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

Abstract

A compound represented by formula (1). # imgabs0 #

Description

Technical Field

[0001] The present invention relates to novel compounds, materials for organic electroluminescent elements, organic electroluminescent elements and electronic equipment. Background Art

[0002] When voltage is applied to an organic electroluminescent element (hereinafter also referred to as an organic EL element), holes are injected from the anode 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.

[0003] The device performance of conventional organic EL devices is still insufficient. In order to improve the device performance, the materials used in the organic EL devices have been gradually improved, but further performance improvement is still required. Summary of the invention

[0004] An object of the present invention is to provide a high-performance organic EL element and a compound capable of realizing the organic EL element.

[0005] The present inventors have conducted intensive studies to achieve the above-mentioned object and have found that a compound having a specific structure contributes to the improvement of the performance of an organic EL element, thereby completing the present invention.

[0006] According to the present invention, the following compounds and the like are provided.

[0007] 1. A compound represented by the following formula (1),

[0008] [Chemistry 1]

[0009]

[0010] In formula (1),

[0011] X 1 and X 2 are each independently N or CH, X 1 and X 2 Any one of is N;

[0012] Ar 1 and Ar 2 Each independently is:

[0013] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0014] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0015] L 1 ~L 3 Each independently is:

[0016] single bond,

[0017] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0018] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

[0019] n1 is an integer from 0 to 4. When n1 is 0, (L 1 ) n1 is a single bond; L 1 When there are multiple L 1 Each can be the same or different;

[0020] n2 is an integer from 0 to 4. When n2 is 0, (L 2 ) n2 is a single bond; L 2 When there are multiple L 2 Each can be the same or different;

[0021] n3 is an integer of 0 to 4. When n3 is 0, (L 3 ) n3 is a single bond; L 3 When there are multiple L 3 Each can be the same or different;

[0022] R 11 ~R 19 Each independently is a hydrogen atom or a substituent R; 11 ~R 19 The adjacent groups of two or more are not bonded to each other;

[0023] R 21 and R 22 Bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring;

[0024] The aforementioned R which does not form a substituted or unsubstituted saturated or unsaturated ring 21 and R 22 Each independently is:

[0025] Hydrogen atoms,

[0026] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0027] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

[0028] The substituent R is selected from:

[0029] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0030] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0031] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0032] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0033] -Si(R 901 )(R 902 )(R 903 ),

[0034] -O-(R 904 ),

[0035] -S-(R 905 ),

[0036] -N(R 906 )(R 907 ),

[0037] Halogen atoms, cyano, nitro,

[0038] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0039] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0040] R 901 ~R 907 Each independently is:

[0041] Hydrogen atoms,

[0042] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0043] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0044] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0045] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0046] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 Each can be the same or different;

[0047] When there are two or more substituents R, the two or more substituents R may be the same or different.

[0048] 2. An organic electroluminescent element having:

[0049] cathode,

[0050] Anode, and

[0051] One or more organic layers disposed between the cathode and the anode;

[0052] At least one of the organic layers contains the compound described in 1 above.

[0053] 3. An electronic device comprising the organic electroluminescent element described in 2 above.

[0054] According to the present invention, a high-performance organic EL element and a compound capable of realizing the organic EL element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0055] Figure 1 : is a diagram showing a schematic structure of an organic EL element involved in one embodiment of the present invention. DETAILED DESCRIPTION

[0056] [definition]

[0057] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0058] In the present specification, in chemical structural formulas, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded to a position capable of bonding that is not explicitly indicated by symbols such as "R" or "D" representing a deuterium atom.

[0059] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are combined to form a ring structure. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" recorded below is the same unless otherwise specified. For example, the number of ring carbon atoms of the benzene ring is 6, the number of ring carbon atoms of the naphthalene ring is 10, the number of ring carbon atoms of the pyridine ring is 5, and the number of ring carbon atoms of the furan ring is 4. In addition, for example, the number of ring carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring carbon atoms of 9,9'-spirobifluorenyl is 25.

[0060] In addition, when the benzene ring is substituted with an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms in the ring of the benzene ring. Therefore, the number of carbon atoms in the ring of the benzene ring substituted with an alkyl group is 6. In addition, when the naphthalene ring is substituted with an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms in the ring of the naphthalene ring. Therefore, the number of carbon atoms in the ring of the naphthalene ring substituted with an alkyl group is 10.

[0061] In this specification, the number of ring atoms represents the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) whose atoms are combined into a cyclic structure (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is also the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, for example, hydrogen atoms bonded to carbon atoms of the quinoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinoline ring. Therefore, the number of ring atoms of the quinoline ring to which hydrogen atoms or substituents are bonded is 10.

[0062] In the present specification, "the number of carbon atoms XX to YY" in the expression "ZZ group having XX to YY carbon atoms which may be substituted or unsubstituted" means the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the group is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0063] In the present specification, "the number of atoms XX to YY" in the expression "ZZ group having XX to YY atoms, which may be substituted or unsubstituted" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when the group is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0064] In the present specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0065] In the present specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0066] In addition, in the present specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by AA group.

[0067] "Substituents described in this specification"

[0068] Hereinafter, the substituents described in the present specification will be described.

[0069] Unless otherwise specified in the present specification, the “unsubstituted aryl group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0070] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0071] Unless otherwise specified in the present specification, the “unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0072] Unless otherwise specified in the present specification, the “unsubstituted alkenyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0073] Unless otherwise specified in the present specification, the “unsubstituted alkynyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0074] Unless otherwise specified in the present specification, the “unsubstituted cycloalkyl group” described in the present specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6.

[0075] Unless otherwise specified in the present specification, the “unsubstituted arylene group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0076] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0077] Unless otherwise specified in the present specification, the “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0078] "Substituted or unsubstituted aryl"

[0079] As specific examples of "substituted or unsubstituted aryl groups" described in this specification (specific example group G1), the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B) can be cited. (Here, unsubstituted aryl groups refer to the case where "substituted or unsubstituted aryl groups" are "unsubstituted aryl groups", and substituted aryl groups refer to the case where "substituted or unsubstituted aryl groups" are "substituted aryl groups".) In this specification, when "aryl groups" are mentioned alone, both "unsubstituted aryl groups" and "substituted aryl groups" are included.

[0080] "Substituted aryl" means that one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent. Examples of "substituted aryl" include, for example, groups in which one or more hydrogen atoms of an "unsubstituted aryl" of the following specific example group G1A are replaced by a substituent, and examples of substituted aryl groups of the following specific example group G1B can be cited. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atoms bonded to the carbon atoms of the aryl itself in the "substituted aryl" of the following specific example group G1B are further replaced by a substituent, and groups in which the hydrogen atoms of the substituents in the "substituted aryl" of the following specific example group G1B are further replaced by substituents.

[0081] Unsubstituted aryl (specific example group G1A):

[0082] Phenyl,

[0083] p-Biphenyl,

[0084] m-Biphenyl,

[0085] o-Biphenyl,

[0086] 4-terphenyl-4-yl,

[0087] 4-terphenyl-3-yl,

[0088] 4-terphenyl-2-yl,

[0089] 4-terphenyl,

[0090] 3-terphenyl-1,

[0091] m-terphenyl-2-yl,

[0092] o-terphenyl-4-yl,

[0093] o-terphenyl-3-yl,

[0094] o-terphenyl-2-yl,

[0095] 1-naphthyl,

[0096] 2-naphthyl,

[0097] Anthracene,

[0098] Benzanthryl,

[0099] Fiki,

[0100] Triphenylene,

[0101] Phenyl,

[0102] Pyrene

[0103] base,

[0104] Benzo base,

[0105] Triphenylene,

[0106] Benzotriphenylene,

[0107] Tetraphenylene,

[0108] Pentaphenyl,

[0109] Fluorene,

[0110] 9,9'-Spirobifluorenyl,

[0111] Benzofluorenyl,

[0112] Dibenzofluorenyl,

[0113] Fluoranthene group,

[0114] Benzofluoranthene,

[0115] Perylene, and

[0116] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0117] [Chemistry 2]

[0118]

[0119] [Chemistry 3]

[0120]

[0121] Substituted aryl (specific example group G1B):

[0122] o-Toluyl,

[0123] m-Toluene

[0124] p-Tolyl,

[0125] p-Xylyl,

[0126] m-Xylyl,

[0127] o-Xylyl,

[0128] p-Isopropylphenyl,

[0129] m-isopropylphenyl,

[0130] o-isopropylphenyl,

[0131] 4-tert-Butylphenyl,

[0132] m-tert-butylphenyl,

[0133] o-tert-butylphenyl,

[0134] 3,4,5-Trimethylphenyl,

[0135] 9,9-dimethylfluorenyl,

[0136] 9,9-Diphenylfluorenyl

[0137] 9,9-bis(4-methylphenyl)fluorenyl,

[0138] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0139] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0140] Cyanophenyl,

[0141] Triphenylsilylphenyl,

[0142] Trimethylsilylphenyl,

[0143] Phenyl naphthyl,

[0144] naphthylphenyl, and

[0145] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above-mentioned general formulae (TEMP-1) to (TEMP-15) are replaced by a substituent.

[0146] "Substituted or unsubstituted heterocyclic group"

[0147] The "heterocyclic group" described in the present specification is a cyclic group containing at least one heteroatom among 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.

[0148] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0149] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0150] As specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (specific example group G2), the following unsubstituted heterocyclic group (specific example group G2A), and substituted heterocyclic group (specific example group G2B) can be cited. (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 a "heterocyclic group" is mentioned alone, both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" are included.

[0151] “Substituted heterocyclic group” means a group in which one or more hydrogen atoms of an “unsubstituted heterocyclic group” are replaced by a substituent. Specific examples of “substituted heterocyclic group” include groups in which hydrogen atoms of the “unsubstituted heterocyclic group” of the following specific example group G2A are replaced, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of “unsubstituted heterocyclic group” and “substituted heterocyclic group” listed here are only examples, and the “substituted heterocyclic group” described in this specification includes groups in which hydrogen atoms bonded to ring 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 hydrogen atoms of substituents in the “substituted heterocyclic group” of the specific example group G2B are further replaced by substituents.

[0152] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0153] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing nitrogen atoms (specific example group G2B1), substituted heterocyclic groups containing oxygen atoms (specific example group G2B2), substituted heterocyclic groups containing sulfur atoms (specific example group G2B3), and groups formed by replacing one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) with a substituent (specific example group G2B4).

[0154] ·Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0155] Pyrrolyl,

[0156] Imidazole,

[0157] Pyrazolyl,

[0158] Triazole,

[0159] Tetrazolyl,

[0160] Oxazolyl,

[0161] Isoxazolyl,

[0162] Oxadiazolyl,

[0163] Thiazolyl,

[0164] Isothiazolyl,

[0165] Thiadiazole,

[0166] Pyridyl,

[0167] Pyridazine

[0168] Pyrimidine,

[0169] Pyrazinyl,

[0170] Triazine,

[0171] Indolyl,

[0172] Isoindolyl,

[0173] Indolizinyl,

[0174] Quinolizinyl,

[0175] Quinoline,

[0176] Isoquinolinyl,

[0177] Cinnoline,

[0178] Phthalocyanine

[0179] Quinazoline,

[0180] Quinoxaline,

[0181] Benzimidazolyl,

[0182] Indazolyl,

[0183] Phenanthroline,

[0184] Phenanthridinyl,

[0185] Acridinium,

[0186] Phenolic acid,

[0187] Carbazolyl,

[0188] Benzocarbazolyl,

[0189] Morpholino,

[0190] Phenoxazine,

[0191] Phenothiazine,

[0192] azacarbazolyl, and diazacarbazolyl.

[0193] · Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0194] Furanyl,

[0195] Oxazolyl,

[0196] Isoxazolyl,

[0197] Oxadiazolyl,

[0198] Xanthyl,

[0199] Benzofuranyl,

[0200] Isobenzofuranyl,

[0201] Dibenzofuranyl,

[0202] Naphthobenzofuranyl,

[0203] Benzoxazolyl,

[0204] Benzisoxazolyl,

[0205] Phenoxazine,

[0206] Morpholino,

[0207] dinaphthofuranyl,

[0208] Azadibenzofuranyl,

[0209] Diazadibenzofuranyl,

[0210] azanaphthobenzofuranyl, and

[0211] naphthyridinylbenzofuranyl.

[0212] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0213] Thienyl,

[0214] Thiazolyl,

[0215] Isothiazolyl,

[0216] Thiadiazole,

[0217] benzothienyl,

[0218] Isobenzothienyl,

[0219] dibenzothienyl,

[0220] naphthobenzothienyl,

[0221] Benzothiazolyl,

[0222] Benzisothiazolyl,

[0223] Phenothiazine,

[0224] dinaphthothiophenyl,

[0225] azadibenzothienyl,

[0226] diazadibenzothienyl,

[0227] azanaphthobenzothienyl, and

[0228] diazanaphthobenzothienyl.

[0229] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0230] [Chemistry 4]

[0231]

[0232] [Chemistry 5]

[0233]

[0234] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A are each independently an oxygen atom, a sulfur atom, NH or CH 2 Among them, X A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0235] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A At least one of them is NH, or CH 2 When the monovalent heterocyclic group derived from the ring structure represented by the above general formula (TEMP-16) to (TEMP-33) includes the monovalent heterocyclic group derived from these NH or CH 2A monovalent group obtained by removing one hydrogen atom from a

[0236] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0237] (9-phenyl)carbazolyl,

[0238] (9-biphenyl)carbazolyl,

[0239] (9-phenyl)phenylcarbazolyl,

[0240] (9-naphthyl)carbazolyl,

[0241] Diphenylcarbazole-9-yl,

[0242] Phenylcarbazole-9-yl,

[0243] Methylbenzimidazolyl,

[0244] Ethylbenzimidazolyl,

[0245] Phenyl triazine,

[0246] Biphenyl triazine,

[0247] Diphenyltriazine,

[0248] Phenylquinazolinyl, and

[0249] Biphenylquinazolinyl.

[0250] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0251] Phenyldibenzofuranyl,

[0252] Methyldibenzofuranyl,

[0253] tert-Butyldibenzofuranyl, and

[0254] A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0255] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0256] Phenyldibenzothiophene,

[0257] Methyldibenzothiophene,

[0258] tert-Butyldibenzothienyl, and

[0259] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0260] A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced by a substituent (specific example group G2B4):

[0261] The aforementioned “one or more hydrogen atoms of a monovalent heterocyclic group” means one or more hydrogen atoms selected from hydrogen atoms bonded to ring-constituting carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of XA and YA is NH, and hydrogen atoms of a methylene group when one of XA and YA is CH2.

[0262] "Substituted or unsubstituted alkyl"

[0263] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when "alkyl" is mentioned alone, both "unsubstituted alkyl" and "substituted alkyl" are included.

[0264] "Substituted alkyl" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by substituents, and examples of substituted alkyl (specific example group G3B) can be cited. In the present specification, the alkyl group in "unsubstituted alkyl" means a chain alkyl group. Therefore, "unsubstituted alkyl" includes straight-chain "unsubstituted alkyl" and branched "unsubstituted alkyl". It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in the present specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of the specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkyl" of the specific example group G3B are further replaced by substituents.

[0265] Unsubstituted alkyl (specific example group G3A):

[0266] methyl,

[0267] Ethyl,

[0268] n-propyl,

[0269] Isopropyl,

[0270] n-Butyl,

[0271] Isobutyl,

[0272] sec-butyl, and

[0273] Tert-butyl.

[0274] Substituted alkyl (specific example group G3B):

[0275] Heptafluoropropyl (including isomers),

[0276] Pentafluoroethyl,

[0277] 2,2,2-Trifluoroethyl,

[0278] Trifluoromethyl.

[0279] "Substituted or unsubstituted alkenyl"

[0280] As specific examples of "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl (specific example group G4A), and substituted alkenyl (specific example group G4B) can be cited. (Here, unsubstituted alkenyl refers to the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In this specification, when "alkenyl" is mentioned alone, both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0281] "Substituted alkenyl" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) having a substituent, and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes a group in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent, and a group in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0282] Unsubstituted alkenyl (specific example group G4A):

[0283] Vinyl,

[0284] Allyl,

[0285] 1-Butenyl,

[0286] 2-Butenyl, and

[0287] 3-Butenyl.

[0288] Substituted alkenyl (specific example group G4B):

[0289] 1,3-Butadienyl,

[0290] 1-Methylvinyl,

[0291] 1-methylallyl,

[0292] 1,1-dimethylallyl,

[0293] 2-methylallyl, and

[0294] 1,2-Dimethylallyl.

[0295] "Substituted or unsubstituted alkynyl"

[0296] As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) Hereinafter, when "alkynyl" is mentioned alone, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

[0297] "Substituted alkynyl" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0298] Unsubstituted alkynyl (specific example group G5A):

[0299] Ethynyl.

[0300] "Substituted or unsubstituted cycloalkyl"

[0301] As specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6), the following unsubstituted cycloalkyl (specific example group G6A), and substituted cycloalkyl (specific example group G6B) can be cited. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when "cycloalkyl" is mentioned alone, both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0302] "Substituted cycloalkyl" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" recorded in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0303] Unsubstituted cycloalkyl (specific example group G6A):

[0304] Cyclopropyl,

[0305] Cyclobutyl,

[0306] Cyclopentyl,

[0307] Cyclohexyl,

[0308] 1-adamantyl,

[0309] 2-adamantyl,

[0310] 1-Norbornyl, and

[0311] 2-Norbornyl.

[0312] Substituted cycloalkyl (specific example group G6B):

[0313] 4-Methylcyclohexyl.

[0314] ·“-Si(R 901 )(R 902 )(R 903 )"

[0315] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are represented by (specific example group G7), and include:

[0316] -Si(G1)(G1)(G1),

[0317] -Si(G1)(G2)(G2),

[0318] -Si(G1)(G1)(G2),

[0319] -Si(G2)(G2)(G2),

[0320] -Si(G3)(G3)(G3), and

[0321] -Si(G6)(G6)(G6).

[0322] Here,

[0323] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0324] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0325] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0326] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0327] - A plurality of G1's in Si(G1)(G1)(G1) are the same as or different from each other.

[0328] - A plurality of G2's in Si(G1)(G2)(G2) are the same as or different from each other.

[0329] - A plurality of G1's in Si(G1)(G1)(G2) are the same as or different from each other.

[0330] - Multiple G2 in Si(G2)(G2)(G2) are the same as or different from each other.

[0331] - Multiple G3 in Si(G3)(G3)(G3) are the same as or different from each other.

[0332] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0333] ·“-O-(R 904 )"

[0334] As described in this specification, -O-(R 904 ) Specific examples of the group represented by (specific example group G8) include:

[0335] -O(G1),

[0336] -O(G2),

[0337] -O(G3), and

[0338] -O(G6).

[0339] Here,

[0340] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0341] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0342] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0343] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0344] ·“-S-(R 905 )"

[0345] As described in this specification, -S-(R 905 ) are represented by (specific example group G9), and include:

[0346] - S(G1),

[0347] - S(G2),

[0348] -S(G3), and

[0349] -S(G6).

[0350] Here,

[0351] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0352] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0353] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0354] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0355] ·“-N(R 906 )(R 907 )"

[0356] As described in this specification, -N(R 906 )(R 907 ) are represented by (specific example group G10):

[0357] -N(G1)(G1),

[0358] -N(G2)(G2),

[0359] -N(G1)(G2),

[0360] -N(G3)(G3), and

[0361] -N(G6)(G6).

[0362] Here,

[0363] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0364] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0365] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0366] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0367] - A plurality of G1 in N(G1)(G1) are the same as or different from each other.

[0368] - Multiple G2 in N(G2)(G2) are the same as or different from each other.

[0369] - Multiple G3 in N(G3)(G3) are the same as or different from each other.

[0370] - A plurality of G6's in N(G6)(G6) are the same as or different from each other.

[0371] "Halogen atoms"

[0372] Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0373] "Substituted or unsubstituted fluorinated alkyl"

[0374] The "substituted or unsubstituted fluoroalkyl group" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an 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 carbon atoms constituting an alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). Unless otherwise described in the present specification, the number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced by a substituent. It should be noted that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted fluoroalkyl group" are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted fluoroalkyl group" are further replaced by a substituent. Specific examples of the "unsubstituted fluorinated alkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0375] "Substituted or unsubstituted haloalkyl"

[0376] The "substituted or unsubstituted haloalkyl" described in the present specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl" is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in the "substituted or unsubstituted alkyl" are replaced by halogen atoms. Unless otherwise described in the present specification, the number of carbon atoms in the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl" means a group in which one or more hydrogen atoms of a "haloalkyl" are replaced by a substituent. It should be noted that the "substituted haloalkyl" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted haloalkyl" are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted haloalkyl" are further replaced by a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the aforementioned "alkyl" (specific example group G3) are replaced by halogen atoms. A haloalkyl group may be referred to as a halogenated alkyl group.

[0377] "Substituted or unsubstituted alkoxy"

[0378] A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise described in the present specification, the number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0379] "Substituted or unsubstituted alkylthio"

[0380] A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise described in the present specification, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms.

[0381] "Substituted or unsubstituted aryloxy"

[0382] A specific example of the "substituted or unsubstituted aryloxy group" described in the present specification is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise described in the present specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0383] "Substituted or unsubstituted arylthio group"

[0384] A specific example of the "substituted or unsubstituted arylthio group" described in the present specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise described in the present specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0385] "Substituted or unsubstituted trialkylsilyl"

[0386] A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same or different from each other. Unless otherwise described in the present specification, 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.

[0387] "Substituted or unsubstituted aralkyl"

[0388] A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

[0389] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0390] Unless otherwise described in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.

[0391] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthiobenzofuranyl group, a benzothiophenyl ... benzothiophenyl 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-biphenyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazine group, biphenyltriazine group, diphenyltriazine group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.

[0392] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

[0393] [Chemistry 6]

[0394]

[0395] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0396] [Chemistry 7]

[0397]

[0398] In the aforementioned general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding site.

[0399] In the present specification, the dibenzofuranyl group and the dibenzothienyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0400] [Chemistry 8]

[0401]

[0402] In the aforementioned general formulae (TEMP-34) to (TEMP-41), * represents a bonding site.

[0403] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like.

[0404] "Substituted or unsubstituted arylene group"

[0405] 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 aromatic ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aromatic ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

[0406] · "Substituted or unsubstituted divalent heterocyclic group"

[0407] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom on the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom on the heterocyclic ring.

[0408] "Substituted or unsubstituted alkylene"

[0409] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

[0410] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0411] [Chemistry 9]

[0412]

[0413] [Chemistry 10]

[0414]

[0415] In the above general formulas (TEMP-42) to (TEMP-52), Q 1 ~Q 10 Each is independently a hydrogen atom or a substituent.

[0416] In the aforementioned general formulae (TEMP-42) to (TEMP-52), * represents a bonding site.

[0417] [Chemistry 11]

[0418]

[0419] In the above general formulas (TEMP-53) to (TEMP-62), Q 1 ~Q 10 Each is independently a hydrogen atom or a substituent.

[0420] Formula Q 9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0421] In the aforementioned general formulae (TEMP-53) to (TEMP-62), * represents a bonding site.

[0422] [Chemistry 12]

[0423]

[0424] In the above general formulas (TEMP-63) to (TEMP-68), Q 1 ~Q 8 Each is independently a hydrogen atom or a substituent.

[0425] In the aforementioned general formulae (TEMP-63) to (TEMP-68), * represents a bonding site.

[0426] Unless otherwise described in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102).

[0427] [Chemistry 13]

[0428]

[0429] [Chemistry 14]

[0430]

[0431] [Chemistry 15]

[0432]

[0433] In the above general formulas (TEMP-69) to (TEMP-82), Q 1 ~Q 9 Each is independently a hydrogen atom or a substituent.

[0434] [Chemistry 16]

[0435]

[0436] [Chemistry 17]

[0437]

[0438] [Chemistry 18]

[0439]

[0440] [Chemistry 19]

[0441]

[0442] In the above general formulas (TEMP-83) to (TEMP-102), Q 1 ~Q 8 Each is independently a hydrogen atom or a substituent.

[0443] The above is the description of the “substituents described in the present specification”.

[0444] "Bonds forming a ring"

[0445] In the present specification, the situation that "one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means the situation that "one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring", the situation that "one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring", and the situation that "one or more groups consisting of two or more adjacent groups are not bonded to each other".

[0446] Hereinafter, the case of "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" in this specification (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring") are explained. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring is explained as an example.

[0447] [Chemistry 20]

[0448]

[0449] For example, R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent groups are bonded to each other to form a ring", one group consisting of two adjacent groups is R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0450] The above “one or more groups” means that two or more groups consisting of two or more adjacent groups can simultaneously form a ring. 921 With R 922 Bonded to each other to form ring Q A And at the same time R 925 With R 926 Bonded to each other to form ring Q B In the case of, the anthracene compound represented by the aforementioned general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0451] [Chemistry 21]

[0452]

[0453] The case where "a group of two or more adjacent members" forms a ring includes not only the case where the adjacent "two" members are bonded as in the above example, but also the case where the adjacent "three or more" members are bonded. For example, R 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and fused to form an anthracene mother 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 Total R 922 .

[0454] [Chemistry 22]

[0455]

[0456] The "monocyclic ring" or "condensed ring" formed as a structure of the ring formed alone may be a saturated ring or an unsaturated ring. Even when "a group consisting of two adjacent groups" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and Ring Q B Each is a "monocyclic" or "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A and Ring Q C The ring Q of the above general formula (TEMP-105) is a "condensed ring". A With Ring Q C By RingQ A With Ring Q C The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0457] The "unsaturated ring" includes, in addition to aromatic hydrocarbon rings and aromatic heterocyclic rings, aliphatic hydrocarbon rings having unsaturated bonds, i.e., double bonds and / or triple bonds in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocyclic rings having unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The "saturated ring" includes aliphatic hydrocarbon rings without unsaturated bonds, or non-aromatic heterocyclic rings without unsaturated bonds.

[0458] Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0459] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0460] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0461] "Forming a ring" means that a ring is formed only by a plurality of atoms of the parent skeleton, or by a plurality of atoms of the parent skeleton and one or more arbitrary atoms. For example, R 921 With R 922 The ring Q formed by mutual bonding A Meaning by R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922As a specific example, in the case where R 921 With R 922 Ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0462] Here, "any atom" is preferably at least one atom selected from carbon atom, nitrogen atom, oxygen atom and sulfur atom unless otherwise described in this specification. For any atom (such as carbon atom or nitrogen atom), the bond that does not form a ring may be terminated by hydrogen atom or the like, or may be substituted by "any substituent" described later. When any atom other than carbon atom is included, the formed ring is a heterocycle.

[0463] Unless otherwise specified in the present specification, the number of "one or more arbitrary atoms" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0464] Unless otherwise specified in the present specification, "monocyclic ring" is preferred over "monocyclic ring" and "condensed ring".

[0465] In the present specification, unless otherwise specified, of "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0466] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0467] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0468] In the case of "one or more groups consisting of two or more adjacent groups" "bonded to each other to form a substituted or unsubstituted monocyclic ring", or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise stated in the present specification, it is preferred that one or more groups consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and one or more and fifteen or less atoms selected from carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

[0469] 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 above-mentioned "substituents described in the present specification".

[0470] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0471] The above is an explanation of the case where "one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0472] ·Substituents in the case of "substituted or unsubstituted"

[0473] In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, a group selected from the following:

[0474] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0475] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0476] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0477] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0478] -Si(R 901 )(R 902 )(R 903 ),

[0479] -O-(R 904 ),

[0480] -S-(R 905 ),

[0481] -N(R 906 )(R 907 ),

[0482] Halogen atoms, cyano, nitro,

[0483] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0484] An unsubstituted heterocyclic group having 5 to 50 ring atoms;

[0485] Here, R 901 ~R 907 Each independently is:

[0486] Hydrogen atoms,

[0487] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0488] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0489] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0490] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0491] R 901 When there are two or more, two or more R 901 Same or different from each other,

[0492] R 902 When there are two or more, two or more R 902 Same or different from each other,

[0493] R 903 When there are two or more, two or more R 903 Same or different from each other,

[0494] R 904 When there are two or more, two or more R 904 Same or different from each other,

[0495] R 905 When there are two or more, two or more R 905 Same or different from each other,

[0496] R 906 When there are two or more, two or more R 906 Same or different from each other,

[0497] R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0498] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0499] Alkyl groups having 1 to 50 carbon atoms,

[0500] an aryl group having 6 to 50 ring carbon atoms, and

[0501] A heterocyclic group having 5 to 50 ring atoms.

[0502] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0503] Alkyl groups having 1 to 18 carbon atoms,

[0504] an aryl group having 6 to 18 ring carbon atoms, and

[0505] A heterocyclic group having 5 to 18 ring atoms.

[0506] Specific examples of each of the above-mentioned optional substituents are the same as the specific examples of the substituents described in the above section "Substituents described in the present specification".

[0507] Unless otherwise stated in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming 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, more preferably forming a benzene ring.

[0508] Unless otherwise specified in the present specification, an arbitrary substituent may further have a substituent. The substituent further possessed by the arbitrary substituent is the same as the above-mentioned arbitrary substituent.

[0509] In this specification, the numerical range using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0510] [Novel Compounds]

[0511] The compound according to one embodiment of the present invention is represented by the following formula (1).

[0512] [Chemistry 23]

[0513]

[0514] In formula (1),

[0515] X 1 and X 2 are each independently N or CH, X 1 and X 2 Any one of them is N.

[0516] Ar 1 and Ar 2 Each independently is:

[0517] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0518] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0519] L 1 ~L 3 Each independently is:

[0520] single bond,

[0521] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0522] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0523] n1 is an integer from 0 to 4. When n1 is 0, (L 1 ) n1 is a single bond. 1 When there are multiple L 1 Each may be the same or different.

[0524] n2 is an integer from 0 to 4. When n2 is 0, (L 2 ) n2 is a single bond. 2 When there are multiple L 2 Each may be the same or different.

[0525] n3 is an integer of 0 to 4. When n3 is 0, (L 3 ) n3 is a single bond. 3 When there are multiple L 3 Each may be the same or different.

[0526] R 11 ~R 19 Each independently is a hydrogen atom or a substituent R; 11 ~R 19 The adjacent groups of two or more are not bonded to each other.

[0527] R 21 and R 22 They may bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[0528] The aforementioned R which does not form a substituted or unsubstituted saturated or unsaturated ring 21 and R 22 Each independently is:

[0529] Hydrogen atoms,

[0530] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0531] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0532] The substituent R is selected from:

[0533] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0534] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0535] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0536] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0537] -Si(R 901 )(R 902 )(R 903 ),

[0538] -O-(R 904 ),

[0539] -S-(R 905 ),

[0540] -N(R 906 )(R 907 ),

[0541] Halogen atoms, cyano, nitro,

[0542] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0543] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0544] R 901 ~R 907 Each independently is:

[0545] Hydrogen atoms,

[0546] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0547] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0548] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0549] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0550] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 Each may be the same or different.

[0551] When there are two or more substituents R, the two or more substituents R may be the same or different.

[0552] In formula (1), X 1 and X 2 One of them is N and the other is CH. That is, X1 When N, X 2 For CH. 2 When N, X 1 For CH.

[0553] In formula (1), L 1 When there are multiple (n1 is 2 or more), Ar 1 With X 1 and X 2 The nitrogen-containing six-membered ring is farthest from L 1 Bonding. 2 When there are multiple (when n2 is 2 or more), Ar 2 and distance including X 1 and X 2 The farthest L of the nitrogen-containing six-membered ring 2 Bonding. 3 When there are multiple benzofluorene skeletons (when n3 is 2 or more), the distance between the benzofluorene skeleton and the benzofluorene skeleton is 1. 1 and X 2 The farthest L of the nitrogen-containing six-membered ring 3 Bonding.

[0554] For example, when n1 is 2, n2 is 3, and n3 is 2, the compound represented by formula (1) has the following structure. 1 and X 2 The nitrogen-containing six-membered ring" is represented as ring α.

[0555] [Chemistry 24]

[0556]

[0557] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (11).

[0558] [Chemistry 25]

[0559]

[0560]

[0561] X 1 , X 2 ,Ar 1 ,Ar 2 , L 1 , L 2 、n1、n2、R 11 ~R 19 , R 21 and R 22 As defined in the above formula (1).

[0562] In one embodiment, R in formula (11)21 and R 22 A substituted or unsubstituted saturated or unsaturated ring is not formed.

[0563] In one embodiment, R in formula (11) 21 and R 22 It is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0564] In one embodiment, R in formula (11) 21 and R 22 It is methyl.

[0565] In one embodiment, X in formula (11) 1 N, X 2 For CH.

[0566] In one embodiment, the compound represented by the above formula (11) is a compound represented by any one of the following formulas (111) to (113).

[0567] [Chemistry 26]

[0568]

[0569] [Chemistry 27]

[0570]

[0571] In formula (111), L 1 , L 2 , n1, n2 and R 11 ~R 19 As defined in the above formula (1).

[0572] R 111 ~R 120 Each is independently a hydrogen atom or a substituent R. 111 ~R 120 The adjacent groups of two or more are not bonded to each other.

[0573] In formula (112),

[0574] L 1 , L 2 , n1, n2 and R 11 ~R 19 As defined in the above formula (1).

[0575] Y 1 N(R 129 )、C(R 130a )(R 130b ), O or S.

[0576] R 121 ~R129 Any of the above indicates that 2 key.

[0577] Not indicated with L 2 The key of R 121 ~R 129 Each independently represents a hydrogen atom or a substituent R. 2 The key of R 121 ~R 129 The adjacent groups of two or more are not bonded to each other.

[0578] R 130a and R 130b They may bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or may not form a substituted or unsubstituted saturated or unsaturated ring.

[0579] The aforementioned R which does not form a substituted or unsubstituted saturated or unsaturated ring 130a and R 130b Each is independently a hydrogen atom or a substituent R.

[0580] R 131 ~R 135 Each is independently a hydrogen atom or a substituent R. 131 ~R 135 The adjacent groups of two or more are not bonded to each other.

[0581] In formula (113),

[0582] L 1 , L 2 , n1, n2 and R 11 ~R 19 As defined in the above formula (1).

[0583] R 141 ~R 150 Any of the above indicates that 2 key.

[0584] Not indicated with L 2 The key of R 141 ~R 150 Each independently represents a hydrogen atom or a substituent R. 2 The key of R 141 ~R 150 The adjacent groups of two or more are not bonded to each other.

[0585] R 151 ~R 155 Each is independently a hydrogen atom or a substituent R. 151 ~R 155 The adjacent groups of two or more are not bonded to each other.

[0586] The substituent R is as defined above in formula (1).

[0587] In one embodiment, R in formula (112) 123 Indicates that L 2 key.

[0588] R 123 Indicates that L 2 When the bond is , the compound represented by formula (112) becomes the following structure.

[0589] [Chemistry 28]

[0590]

[0591] In one embodiment, Y 1 is O.

[0592] In one embodiment, R in formula (113) 141 , R 143 or R 149 Indicates that L 2 key.

[0593] In one embodiment, X in formula (11) 1 CH, X 2 is N.

[0594] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (21).

[0595] [Chemistry 29]

[0596]

[0597] In formula (21),

[0598] X 1 , X 2 ,Ar 1 ,Ar 2 , L 1 , L 2 、n1、n2、R 11 ~R 19 , R 21 and R 22 As defined in the above formula (1).

[0599] L 21 for:

[0600] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0601] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[0602] n21 is an integer from 1 to 4. 21 When there are multiple L 21 Each may be the same or different.

[0603] In one embodiment, R in formula (21) 21 and R 22 A substituted or unsubstituted saturated or unsaturated ring is not formed.

[0604] In one embodiment, R in formula (21) 21 and R 22 It is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0605] In one embodiment, R in formula (21) 21 and R 22 It is methyl.

[0606] In one embodiment, L in formula (21) 21 It is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0607] In one embodiment, L in formula (21) 21 It is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0608] In one embodiment, X in formula (21) 1 N, X 2 For CH.

[0609] In one embodiment, the compound represented by the above formula (21) is a compound represented by the following formula (211) or formula (212).

[0610] [Chemistry 30]

[0611]

[0612] In formula (211),

[0613] Ar 1 ,Ar 2 , L 1 , L 2 , n1, n2 and R 11 ~R 19 As defined in the above formula (1).

[0614] R 211 ~R 214 Each is independently a hydrogen atom or a substituent R. 211 ~R 214 The adjacent groups of two or more are not bonded to each other.

[0615] In formula (212),

[0616] Ar 1 ,Ar 2 , L 1 , L 2 , n1, n2 and R 11 ~R 19 As defined in the above formula (1).

[0617] R 221 ~R 226 Each is independently a hydrogen atom or a substituent R. 221 ~R 226 The adjacent groups of two or more are not bonded to each other.

[0618] The substituent R is as defined above in formula (1).

[0619] In one embodiment, X in formula (21) 1 For CH, X 2 is N.

[0620] In one embodiment, the compound represented by the above formula (21) is a compound represented by the following formula (221) or formula (222).

[0621] [Chemistry 31]

[0622]

[0623] In formula (221),

[0624] Ar 1 ,Ar 2 , L 1 , L 2 , n1, n2 and R 11 ~R 19 As defined in the above formula (1).

[0625] R 211 ~R 214 Each is independently a hydrogen atom or a substituent R. 211 ~R 214 The adjacent groups of two or more are not bonded to each other.

[0626] In formula (222),

[0627] Ar 1 ,Ar 2 , L 1 , L 2 , n1, n2 and R 11 ~R 19 As defined in the above formula (1).

[0628] R 221 ~R 226 Each is independently a hydrogen atom or a substituent R. 221 ~R 226 The adjacent groups of two or more are not bonded to each other.

[0629] The substituent R is as defined above in formula (1).

[0630] In one embodiment, Ar in formula (21) 1 and Ar 2 Each is independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

[0631] In one embodiment, Ar in formula (21) 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0632] In one embodiment, L in formula (1) 1 and L 2 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0633] In one embodiment, R in formula (1) 11 ~R 19 A hydrogen atom.

[0634] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) and the substituent R are selected from the following groups: an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms.

[0635] In one embodiment, the substituent in the case of "substituted or unsubstituted" in formula (1) and the substituent R are selected from the following groups: an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring atoms.

[0636] In one embodiment, the compound represented by formula (1) has at least one deuterium atom as a hydrogen atom in the molecule.

[0637] In this specification, "having deuterium atoms as hydrogen atoms" means that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms in the hydrogen atoms is greater than that in nature. It can be confirmed by a nuclear magnetic resonance device that the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is greater than that in nature.

[0638] In one embodiment, the compound represented by formula (1) does not have a deuterium atom as a hydrogen atom in the molecule.

[0639] In this specification, "does not have deuterium atoms as hydrogen atoms" means that among all hydrogen atoms in the molecule, the ratio of deuterium atoms to the total of protium atoms and deuterium atoms is less than the naturally occurring ratio. In other words, the compound represented by formula (1) that does not have deuterium atoms as hydrogen atoms in the molecule may contain deuterium atoms at a ratio less than the naturally occurring ratio.

[0640] The presence of protium atoms can be confirmed by nuclear magnetic resonance.

[0641] In one embodiment, Ar in formula (1) 1 It has at least one deuterium atom as a hydrogen atom.

[0642] In one embodiment, Ar in formula (1) 2 It has at least one deuterium atom as a hydrogen atom.

[0643] In one embodiment, L in formula (1) 3 It has at least one deuterium atom as a hydrogen atom.

[0644] In one embodiment, the hydrogen atom in formula (1), i.e., R 11 ~R 19 , R 21 and R 22 , and R as a substituent R 11 ~R 19 , R 21 and R 22 At least one of the hydrogen atoms present is a deuterium atom.

[0645] In one embodiment, L in formula (1) 23 There are no deuterium atoms as hydrogen atoms.

[0646] In one embodiment, the hydrogen atom in formula (1), i.e., R 11 ~R 19 , and R as a substituent R 11 ~R 19 The hydrogen atoms it has are protium atoms.

[0647] In one embodiment, R in formula (1) 21 and R 22 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, wherein R 21 and R 22 The hydrogen atoms it has are protium atoms.

[0648] The compound represented by formula (1) can be synthesized according to the Examples by using known substitution reactions and starting materials corresponding to the target compound.

[0649] Although specific examples of the compound represented by formula (1) are described below, these are merely illustrative and the compound represented by formula (1) is not limited to the following specific examples.

[0650] [Chemistry 32]

[0651]

[0652] [Chemistry 33]

[0653]

[0654] [Chemistry 34]

[0655]

[0656] [Chemistry 35]

[0657]

[0658] [Chemistry 36]

[0659]

[0660] [Chemistry 37]

[0661]

[0662] [Chemistry 38]

[0663]

[0664] [Chemistry 39]

[0665]

[0666] [Chemistry 40]

[0667]

[0668] [Chemistry 41]

[0669]

[0670] [Chemistry 42]

[0671]

[0672] [Chemistry 43]

[0673]

[0674] [Chemistry 44]

[0675]

[0676] [Chemistry 45]

[0677]

[0678] [Chemistry 46]

[0679]

[0680] [Chemistry 47]

[0681]

[0682] [Chemistry 48]

[0683]

[0684] [Chemistry 49]

[0685]

[0686] [Chemistry 50]

[0687]

[0688] [Chemistry 51]

[0689]

[0690] [Chemistry 52]

[0691]

[0692] [Chemistry 53]

[0693]

[0694] [Chemistry 54]

[0695]

[0696] [Chemistry 55]

[0697]

[0698] [Chemistry 56]

[0699]

[0700] [Chemistry 57]

[0701]

[0702] [Chemistry 58]

[0703]

[0704] [Chemistry 59]

[0705]

[0706] [Chemistry 60]

[0707]

[0708] [Chemistry 61]

[0709]

[0710] [Chemistry 62]

[0711]

[0712] [Chemistry 63]

[0713]

[0714] [Chemistry 64]

[0715]

[0716] [Chemistry 65]

[0717]

[0718] [Chemistry 66]

[0719]

[0720] [Chemistry 67]

[0721]

[0722] [Chemistry 68]

[0723]

[0724] [Chemistry 69]

[0725]

[0726] [Chemistry 70]

[0727]

[0728] [Chemistry 71]

[0729]

[0730] [Chemistry 72]

[0731]

[0732] [Chemistry 73]

[0733]

[0734] [Chemistry 74]

[0735]

[0736] [Chemistry 75]

[0737]

[0738] [Chemistry 76]

[0739]

[0740] [Chemistry 77]

[0741]

[0742] [Chemistry 78]

[0743]

[0744] [Chemistry 79]

[0745]

[0746] [Chemistry 80]

[0747]

[0748] [Chemistry 81]

[0749]

[0750] [Chemistry 82]

[0751]

[0752] [Chemistry 83]

[0753]

[0754] [Chemistry 84]

[0755]

[0756] [Chemistry 85]

[0757]

[0758] [Chemistry 86]

[0759]

[0760] [Chemistry 87]

[0761]

[0762] [Chemistry 88]

[0763]

[0764] [Chemistry 89]

[0765]

[0766] [Chemistry 90]

[0767]

[0768] [Chemistry 91]

[0769]

[0770] [Chemistry 92]

[0771]

[0772] [Chemistry 93]

[0773]

[0774] [Chemistry 94]

[0775]

[0776] [Chemistry 95]

[0777]

[0778] [Chemistry 96]

[0779]

[0780] [Chemistry 97]

[0781]

[0782] [Chemistry 98]

[0783]

[0784] [Chemistry 99]

[0785]

[0786] [Chemical 100]

[0787]

[0788] [Chemistry 101]

[0789]

[0790] [Chemistry 102]

[0791]

[0792] [Chemistry 103]

[0793]

[0794] [Chemistry 104]

[0795]

[0796] [Chemistry 105]

[0797]

[0798] [Chemistry 106]

[0799]

[0800] [Chemistry 107]

[0801]

[0802] [Chemistry 108]

[0803]

[0804] [Chemistry 109]

[0805]

[0806] [Chemistry 110]

[0807]

[0808] [Chemistry 111]

[0809]

[0810] [Chemistry 112]

[0811]

[0812] [Chemistry 113]

[0813]

[0814] [Chemistry 114]

[0815]

[0816] [Chemistry 115]

[0817]

[0818] [Chemistry 116]

[0819]

[0820] [Chemistry 117]

[0821]

[0822] [Chemistry 118]

[0823]

[0824] [Chemistry 119]

[0825]

[0826] [Chemistry 120]

[0827]

[0828] [Chemistry 121]

[0829]

[0830] [Chemistry 122]

[0831]

[0832] [Chemistry 123]

[0833]

[0834] [Chemistry 124]

[0835]

[0836] [Chemistry 125]

[0837]

[0838] [Chemistry 126]

[0839]

[0840] [Chemistry 127]

[0841]

[0842] [Chemistry 128]

[0843]

[0844] [Chemistry 129]

[0845]

[0846] [Chemistry 130]

[0847]

[0848] [Chemistry 131]

[0849]

[0850] [Chemistry 132]

[0851]

[0852] [Chemistry 133]

[0853]

[0854] [Chemistry 134]

[0855]

[0856] [Chemistry 135]

[0857]

[0858] [Materials for organic electroluminescent devices]

[0859] The compound of one embodiment of the present invention can be used as a material for an organic EL device, for example, can be used as a material used in an electron transport region of an organic EL device.

[0860] [Organic EL element]

[0861] An organic EL element according to one embodiment of the present invention will be described.

[0862] An organic EL element according to one embodiment of the present invention comprises: a cathode, an anode, and one or more organic layers disposed between the cathode and the anode; at least one of the organic layers comprises a compound according to one embodiment of the present invention (compound represented by formula (1)).

[0863] In one embodiment, an organic EL device according to one embodiment of the present invention includes an anode, a light-emitting layer, an electron-transporting region, and a cathode in this order, and the electron-transporting region includes the compound according to one embodiment of the present invention (compound represented by formula (1)).

[0864] In one embodiment, the electron transport region comprises a first layer (also referred to as a "first electron transport layer" or a "hole barrier layer") and a second layer (also referred to as a "second electron transport layer") in order from the light-emitting layer side, and the first layer comprises a compound represented by formula (1). As the second layer in this case, for example, the structure of the electron transport layer described later can be applied.

[0865] As a typical element structure of this organic EL element, there can be exemplified a structure in which the following structures are stacked on a substrate.

[0866] (1) Anode / light-emitting layer / electron transport region / cathode

[0867] (2) Anode / hole transport region / light-emitting layer / electron transport region / cathode

[0868] (“ / ” indicates that the layers are adjacent and stacked.)

[0869] The electron transport region generally includes one or more layers selected from the group consisting of an electron injection layer and an electron transport layer. The hole transport region generally includes one or more layers selected from the group consisting of a hole injection layer and a hole transport layer.

[0870] Reference Figure 1 A schematic configuration of an organic EL element according to one embodiment of the present invention will be described.

[0871] An organic EL element 1 according to one embodiment of the present invention includes a substrate 2 , an anode 3 , a light-emitting layer 5 , a cathode 10 , a hole transport region 4 between the anode 3 and the light-emitting layer 5 , and an electron transport region 6 between the light-emitting layer 5 and the cathode 10 .

[0872] Hereinafter, members that can be used in the organic EL element of one embodiment of the present invention and materials other than the above-mentioned compounds constituting each layer will be described.

[0873] (Substrate)

[0874] The substrate is used as a support for the light-emitting element. As the substrate, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can also be used. A flexible substrate refers to a bendable (flexible) substrate, and examples thereof include a plastic substrate formed of polycarbonate or polyvinyl chloride.

[0875] (anode)

[0876] The anode formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include: indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), or nitrides of metal materials (for example, titanium nitride) can also be mentioned.

[0877] (Hole Injection Layer)

[0878] The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.

[0879] (Hole Transport Layer)

[0880] The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used in the hole transport layer. Polymer compounds such as poly (N-vinyl carbazole) (abbreviated as: PVK) and poly (4-vinyl triphenylamine) (abbreviated as: PVTPA) can also be used. Among them, as long as the hole transport property is higher than the electron transport property, substances other than the above can be used. It should be noted that the layer containing a substance with high hole transport properties can be not only a single-layer layer, but also a layer formed by stacking two or more layers containing the above substances.

[0881] (Guest (dopant) material of the light-emitting layer)

[0882] The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as a highly luminescent substance, a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.

[0883] As the blue fluorescent material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. As green fluorescent luminescent materials that can be used in the luminescent layer, aromatic amine derivatives, etc. can be used. As red fluorescent luminescent materials that can be used in the luminescent layer, butane derivatives, diamine derivatives, etc. can be used.

[0884] As the blue phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complex, osmium complex, and platinum complex are used. As the green phosphorescent material that can be used in the light-emitting layer, iridium complex is used. As the red phosphorescent material that can be used in the light-emitting layer, metal complexes such as iridium complex, platinum complex, terbium complex, and europium complex are used.

[0885] (Host material of light-emitting layer)

[0886] As the light-emitting layer, the composition can be made by dispersing the above-mentioned high-luminescent substance (guest material) in other substances (host material). As the material for dispersing the high-luminescent substance, various substances can be used, preferably a substance having a high minimum unoccupied orbital energy level (LUMO energy level) and a low maximum occupied orbital energy level (HOMO energy level) compared with the high-luminescent substance.

[0887] As the substance (host material) for dispersing the highly luminescent substance, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or 4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[0888] (Electron Transport Layer)

[0889] The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can use: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, oxazine derivatives, carbazole derivatives, and phenanthroline derivatives; 3) polymer compounds.

[0890] In one embodiment of the present invention, the electron transport layer may or may not contain the above-mentioned other substances in addition to the compound of one embodiment of the present invention (the compound represented by formula (1)).

[0891] (Electron Injection Layer)

[0892] The electron injection layer is a layer containing a substance with high electron injection properties. Lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), metal complex compounds such as 8-hydroxyquinoline-lithium (Liq), lithium oxide (LiO x ) or other alkali metals, alkaline earth metals, or compounds thereof.

[0893] (cathode)

[0894] The cathode preferably uses a metal, alloy, conductive compound, and mixtures thereof with a small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys thereof.

[0895] The cathode is usually formed by vacuum deposition or sputtering. When silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

[0896] When an electron injection layer is provided, the cathode can be formed using various conductive materials such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function.

[0897] In the organic EL device according to one embodiment of the present invention, the thickness of each layer is not particularly limited, but is generally preferably in the range of several nm to 1 μm in order to suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency.

[0898] In the organic EL element involved in one embodiment of the present invention, the method for forming each layer is not particularly limited. A conventionally known formation method based on vacuum evaporation, spin coating, etc. can be used. Each layer such as the light-emitting layer can be formed by a known method based on a coating method such as vacuum evaporation, molecular beam evaporation (MBE), or a solution dissolved in a solvent, such as dipping, spin coating, casting, rod coating, and roller coating.

[0899] [Electronic equipment]

[0900] An electronic device according to one embodiment of the present invention is characterized by including the organic EL element according to one embodiment of the present invention.

[0901] Specific examples of electronic devices include display components such as organic EL panel modules; display devices such as televisions, mobile phones, and personal computers; and light-emitting devices such as lighting or vehicle lamps.

[0902] Example

[0903] <Compound>

[0904] The compound represented by formula (1) used for producing the organic EL device in the example is shown below.

[0905] [Chemistry 136]

[0906]

[0907] [Chemistry 137]

[0908]

[0909] The compounds used in the production of the organic EL device of the comparative example are shown below.

[0910] [Chemistry 138]

[0911]

[0912] Other compounds used in the production of the organic EL devices of Examples and Comparative Examples are shown below.

[0913] [Chemistry 139]

[0914]

[0915] [Chemistry 140]

[0916]

[0917] Example 1

[0918] <Production of organic EL elements>

[0919] An organic EL device was produced as follows.

[0920] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to make the ITO film thickness 130 nm.

[0921] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation device. First, compounds HTL-1 and HI-1 were co-evaporated on the surface on which the transparent electrode was formed so as to cover the transparent electrode in a manner that the ratio of compound HI-1 was 3% by mass, thereby forming a hole injection layer with a film thickness of 10 nm.

[0922] Compound HTL-1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[0923] Compound EBL-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 5 nm.

[0924] On the second hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated so that the ratio of compound BD-1 was 1 mass %, thereby forming a 20 nm thick light emitting layer.

[0925] Compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer (hole barrier layer) with a thickness of 5 nm.

[0926] On the first electron transport layer, the compound ETL-1 and Liq were co-evaporated so that the ratio of Liq became 50 mass %, thereby forming a second electron transport layer having a film thickness of 25 nm.

[0927] Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[0928] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0929] The device structure of the organic EL device of Example 1 is briefly shown below.

[0930] ITO(130) / HTL-1:HI-1(10:3%) / HTL-1(80) / EBL-1(5) / BH-1:BD-1(20:1%) / ET-1(5) / ETL-1:Liq(25:50%) / Yb(1) / Al(80)

[0931] The numbers in parentheses indicate the film thickness (unit: nm). In addition, the numbers in parentheses expressed as percentages indicate the ratio (mass %) of the latter compound in the layer.

[0932] <Evaluation of organic EL elements>

[0933] The produced organic EL device was evaluated as follows.

[0934] External quantum efficiency (EQE)

[0935] At a current density of 10 mA / cm 2 A voltage was applied to the organic EL element in a manner of , and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Conika Minolta Co., Ltd.). EQE (%) was calculated from the obtained spectroradiometric brightness spectrum. In Table 1, EQE ratio (%) represents a relative value when Comparative Example 1 described later is set to 100.

[0936] Examples 2 to 18, Comparative Example 1

[0937] The organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compound described in Table 1 was used instead of ET-1.

[0938] [Table 1]

[0939] First electron transport layer EQE(%) EQE ratio (%) Example 1 ET-1 10.1 110 Example 2 ET-2 10.0 110 Example 3 ET-3 9.7 107 Example 4 ET-5 10.0 110 Example 5 ET-6 10.1 111 Example 6 ET-7 10.0 110 Example 7 ET-8 9.7 106 Example 8 ET-9 10.1 111 Example 9 ET-10 10.1 110 Example 10 ET-11 10.1 111 Embodiment 11 ET-12 10.1 111 Example 12 ET-13 10.0 110 Embodiment 13 ET-14 9.9 109 Embodiment 14 ET-15 9.7 107 Embodiment 15 ET-16 9.8 108 Example 16 ET-17 9.8 108 Embodiment 17 ET-18 10.1 110 Embodiment 18 ET-19 10.1 111 Comparative Example 1 ET-Ref1 9.1 100

[0940] Embodiment 19

[0941] <Production of organic EL elements>

[0942] An organic EL device was produced as follows.

[0943] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to make the ITO film thickness 130 nm.

[0944] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation device. First, compounds HTL-2 and HI-1 were co-evaporated on the surface on which the transparent electrode was formed so as to cover the transparent electrode in a manner that the ratio of compound HI-1 was 3% by mass, thereby forming a hole injection layer with a thickness of 10 nm.

[0945] Compound HTL-2 was evaporated on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[0946] Compound EBL-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 5 nm.

[0947] On the second hole transport layer, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated so that the ratio of compound BD-1 was 1 mass %, thereby forming a 20 nm thick light emitting layer.

[0948] Compound ET-6 was evaporated on the light-emitting layer to form a first electron transport layer (hole barrier layer) with a thickness of 5 nm.

[0949] On the first electron transport layer, the compound ETL-1 and Liq were co-evaporated so that the ratio of Liq became 50 mass %, thereby forming a second electron transport layer having a film thickness of 25 nm.

[0950] Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[0951] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0952] The device structure of the organic EL device of Example 19 is briefly shown below.

[0953] ITO(130) / HTL-2:HI-1(10:3%) / HTL-2(80) / EBL-1(5) / BH-1:BD-1(20:1%) / ET-6(5) / ETL-1:Liq(25:50%) / Yb(1) / Al(80)

[0954] The numbers in parentheses indicate the film thickness (unit: nm). In addition, the numbers in parentheses expressed as percentages indicate the ratio (mass %) of the latter compound in the layer.

[0955] <Evaluation of organic EL elements>

[0956] The produced organic EL device was evaluated in the same manner as in Example 1. The results are shown in Table 2. In Table 2, the EQE ratio represents a relative value when Comparative Example 2 described later is set as 100.

[0957] Examples 20-21, Comparative Example 2

[0958] The organic EL device was prepared and evaluated in the same manner as in Example 19 except that the compound described in Table 2 was used instead of ET-6.

[0959] [Table 2]

[0960] First electron transport layer EQE(%) EQE ratio (%) Embodiment 19 ET-6 10.2 109 Embodiment 20 ET-7 10.1 107 Embodiment 21 ET-9 10.3 110 Comparative Example 2 ET-Ref2 9.4 100

[0961] Embodiment 22

[0962] <Fabrication of Organic EL Devices>

[0963] An organic EL device was produced as follows.

[0964] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatech Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to make the ITO film thickness 130 nm.

[0965] The cleaned glass substrate with a transparent electrode is mounted on a substrate holder of a vacuum evaporation device. First, on the surface on which the transparent electrode is formed, compounds HTL-1 and HI-1 are co-evaporated in a manner that covers the transparent electrode so that the ratio of compound HI-1 reaches 3% by mass, thereby forming a hole injection layer with a film thickness of 10 nm.

[0966] Compound HTL-3 was evaporated on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.

[0967] Compound EBL-1 was evaporated on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[0968] On the second hole transport layer, compound BH-2 (host material) and compound BD-1 (dopant material) were co-evaporated so that the ratio of compound BD-1 was 1 mass % to form a 20 nm thick light emitting layer.

[0969] Compound ET-4 was evaporated on the light-emitting layer to form a first electron transport layer (hole barrier layer) with a thickness of 5 nm.

[0970] On the first electron transport layer, the compound ETL-1 and Liq were co-evaporated so that the ratio of Liq became 50 mass %, thereby forming a second electron transport layer having a film thickness of 25 nm.

[0971] Metal Yb was evaporated on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[0972] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[0973] The device structure of the organic EL device of Example 22 is briefly shown as follows.

[0974] ITO(130) / HTL-1:HI-1(10:3%) / HTL-3(80) / EBL-1(5) / BH-2:BD-1(20:1%) / ET-4(5) / ETL-1:Liq(25:50%) / Yb(1) / A1(80)

[0975] The numbers in parentheses indicate the film thickness (unit: nm). In addition, the numbers in parentheses expressed as percentages indicate the ratio (mass %) of the latter compound in the layer.

[0976] <Evaluation of Organic EL Devices>

[0977] The produced organic EL device was evaluated as follows.

[0978] Component life

[0979] At room temperature, the current density reaches 50mA / cm 2 A voltage was applied to the organic EL element in the manner of , and the time until the luminance reached 95% of the initial luminance (LT95 (unit: h)) was measured. The LT95 ratio (%) represents a relative value when Comparative Example 3 described later is set as 100.

[0980] Comparative Example 3

[0981] The organic EL device was prepared and evaluated in the same manner as in Example 22 except that the compound described in Table 3 was used instead of ET-4.

[0982] [Table 3]

[0983] First electron transport layer LT95(h) LT95 ratio (%) Embodiment 22 ET-4 153 132 Comparative Example 3 ET-Ref3 116 100

[0984] <Synthesis of Compounds>

[0985] (Synthesis Example 1) Synthesis of ET-1

[0986] ET-1 was synthesized by the following synthetic route.

[0987] [Chemistry 141]

[0988]

[0989] 4-Chloro-2,6-diphenylpyrimidine (4.50 g), 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.87 g), and (Amphos) 2 PdCl 2 (0.30 g) was added to a beaker, and after replacing the atmosphere in the beaker with argon, 1,4-dioxane (169 mL) and 2M sodium carbonate aqueous solution (21.1 mL) were added, and heated and stirred under reflux conditions for 6.5 hours. After the reaction solution was cooled, dichloromethane was added and the resulting solution was filtered through silica gel. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with hexane to obtain ET-1 as a white solid (7.45 g, yield 93%).

[0990] As a result of mass spectrometry, the molecular weight was 474.61, and m / e was 475, so the white solid was identified as the target substance.

[0991] (Synthesis Example 2) Synthesis of ET-2

[0992] ET-2 was synthesized by the following synthetic route.

[0993] [Chemistry 142]

[0994]

[0995] 4-([1,1'-biphenyl]-3-yl)-6-chloro-2-phenylpyrimidine (4.50 g), 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.87 g), Pd 2 (dba) 3 (0.24 g), and SPhos (0.43 g) were added to a beaker, and after replacing the atmosphere in the beaker with argon, 1,4-dioxane (131 mL) and 2M sodium carbonate aqueous solution (16.4 mL) were added, and heated and stirred for 6 hours under reflux conditions. After the reaction solution was cooled, dichloromethane was added and the resulting solution was filtered through silica gel. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with hexane to obtain ET-2 as a white solid (5.66 g, yield 78%).

[0996] As a result of mass spectrometry, the molecular weight was 550.71, and m / e was 551, so the white solid was identified as the target substance.

[0997] (Synthesis Example 3) Synthesis of ET-3

[0998] ET-3 was synthesized by the following synthetic route.

[0999] [Chemistry 143]

[1000]

[1001] 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (4.07 g), 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.43 g), Pd 2 (dba) 3 (0.18 g), and Amphos (0.21 g) were added to a beaker, the atmosphere in the beaker was replaced with argon, 1,4-dioxane (67 mL) and 2M sodium carbonate aqueous solution (15.0 mL) were added, and the mixture was heated and stirred under reflux for 6 hours. After the reaction solution was cooled, H 2 O, and extracted with dichloromethane. The solvent was distilled off, and the obtained crude product was purified by silica gel chromatography and recrystallization using toluene / hexane to obtain ET-3 as a white solid (2.90 g, yield 53%).

[1002] As a result of mass spectrometry, the molecular weight was 550.71, and m / e was 551, so the white solid was identified as the target substance.

[1003] (Synthesis Example 4) Synthesis of ET-4

[1004] ET-4 was synthesized by the following synthetic route.

[1005] [Chemistry 144]

[1006]

[1007] 4,6-dichloro-2-phenylpyrimidine (17.84 g), 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14.68 g) and PdCl 2 (dppf)CH 2 Cl 2(1.30g) was added to a beaker, and after replacing the atmosphere in the beaker with argon, toluene (317mL), DME (79mL) and 2M sodium carbonate aqueous solution (59.5mL) were added, and heated and stirred for 6.5 hours under reflux conditions. The reaction solution was cooled and filtered through silica gel. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with hexane to obtain 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine as a white solid (13.37g, yield 76%).

[1008] [Chemistry 145]

[1009]

[1010] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.30 g), 2-(4-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.23 g) and (Amphos) 2 PdCl 2 (0.28g) was added to a beaker, and after replacing the atmosphere in the beaker with argon, 1,4-dioxane (99mL) and 2M sodium carbonate aqueous solution (12.4mL) were added, and heated and stirred under reflux conditions for 4 hours. After the reaction solution was cooled, MeOH was added and the precipitated solid was filtered out. The obtained crude product was purified by silica gel chromatography and washed with hexane to obtain ET-4 as a white solid (4.90g, yield 77%).

[1011] As a result of mass spectrometry, the molecular weight was 640.79, and m / e was 641, so the white solid was identified as the target substance.

[1012] (Synthesis Example 5) Synthesis of ET-5

[1013] ET-5 was synthesized by the following synthetic route.

[1014] [Chemistry 146]

[1015]

[1016] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.30 g), (3-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid (3.72 g) and (Amphos) 2 PdCl 2(0.28g) was added to a beaker, and after replacing the atmosphere in the beaker with argon, 1,4-dioxane (99mL) and 2M sodium carbonate aqueous solution (12.4mL) were added, and heated and stirred for 4 hours under reflux conditions. After the reaction solution was cooled, MeOH was added and the precipitated solid was filtered out. The obtained crude product was purified by silica gel chromatography and washed with hexane to obtain ET-5 as a white solid (2.84g, yield 45%).

[1017] As a result of mass spectrometry, the molecular weight was 640.79, and m / e was 641, so the white solid was identified as the target substance.

[1018] (Synthesis Example 6) Synthesis of ET-6

[1019] ET-6 was synthesized by the following synthetic route.

[1020] [Chemistry 147]

[1021]

[1022] 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)pyrimidine (5.40 g), 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene (3.78 g) and (Amphos) 2 PdCl 2 (0.32 g) was added to a beaker, and after replacing the atmosphere in the beaker with argon, 1,4-dioxane (111 mL) and 2M sodium carbonate aqueous solution (13.9 mL) were added, and heated and stirred at 74°C for 22 hours. After cooling the reaction solution, it was filtered through silica gel. The solvent was distilled off, and the obtained crude product was purified by silica gel chromatography, thereby obtaining ET-6 as a white solid (4.81 g, yield 71%).

[1023] As a result of mass spectrometry, the molecular weight was 600.77, and m / e was 601, and the white solid was identified as the target substance.

[1024] (Synthesis Example 7) Synthesis of ET-7

[1025] ET-7 was synthesized by the following synthetic route.

[1026] [Chemistry 148]

[1027]

[1028] 4-([1,1'-biphenyl]-3-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)pyrimidine (7.00 g), 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene (4.84 g), Pd 2 (dba) 3 (0.23g) and SPhos (0.41g) were added to a beaker, and after replacing the atmosphere in the beaker with argon, 1,4-dioxane (125mL) and 2M sodium carbonate aqueous solution (15.6mL) were added, and heated and stirred for 7 hours under reflux conditions. After cooling the reaction solution, it was filtered through silica gel. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with hexane to obtain ET-7 as a white solid (7.46g, yield 88%).

[1029] As a result of mass spectrometry, the molecular weight was 676.86, and m / e was 677, and the white solid was identified as the target substance.

[1030] (Synthesis Example 8) Synthesis of ET-8

[1031] ET-8 was synthesized by the following synthetic route.

[1032] [Chemistry 149]

[1033]

[1034] 4-([1,1'-biphenyl]-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (5.00 g), 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.79 g), Pd 2 (dba) 3 (0.20 g) and SPhos (0.35 g) were added to a beaker, and after replacing the atmosphere in the beaker with argon, 1,4-dioxane (108 mL) and 2M sodium carbonate aqueous solution (13.5 mL) were added, and heated and stirred under reflux conditions for 7 hours. The reaction solution was filtered through silica gel, the solvent was distilled off, and the obtained crude product was purified by silica gel chromatography and washed with hexane to obtain ET-8 as a white solid (5.78 g, yield 85%).

[1035] As a result of mass spectrometry, the white solid was identified as the target substance with a molecular weight of 626.80 and m / e=627.

[1036] (Synthesis Example 9) Synthesis of ET-9

[1037] ET-9 was synthesized by the following synthetic route.

[1038] [Chemistry 150]

[1039]

[1040] 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)pyrimidine (4.84 g), 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene (3.23 g), Pd 2 (dba) 3 (0.18 g) and SPhos (0.33 g) were added to a beaker, replaced with argon, and then 1,4-dioxane (67 mL) and 2M sodium carbonate aqueous solution (25 mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water and dichloromethane were added to extract the oil phase. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography, and ET-9 was obtained as a light yellow solid (3.43 g, yield 57%) by recrystallization using toluene.

[1041] As a result of mass spectrometry, the molecular weight was 600.76, and m / e was 601, so the product was identified as the target substance.

[1042] (Synthesis Example 10) Synthesis of ET-10

[1043] ET-10 was synthesized by the following synthetic route.

[1044] [Chemistry 151]

[1045]

[1046] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (9.80 g), 2-(9,9-dimethyl-9H-fluoren-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.70 g) and Pd(PPh 3 ) 4 (0.52g) was added to a beaker, replaced with argon, and then DME (186mL) and 2M sodium carbonate aqueous solution (22.6mL) were added, and heated and stirred under reflux conditions for 19 hours. After the reaction solution was cooled, toluene was added for liquid separation, and the oil phase was recovered. After distilling off the solvent, MeOH was added and the precipitated solid was filtered out. The obtained crude product was purified by silica gel chromatography and washed with a mixed solvent of heptane and xylene, thereby obtaining ET-10 as a white solid (7.86g, yield 58%).

[1047] As a result of mass spectrometry, the molecular weight was 590.77, and m / e was 591, so the product was identified as the target substance.

[1048] (Synthesis Example 11) Synthesis of ET-11

[1049] ET-11 was synthesized by the following synthetic route.

[1050] [Chemistry 152]

[1051]

[1052] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.33 g), (3-(naphthalen-1-yl)phenyl)boronic acid (2.60 g) and (Amphos) 2 PdCl 2 (0.28g) was added to a beaker, replaced with argon, and then 1,4-dioxane (67mL) and 2M sodium carbonate aqueous solution (12.5mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water and dichloromethane were added, and the liquid was separated to extract the oil phase. The solvent was distilled off, and the obtained crude product was purified by silica gel chromatography, thereby obtaining ET-11 as a light yellow solid (4.14g, yield 69%).

[1053] As a result of mass spectrometry, the molecular weight was 600.76, and m / e was 601, so the product was identified as the target substance.

[1054] (Synthesis Example 12) Synthesis of ET-12

[1055] ET-12 was synthesized by the following synthetic route.

[1056] [Chemistry 153]

[1057]

[1058] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.33 g), (3-(phenanthrene-9-yl)phenyl)boronic acid (3.13 g) and (Amphos) 2 PdCl 2 (0.28g) was added to a beaker, replaced with argon, and then 1,4-dioxane (67mL) and 2M sodium carbonate aqueous solution (12.5mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water and dichloromethane were added, and the liquid was separated to extract the oil phase. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography to obtain ET-12 as a light yellow solid (3.38g, yield 52%).

[1059] As a result of mass spectrometry, the molecular weight was 650.82, and m / e was 651, so the product was identified as the target substance.

[1060] (Synthesis Example 13) Synthesis of ET-13

[1061] ET-13 was synthesized by the following synthetic route.

[1062] [Chemistry 154]

[1063]

[1064] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.33 g), (3-(phenanthrene-1-yl)phenyl)boronic acid (3.13 g) and (Amphos) 2 PdCl 2 (0.28g) was added to a beaker, replaced with argon, and then 1,4-dioxane (67mL) and 2M sodium carbonate aqueous solution (12.5mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water and dichloromethane were added, and the liquid was separated to extract the oil phase. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography to obtain ET-13 as a light yellow solid (3.78g, yield 58%).

[1065] As a result of mass spectrometry, the molecular weight was 650.82, and m / e was 651, so the product was identified as the target substance.

[1066] (Synthesis Example 14) Synthesis of ET-14

[1067] ET-14 was synthesized by the following synthetic route.

[1068] [Chemistry 155]

[1069]

[1070] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.33 g), [1,1':3',1"-terphenyl]-5'-boronic acid (2.88 g) and (Amphos) 2 PdCl 2 (0.28g) was added to a beaker, replaced with argon, and then 1,4-dioxane (67mL) and 2M sodium carbonate aqueous solution (12.5mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water and dichloromethane were added, and the liquid was separated to extract the oil phase. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography, and ET-14 was obtained as a white solid (4.38g, yield 70%) by recrystallization using toluene.

[1071] As a result of mass spectrometry, the molecular weight was 626.80, and m / e was 627, so the product was identified as the target substance.

[1072] (Synthesis Example 15) Synthesis of ET-15

[1073] ET-15 was synthesized by the following synthetic route.

[1074] [Chemistry 156]

[1075]

[1076] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.08 g), 4,4,5,5-tetramethyl-2-(phenanthrene-3-yl)-1,3,2-dioxaborolane (3.44 g) and (Amphos) 2 PdCl 2 (0.27g) was added to a beaker, replaced with argon, and then 1,4-dioxane (94mL) and 2M sodium carbonate aqueous solution (14.1mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water and dichloromethane were added, and the liquid was separated to extract the oil phase. The solvent was distilled off, and the obtained crude product was purified by silica gel chromatography, and ET-15 was obtained as a light yellow solid (2.55g, yield 47%) by recrystallization using toluene.

[1077] As a result of mass spectrometry, the molecular weight was 574.72, and m / e was 575, so the product was identified as the target substance.

[1078] (Synthesis Example 16) Synthesis of ET-16

[1079] ET-16 was synthesized by the following synthetic route.

[1080] [Chemistry 157]

[1081]

[1082] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.33 g), dibenzo[b,d]furan-2-ylboronic acid (2.22 g) and (Amphos) 2 PdCl 2 (0.28g) was added to a beaker, replaced with argon, and then 1,4-dioxane (67mL) and 2M sodium carbonate aqueous solution (12.5mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water was added and the precipitated solid was filtered out. The obtained crude product was purified by silica gel chromatography to obtain ET-16 as a white solid (3.62g, yield 64%).

[1083] As a result of mass spectrometry, the molecular weight was 564.68, and m / e was 565, so the product was identified as the target substance.

[1084] (Synthesis Example 17) Synthesis of ET-17

[1085] ET-17 was synthesized by the following synthetic route.

[1086] [Chemistry 158]

[1087]

[1088] 4-Chloro-6-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-2-phenylpyrimidine (4.33 g), dibenzo[b,d]thiophen-2-ylboronic acid (2.40 g) and (Amphos) 2 PdCl 2 (0.28g) was added to a beaker, replaced with argon, and then 1,4-dioxane (67mL) and 2M sodium carbonate aqueous solution (12.5mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, water was added and the precipitated solid was filtered out. The obtained crude product was purified by silica gel chromatography and ET-17 was obtained as a white solid (4.13g, yield 71%) by recrystallization using xylene.

[1089] As a result of mass spectrometry, the molecular weight was 580.74, and m / e was 581, so the product was identified as the target substance.

[1090] (Synthesis Example 18) Synthesis of ET-18

[1091] ET-18 was synthesized by the following synthetic route.

[1092] [Chemistry 159]

[1093]

[1094] 4-Chloro-2,6-di(phenyl-2,3,4,5,6-d5)pyrimidine (3.50 g), 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.15 g) and (Amphos) 2 PdCl 2(0.22g) was added to a beaker, replaced with argon, and then 1,4-dioxane (126mL) and 2M sodium carbonate aqueous solution (15.8mL) were added, and heated and stirred under reflux conditions for 7 hours. After the reaction solution was cooled, dichloromethane was added, and the resulting solution was filtered through silica gel. The solvent was distilled off, and the resulting crude product was purified by silica gel chromatography and washed with hexane to obtain ET-18 as a white solid (5.03g, yield 82%).

[1095] As a result of mass spectrometry, the molecular weight was 483.66, and m / e was 484, so the product was identified as the target substance.

[1096] (Synthesis Example 19) Synthesis of ET-19

[1097] ET-19 was synthesized by the following synthetic route.

[1098] [Chemistry 160]

[1099]

[1100] 4-(4-bromo-1-naphthyl)-2-phenyl-6-(phenyl-2,3,4,5,6-d5)pyrimidine (3.00 g), 2-(7,7-dimethyl-7H-benzo[c]fluoren-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.64 g) and (Amphos) 2 PdCl 2 (0.19 g) was added to a beaker, replaced with argon, and then 1,4-dioxane (68 mL) and 2M sodium carbonate aqueous solution (8.5 mL) were added, and heated and stirred at 74°C for 7 hours. The reaction solution was cooled and filtered through silica gel. The solvent was distilled off, and the obtained crude product was purified by silica gel chromatography to obtain ET-19 as a white solid (2.59 g, yield 63%).

[1101] As a result of mass spectrometry, the molecular weight was 605.79, and m / e was 606, so the product was identified as the target substance.

[1102] Several embodiments and / or examples of the present invention are described in detail above, but it is easy for those skilled in the art to make many changes to these illustrative embodiments and / or examples without actually departing from the novel teachings and effects of the present invention. Therefore, these many changes are also included in the scope of the present invention.

[1103] The contents of the documents described in this specification and the applications serving as the basis for the Paris Convention priority claim of the present application are incorporated herein by reference in their entirety.

Claims

1. A compound represented by the following formula (1), [Chemistry 161] In formula (1), X1 and X2 are each independently N or CH, and either X1 or X2 is N; Ar1 and Ar2 are each independently: a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; L1 to L3 are each independently: single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; n1 is an integer from 0 to 4. When n1 is 0, (L1) n1 is a single bond; when there are multiple L1s, the multiple L1s may be the same or different; n2 is an integer from 0 to 4. When n2 is 0, (L2) n2 is a single bond; when there are multiple L2, the multiple L2 may be the same or different; n3 is an integer from 0 to 4. When n3 is 0, (L3) n3 is a single bond; when there are multiple L3, the multiple L3 may be the same or different; R 11 ~R 19 Each independently is a hydrogen atom or a substituent R; 11 ~R 19 The adjacent groups of two or more are not bonded to each other; R 21 and R 22 Bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring; The R that does not form a substituted or unsubstituted saturated or unsaturated ring 21 and R 22 Each independently is: Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; The substituent R is selected from: 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 carbon atoms, -Si(R 901 )(R 902 )(R 903 )、 -O-(R 904 )、 -S-(R 905 )、 -N(R 906 )(R 907 )、 Halogen atoms, cyano, nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 Each independently is: Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 Each can be the same or different; When there are two or more substituents R, the two or more substituents R may be the same or different.

2. The compound according to claim 1, wherein The compound represented by the formula (1) is a compound represented by the following formula (11), [Chemistry 162] In formula (11), X1, X2, Ar1, Ar2, L1, L2, n1, n2, R 11 ~R 19 , R 21 and R 22 As defined in formula (1).

3. The compound according to claim 2, wherein R 21 and R 22 A substituted or unsubstituted saturated or unsaturated ring is not formed.

4. The compound according to claim 2 or 3, wherein R 21 and R 22 Each is independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

5. The compound according to any one of claims 2 to 4, wherein R 21 and R 22 It is methyl.

6. The compound according to any one of claims 2 to 5, wherein X1 is N, and X2 is CH.

7. The compound according to any one of claims 2 to 6, wherein The compound represented by the formula (11) is a compound represented by any one of the following formulas (111) to (113); [Chemistry 163] [Chemistry 164] In formula (111), L1, L2, n1, n2 and R 11 ~R 19 As defined in formula (1); R 111 ~R 120 Each independently is a hydrogen atom or a substituent R; 111 ~R 120 The adjacent groups of two or more are not bonded to each other; In formula (112), L1, L2, n1, n2 and R 11 ~R 19 As defined in formula (1); Y1 is N(R 129 )、C(R 130a )(R 130b ), O or S; R 121 ~R 129 Any of represents a bond to L2; R does not represent a bond with L2 121 ~R 129 Each independently represents a hydrogen atom or a substituent R; R which does not represent a bond with L2 121 ~R 129 The adjacent groups of two or more are not bonded to each other; R 130a and R 130b Bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring; The R that does not form a substituted or unsubstituted saturated or unsaturated ring 130a and R 130b Each is independently a hydrogen atom or a substituent R; R 131 ~R 135 Each independently is a hydrogen atom or a substituent R; 131 ~R 135 The adjacent groups of two or more are not bonded to each other; In formula (113), L1, L2, n1, n2 and R 11 ~R 19 As defined in formula (1); R 141 ~R 150 Any of represents a bond to L2; R does not represent a bond with L2 141 ~R 150 Each independently represents a hydrogen atom or a substituent R; R which does not represent a bond with L2 141 ~R 150 The adjacent groups of two or more are not bonded to each other; R 151 ~R 155 Each independently is a hydrogen atom or a substituent R; 151 ~R 155 The adjacent groups of two or more are not bonded to each other; The substituent R is as defined above for the formula (1).

8. The compound according to any one of claims 2 to 5, wherein X1 is CH, and X2 is N.

9. The compound according to claim 1, wherein The compound represented by the formula (1) is a compound represented by the following formula (21), [Chemistry 165] In formula (21), X1, X2, Ar1, Ar2, L1, L2, n1, n2, R 11 ~R 19 , R 21 and R 22 As defined in formula (1); L 21 for: a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; n21 is an integer from 1 to 4; L 21 When there are multiple L 21 Each may be the same or different.

10. The compound according to claim 9, wherein R 21 and R 22 A substituted or unsubstituted saturated or unsaturated ring is not formed.

11. The compound according to claim 9 or 10, wherein R 21 and R 22 Each is independently a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

12. The compound according to any one of claims 9 to 11, wherein R 21 and R 22 It is methyl.

13. The compound according to any one of claims 9 to 12, wherein L 21 It is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

14. The compound according to any one of claims 9 to 13, wherein L 21 for: Substituted or unsubstituted phenylene, or A substituted or unsubstituted naphthylene group.

15. The compound according to any one of claims 9 to 14, wherein X1 is N, and X2 is CH.

16. The compound according to any one of claims 9 to 15, wherein The compound represented by the formula (21) is a compound represented by the following formula (211) or formula (212), [Chemistry 166] In formula (211), Ar1, Ar2, L1, L2, n1, n2 and R 11 ~R 19 As defined in formula (1); R 211 ~R 214 Each independently is a hydrogen atom or a substituent R; 211 ~R 214 The adjacent groups of two or more are not bonded to each other; In formula (212), Ar1, Ar2, L1, L2, n1, n2 and R 11 ~R 19 As defined in formula (1); R 221 ~R 226 Each independently is a hydrogen atom or a substituent R; 221 ~R 226 The adjacent groups of two or more are not bonded to each other; The substituent R is as defined above for the formula (1).

17. The compound according to any one of claims 9 to 14, wherein X1 is CH, and X2 is N.

18. The compound according to claim 17, wherein The compound represented by the formula (21) is a compound represented by the following formula (221) or formula (222), [Chemistry 167] In formula (221), Ar1, Ar2, L1, L2, n1, n2 and R 11 ~R 19 As defined in formula (1); R 211 ~R 214 Each independently is a hydrogen atom or a substituent R; 211 ~R 214 The adjacent groups of two or more are not bonded to each other; In formula (222), Ar1, Ar2, L1, L2, n1, n2 and R 11 ~R 19 As defined in formula (1); R 221 ~R 226 Each independently is a hydrogen atom or a substituent R; 221 ~R 226 The adjacent groups of two or more are not bonded to each other; The substituent R is as defined above for the formula (1).

19. The compound according to any one of claims 9 to 18, wherein Ar1 and Ar2 are each independently: a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or A substituted or unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

20. The compound according to any one of claims 9 to 19, wherein Ar1 and Ar2 are each independently: Substituted or unsubstituted phenyl, or Substituted or unsubstituted naphthyl.

21. The compound according to any one of claims 1 to 20, wherein L1 and L2 are each independently: single bond, Substituted or unsubstituted phenylene, or A substituted or unsubstituted naphthylene group.

22. The compound according to any one of claims 1 to 21, wherein R 11 ~R 19 A hydrogen atom.

23. The compound according to any one of claims 1 to 22, wherein The substituents in the case of "substituted or unsubstituted" and the substituent R are selected from the following groups: Alkyl groups having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and A monovalent heterocyclic group having 5 to 50 ring atoms.

24. The compound according to any one of claims 1 to 23, wherein The substituents in the case of "substituted or unsubstituted" and the substituent R are selected from the following groups: Alkyl groups having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and A monovalent heterocyclic group having 5 to 18 ring atoms. 25 . The compound according to claim 1 , which is a material for an organic electroluminescent device.

26. An organic electroluminescent element, comprising: cathode, Anode, and One or more organic layers disposed between the cathode and the anode; At least one of the organic layers contains the compound according to any one of claims 1 to 25.

27. The organic electroluminescent element according to claim 26, comprising an anode, a light-emitting layer, an electron transport region and a cathode in sequence; The electron transport region includes the compound.

28. The organic electroluminescent element according to claim 27, wherein The electron transport region has a first layer and a second layer in order from the light emitting layer side, The first layer includes the compound.

29. An electronic device comprising the organic electroluminescent element according to any one of claims 26 to 28.

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