 mmol), 2-ethylhexanoic acid (0.283 mL, 1.79 mmol) and Chlorobenzene (300 mL). The mixture was stirred at 150 °C for 14 hours. The precipitated solid was collected by filtration and washed with water and dichloromethane. The obtained solid was purified by silica gel chromatography to obtain 1.70 g of a yellow solid. It was identified as compound A3 by GC-MS analysis (yield 35%).

[0556] <Synthesis of Compound A4>

[0557]

Chemical formula

[0558] Under a nitrogen atmosphere, into a 500 mL three-necked flask were added intermediate c (3.0 g, 4.47 mmol), potassium carbonate (0.927 g, 6.71 mmol), diacetoxypalladium (0.050 g, 0.224 mmol), tricyclohexylphosphine (0.188 g, 0.671 mmol), 1-bromo-3,5-diphenylbenzene (2.77 g, 8.94 mmol), 2-ethylhexanoic acid (0.283 mL, 1.79 mmol), and chlorobenzene (300 mL). The mixture was stirred at 150 °C for 14 hours. The precipitated solid was collected by filtration and washed with water and dichloromethane. The obtained solid was purified by silica gel chromatography to obtain 0.80 g of a yellow solid. It was identified as compound A4 by GC-MS analysis (yield 20%).

[0559] <Synthesis of Compound A5>

[0560]

Chemical Structure

[0561] Under a nitrogen atmosphere, into a 100 mL three-necked flask were added intermediate a (2.5 g, 15.2 mmol), potassium carbonate (3.0 g, 21.7 mmol), diacetoxypalladium (0.171 g, 0.762 mmol), tricyclohexylphosphine (0.641 g, 2.29 mmol), 1-bromo-3,5-diphenylbenzene (5.65 g, 18.3 mmol), 2-ethylhexanoic acid (0.241 mL, 1.52 mmol), and xylene (50 mL). The mixture was stirred at 80 °C for 7 hours. 500 mL of dichloromethane was added to the reaction solution and stirred, and the precipitated solid was removed. The obtained filtrate was concentrated under reduced pressure. The obtained solid was purified by silica gel chromatography to obtain 1.9 g of a white solid. It was identified as intermediate d by GC-MS and NMR analyses (yield 32%).

[0562] Under a nitrogen atmosphere, 4-phenyl-12H-[1]Benzothieno[2,3-a]carbazole (1.76 g, 5.05 mmol), sodium hydride (containing 40% by mass oil) (0.193 g, 4.82 mmol), and 20 mL of DMF were placed in a 100 mL three-necked flask and stirred at 0 °C for 15 minutes. Next, intermediate d (0.90 g, 2.29 mmol) was added to the reaction mixture and stirred at room temperature for one and a half hours. The solid precipitated from the reaction mixture was collected by filtration and washed with methanol. The obtained solid was generated by column chromatography to obtain 1.6 g of a yellow solid. It was identified as compound A5 by ASAP-MS analysis (yield 31%).

[0563] <Synthesis of Comparative Compound Ref-1>

[0564]

Chemical formula

[0565] Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (165 g, 607 mmol), copper cyanide (120 g, 1335 mmol), and 800 mL of NMP were placed in a 2 L three-necked flask and stirred at 150 °C for 5 hours. 1 L of methylene chloride was added to the reaction mixture, filtered using celite, and the filtrate was concentrated using an evaporator. The obtained solid was purified by silica gel chromatography to obtain 58 g of a white solid. It was identified as intermediate a by GC-MS analysis (yield 58%).

[0566] Under a nitrogen atmosphere, into a 500 mL three-necked flask, intermediate a (20 g, 122 mmol), potassium carbonate (25.3 g, 183 mmol), diacetoxypalladium (0.410 g, 1.83 mmol), Xphos (1.74 g, 3.66 mmol), bromobenzene (10.8 mL, 104 mmol), 2-ethylhexanoic acid (1.95 mL, 12.2 mmol) and Toluene (300 mL) were added, and the mixture was stirred at 40 °C for 16 hours. 500 mL of water was added to the reaction solution and stirred, and the precipitated solid was collected by filtration. The obtained solid was washed with 100 mL of water and 200 mL of methanol, and dried. The obtained solid was purified by silica gel chromatography and recrystallization from Toluene to obtain 13.2 g of a white solid. It was identified as intermediate b by GC-MS and NMR analysis (yield 45%).

[0567] Under a nitrogen atmosphere, into a 100 mL three-necked flask, 12H-[1]Benzothieno[2,3-a]carbazole (2.00 g, 7.33 mmol), sodium hydride (containing 40% by mass oil) (0.280 g, 6.99 mmol), and 11 mL of DMF were added, and the mixture was stirred at 0 °C for 20 minutes. Next, intermediate b (0.80 g, 3.33 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 45 minutes. The solid precipitated from the reaction mixture was collected by filtration, washed with methanol, and purified by silica gel column chromatography to obtain 1.4 g of a yellow solid. It was identified as compound Ref-1 by ASAP-MS analysis (yield 56%).

[0568] <Synthesis of Comparative Compound Ref-2>

[0569]

Chemical Structure

[0570] Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (50 g, 184 mmol), chlorotrimethylsilane (60 g, 552 mmol), and THF (200 mL) were placed in a 1000 mL three-necked flask. The materials in the three-necked flask were cooled to -78 °C in a dry ice / acetone bath, and then 230 mL (2 M, THF solution) of lithium diisopropylamide was added dropwise. The mixture was stirred at -78 °C for 2 hours, then returned to room temperature and stirred for an additional 2 hours. After stirring, water (200 mL) was added to the three-necked flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. The resulting intermediate a2 (73 g, 175 mmol, yield 95%) was used in the next reaction without purification. Chlorotrimethylsilane may be abbreviated as TMSCl. In the chemical formula of intermediate a2, TMS is a trimethylsilyl group. LDA is an abbreviation for lithium diisopropylamide.

[0571] Under a nitrogen atmosphere, intermediate a2 (73 g, 175 mmol) and dichloromethane (200 mL) were placed in a 1000 mL eggplant flask. Iodine monochloride (85 g, 525 mmol) was dissolved in dichloromethane (200 mL), added dropwise at 0 °C, and then the mixture was stirred at 40 °C for 4 hours. After stirring, the mixture was returned to room temperature, a saturated aqueous sodium bisulfite solution (100 mL) was added, the organic layer was extracted with dichloromethane, the extracted organic layer was washed with water and brine, the washed organic layer was dried over magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate b2 (65 g, 124 mmol, yield 71%).

[0572] Under a nitrogen atmosphere, into a 500 mL three-necked flask were added intermediate b2 (22 g, 42 mmol), phenylboronic acid (12.8 g, 105 mmol), palladium acetate (0.47 g, 2.1 mmol), sodium carbonate (22 g, 210 mmol), and methanol (150 mL), and the mixture was stirred at 80 °C for 4 hours. After stirring, the reaction solution was allowed to cool to room temperature, and then the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and the washed organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate c2 (10 g, 24 mmol, yield 56%). The structure of the compound after purification was identified by ASAP-MS.

[0573] Under a nitrogen atmosphere, into a 200 mL three-necked flask were added intermediate c2 (10 g, 24 mmol), copper cyanide (10.6 g, 118 mmol), and DMF (15 mL), and the mixture was heated and stirred at 150 °C for 8 hours. After stirring, the mixture was cooled to room temperature, and then the reaction solution was poured into 10 mL of aqueous ammonia. Next, the organic layer was extracted with methylene chloride, the extracted organic layer was washed with water and brine, and the washed organic layer was dried over magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator, and the compound obtained after removal under reduced pressure was purified by silica gel column chromatography to obtain intermediate d2 (5.8 g, 18.34 mmol, yield 78%). DMF is the abbreviation of N,N-dimethylformamide.

[0574] Under a nitrogen atmosphere, into a 100 mL three-necked flask were added intermediate d2 (1.0 g, 3.2 mmol), 12H-[1]Benzothieno[2,3-a]carbazole (1.9 g, 7 mmol), potassium carbonate (1.3 g, 9.50 mmol), and 30 mL of DMF, and the mixture was stirred at 120 °C for 6 hours. After stirring, the precipitated solid was collected by filtration and purified by silica gel column chromatography to obtain compound Ref-2 (1.8 g, 2.2 mmol, yield 69%). The obtained compound was identified as compound Ref-2 by ASAP-MS analysis.

Explanation of Symbols

[0575] 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 (1). 【Chemical 1】 (In the general formula (1), D １ and D ２ each independently represents a group represented by the following general formula (11), general formula (12) or general formula (13): However, D １ and D ２ at least one of which is a group represented by the following general formula (12) or general formula (13): Rx is a halogen 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 5 to 6 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, a group represented by the following formula (12), or a group represented by the following formula (13), provided that Rx is not a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, and a substituted or unsubstituted triazinyl group.) 【Chemical 2】 [Chemical Formula 3] [Chemical Formula 4] (In the general formulas (11) to (13), R １ to R ８ Among them, one or more sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R １１ ~R １８ Among them, one or more sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R １１１ to R １１８ Among them, one or more sets consisting of two or more adjacent ones are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R that does not form the monocyclic ring and does not form the condensed ring １ ~R ８ 、R １１ ~R １８ and R １１１ ~R １１８ are each independently a hydrogen atom, a halogen 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, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms in the ring structure, In the general formula (12) and the general formula (13), A, B, and C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (14), (15), (15A), and (15B); The ring structure A, the ring structure B, and the ring structure C are condensed with an adjacent ring structure at an arbitrary position, p, px, and py are each independently 1, 2, 3, or 4, When p is 2, 3, or 4, the plurality of ring structures A are the same as or different from each other, When px is 2, 3, or 4, the plurality of ring structures B are the same as or different from each other, When py is 2, 3, or 4, the plurality of ring structures C are the same as or different from each other, However, D １ and D ２ at least one of which is p is 2, 3, or 4, and the group represented by the general formula (12) includes a ring structure represented by the following general formula (15A) or (15B) as the ring structure A, or At least one of px and py is 2, 3, or 4, and the group represented by the general formula (13) includes a ring structure represented by the following general formula (15A) or (15B) as the ring structure B or the ring structure C, * in the general formulas (11) to (13) indicates the bonding position with the benzene ring in the general formula (1).) 【Chemical Formula 5】 (In the general formulas (14) and (15), R １９ and R ２０ in the set of, Combined with each other to form a substituted or unsubstituted monocyclic ring, Combined with each other to form a substituted or unsubstituted condensed ring, or Do not combine with each other, R １２０ and R that do not form the monocyclic ring and do not form the condensed ring １９ and R ２０ are each independently R in the general formula (11) １ to R ８ and have the same meaning as.)

2. In the general formula (12), R １１ ~R １８ Among them, any combination consisting of two or more adjacent ones does not bond to each other. In the general formula (13), R １１１ ~R １１８ Among them, any combination consisting of two or more adjacent ones does not bond to each other. The compound according to claim 1.

3. Having at least one group represented by the general formula (12), The compound according to claim 1 or claim 2.

4. The group represented by the general formula (12) is any group selected from the group consisting of groups represented by the following general formulas (12A), (12B), (12C), (12D), (12E), and (12F), The compound according to any one of claims 1 to 3. 【Chemical Formula 6】 [Chemical Formula 7] [Chemical 8] 【Chemical Formula 9】 【Chemical 10】 【Chemical Formula 11】 (In the general formulas (12A), (12B), (12C), (12D), (12E), and (12F), X １ is NR １２０ , a sulfur atom, or an oxygen atom, and R １１ ~R １８ each independently has the same meaning as R in the general formula (12). １１ ~R １８ and is synonymous with R １９ and R ２０ each independently represents R in the general formula (14), １９ and R ２０ and has the same meaning as R １２０ is synonymous with R in the general formula (15), １２０ and * in the general formulas (12A), (12B), (12C), (12D), (12E), and (12F) indicates the bonding position with the benzene ring in the general formula (1).)

5. The group represented by the general formula (12) is any group selected from the group consisting of groups represented by the general formulas (12A), (12D), and (12F), The compound according to claim 4.

6. X １ is an oxygen atom or a sulfur atom, The compound according to any one of Claims 1 to 5.

7. R １ ~R ８ , R １１ ~R ２０ , R １１１ ~R １１８ and R １２０ are each 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, The compound according to any one of Claims 1 to 6.

8. R １ ~R ８ , R １１ ~R ２０ , R １１１ ~R １１８ and R １２０ are each independently A hydrogen atom, A substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or A substituted or unsubstituted cycloalkyl group having 3 to 6 ring-forming carbon atoms, The compound according to any one of Claims 1 to 7.

9. Rx is A halogen atom, An unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, An unsubstituted alkyl group having 5 to 6 carbon atoms, An unsubstituted alkylsilyl group having 3 to 6 carbon atoms, An unsubstituted arylsilyl group having 3 to 6 carbon atoms, An unsubstituted alkoxy group having 1 to 6 carbon atoms, An unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, An unsubstituted alkylamino group having 2 to 12 carbon atoms, An unsubstituted alkylthio group having 1 to 6 carbon atoms, An unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, An unsubstituted quinolyl group, An unsubstituted isoquinolyl group, An unsubstituted quinazolinyl group, An unsubstituted benzimidazolyl group, An unsubstituted phenanthrolinyl group, A substituted or unsubstituted benzocarbazolyl group, A substituted or unsubstituted azacarbazolyl group, A substituted or unsubstituted diazacarbazolyl group, An unsubstituted dibenzofuranyl group, An unsubstituted naphthobenzofuranyl group, An unsubstituted azadibenzofuranyl group, An unsubstituted diazadibenzofuranyl group, An unsubstituted dibenzothiophenyl group, An unsubstituted naphthobenzothiophenyl group, An unsubstituted azadibenzothiophenyl group, or An unsubstituted diazadibenzothiophenyl group, The compound according to any one of Claims 1 to 8.

10. Rx is An unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, An unsubstituted alkyl group having 5 to 6 carbon atoms, An unsubstituted quinolyl group, An unsubstituted isoquinolyl group, An unsubstituted quinazolinyl group, An unsubstituted benzimidazolyl group, An unsubstituted phenanthrolinyl group, A substituted or unsubstituted benzocarbazolyl group, A substituted or unsubstituted azacarbazolyl group, A substituted or unsubstituted diazacarbazolyl group, An unsubstituted dibenzofuranyl group, An unsubstituted naphthobenzofuranyl group, An unsubstituted azadibenzofuranyl group, An unsubstituted diazadibenzofuranyl group, An unsubstituted dibenzothiophenyl group, An unsubstituted naphthobenzothiophenyl group, An unsubstituted azadibenzothiophenyl group, or An unsubstituted diazadibenzothiophenyl group, The compound according to any one of claims 1 to 9.

11. A compound represented by the following general formula (1A). 【Chemical 12】 (In the general formula (1A), D ３ and D ４ each independently represents a group represented by the following general formula (11), general formula (12), or general formula (13). However, D ３ and D ４ at least one of which is a group represented by the following general formula (12) or general formula (13): Ry is A halogen atom, A substituted or unsubstituted aryl group having 13 to 30 ring-forming carbon atoms, A substituted or unsubstituted heteroaryl group having 6 to 30 ring-forming atoms, A substituted or unsubstituted alkyl group having 5 to 6 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, A substituted or unsubstituted arylsilyl group having 3 to 6 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 14 ring-forming carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 12 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or A substituted or unsubstituted arylthio group having 6 to 14 ring-forming carbon atoms, A group represented by the following formula (12), or A group represented by the following formula (13).) 【Chemical 13】 【Chemical 14】 【Chemical Formula 15】 (In the general formulas (11) to (13), R １ ~R ８ Among them, one or more sets consisting of two or more adjacent ones are They are bonded to each other to form a substituted or unsubstituted monocyclic ring, They are bonded to each other to form a substituted or unsubstituted condensed ring, or They are not bonded to each other, R １１ to R １８ among which, at least one set consisting of two or more adjacent ones They are bonded to each other to form a substituted or unsubstituted monocyclic ring, They are bonded to each other to form a substituted or unsubstituted condensed ring, or They are not bonded to each other, R １１１ to R １１８ Among them, at least one set consisting of two or more adjacent ones They are bonded to each other to form a substituted or unsubstituted monocyclic ring, They are bonded to each other to form a substituted or unsubstituted condensed ring, or They are not bonded to each other, R that does not form the single ring and does not form the condensed ring １ ~R ８ 、R １１ ~R １８ and R １１１ ~R １１８ are each independently A hydrogen atom, A halogen 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, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 60 ring-forming carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring-forming carbon atoms, A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 60 ring-forming carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring-forming carbon atoms, and However, R １ to R ８ , R １１ to R １８ and R １１１ to R １１８ is not an unsubstituted biphenyl group and is not a substituted or unsubstituted dibenzofuranyl group, in the general formula (12) and the general formula (13), A, B and C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (14), (15), (15A) and (15B); the ring structure A, the ring structure B and the ring structure C are condensed with an adjacent ring structure at an arbitrary position, p, px and py are each independently 1, 2, 3 or 4, when p is 2, 3 or 4, a plurality of ring structures A are the same as or different from each other, when px is 2, 3 or 4, a plurality of ring structures B are the same as or different from each other, when py is 2, 3 or 4, a plurality of ring structures C are the same as or different from each other, * in the general formulas (11) to (13) indicates the bonding position to the benzene ring in the general formula (1A).) 【Chemical 16】 (In the general formulas (14) and (15), R １９ and R ２０ of the pair are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R １２０ and R that do not form the monocyclic ring and do not form the condensed ring １９ and R ２０ are each independently R in the general formula (11) １ to R ８ and have the same meaning as.)

12. In the general formula (12), R １１ ~R １８ Among them, any group consisting of two or more adjacent ones does not bond to each other, In the general formula (13), R １１１ ~R １１８ Among them, any combination consisting of two or more adjacent ones does not bond to each other. The compound according to claim 11.

13. The compound according to claim 11 or claim 12, having at least one group represented by the general formula (12).

14. The group represented by the general formula (12) is any group selected from the group consisting of groups represented by the following general formulas (12A), (12B), (12C), (12D), (12E) and (12F), The compound according to any one of claims 11 to 13. (In the general formulas (12A), (12B), (12C), (12D), (12E) and (12F), 【Chemical 17】 【Chemical 18】 【Chemical Formula 19】 【Chemical 20】 【Chemical 21】 【Chemical 22】 * in the general formulas (12A), (12B), (12C), (12D), (12E) and (12F) indicates the bonding position to the benzene ring in the general formula (1A).) X １ is NR １２０ , a sulfur atom, or an oxygen atom, and R １１ to R １８ each independently represents R in the general formula (12) １１ to R １８ and has the same meaning as R １９ and R ２０ each independently is synonymous with R in the general formula (14) １９ and R ２０ and is R １２０ is synonymous with R in the general formula (15), １２０ and

15. The group represented by the general formula (12) is any group selected from the group consisting of groups represented by the general formulas (12A), (12D) and (12F), The compound according to claim 14.

16. The compound according to any one of claims 11 to 15. X １ is an oxygen atom or a sulfur atom,

17. A hydrogen atom, R １ ~R ８ , R １１ ~R ２０ , R １１１ ~R １１８ and R １２０ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, ​ A cycloalkyl group having 3 to 30 carbon atoms in the ring, which may or may not be substituted, A phenyl group which may or may not be substituted, A naphthyl group which may or may not be substituted, An imidazolyl group which may or may not be substituted, A pyrazolyl group which may or may not be substituted, A triazolyl group which may or may not be substituted, A tetrazolyl group which may or may not be substituted, An oxazolyl group which may or may not be substituted, An isoxazolyl group which may or may not be substituted, An oxadiazolyl group which may or may not be substituted, A thiazolyl group which may or may not be substituted, An isothiazolyl group which may or may not be substituted, A thiadiazolyl group which may or may not be substituted, A pyridyl group which may or may not be substituted, A pyridazinyl group which may or may not be substituted, A pyrimidinyl group which may or may not be substituted, A pyrazinyl group which may or may not be substituted, A triazinyl group which may or may not be substituted, An indolyl group which may or may not be substituted, An isoindolyl group which may or may not be substituted, An indolizinyl group which may or may not be substituted, A quinolizinyl group which may or may not be substituted, A quinolyl group which may or may not be substituted, An isoquinolyl group which may or may not be substituted, A cinnolyl group which may or may not be substituted, A phthalazinyl group which may or may not be substituted, A quinazolinyl group which may or may not be substituted, A quinoxalinyl group which may or may not be substituted, A benzimidazolyl group which may or may not be substituted, An indazolyl group which may or may not be substituted, A morpholino group which may or may not be substituted, A furyl group which may or may not be substituted, An oxazolyl group which may or may not be substituted, An isoxazolyl group which may or may not be substituted, An oxadiazolyl group which may or may not be substituted, A morpholino group which may or may not be substituted, A thienyl group which may or may not be substituted, A thiazolyl group which may or may not be substituted, An isothiazolyl group which may or may not be substituted, or A thiadiazolyl group which may or may not be substituted, The compound according to any one of claims 11 to 16.

18. Ry is A halogen atom, An aryl group having 13 to 30 carbon atoms in the ring, which may or may not be substituted, A heteroaryl group having 6 to 30 ring-forming atoms, which may or may not be substituted, or An alkyl group having 5 to 6 carbon atoms, which may or may not be substituted. The compound according to any one of claims 11 to 17.

19. Containing the compound according to any one of claims 1 to 18, A material for an organic electroluminescence device.

20. Having an anode, a cathode, and an organic layer, The organic layer contains the compound according to any one of claims 1 to 18 as a first compound. An organic electroluminescence device.

21. In the organic electroluminescence device according to claim 20, the organic layer has at least one light-emitting layer, and the light-emitting layer contains the first compound. An organic electroluminescence device.

22. The light-emitting layer contains the first compound and further a second compound, and the second compound is a fluorescent compound. The singlet energy S of the first compound １ (M1) and the singlet energy S of the second compound １ (M2) satisfy the relationship of the following mathematical formula (Formula 1): An organic electroluminescence device according to claim 21. S １ (M1) > S １ (M2) … (Number 1)

23. The light-emitting layer contains the first compound and further a third compound. The singlet energy S of the first compound １ (M1) and the singlet energy S of the third compound １ (M3) satisfy the relationship of the following mathematical formula (Formula 2): An organic electroluminescence device according to claim 21. S １ (M3) > S １ (M1) … (Equation 2)

24. The light-emitting layer contains the first compound, further a second compound, and a third compound, and the second compound is a fluorescent compound. The singlet energy S of the first compound １ (M1), and the singlet energy S of the second compound １ (M2), and the singlet energy S of the third compound １ (M3) satisfy the relationship of the following mathematical formula (Formula 3): An organic electroluminescence device according to claim 21. S １ (M3) > S １ (M1) > S １ (M2) … (Equation 3)

25. An electronic device equipped with the organic electroluminescence device according to any one of claims 20 to 24.

Images