Compound, organic electroluminescent element and electronic device using the same

Abstract

A compound represented by the following formula (1) (at least one of R1 to R8 is a deuterium atom, and at least one of Ar1 and Ar2 is a substituted or unsubstituted condensed aromatic group consisting of only four or more benzene rings bonded together).

Description

Technical Field

[0001] The present invention relates to a novel compound, an organic electroluminescent element and an electronic device using the same. Background Art

[0002] When voltage is applied to an organic electroluminescent element (hereinafter sometimes 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, respectively. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] Patent Documents 1 to 6 disclose the use of an anthracene compound having a specific structure as a host material for a light-emitting layer of an organic EL element.

[0004] Prior art literature

[0005] Patent Literature

[0006] [Patent Document 1] WO2010 / 099534

[0007] [Patent Document 2] WO2010 / 135395

[0008] [Patent Document 3] WO2011 / 028216

[0009] [Patent Document 4] WO2010 / 071362

[0010] [Patent Document 5] US20120217449

[0011] [Patent document 6] US20120326602. Summary of the invention

[0012] An object of the present invention is to provide a novel compound capable of improving (enhancing) the life of a device, and an organic electroluminescent device having an improved device life using the novel compound.

[0013] According to the present invention, the following compound, material for an organic electroluminescent device, composition, organic electroluminescent device and electronic device can be provided.

[0014] 1. A compound represented by the following formula (1).

[0015] [Chemistry 1]

[0016]

[0017] (In formula (1),

[0018] R1~R8 are independently

[0019] Hydrogen atoms,

[0020] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0021] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0022] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0023] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0024] -Si(R 901 )(R 902 )(R 903 ),

[0025] -O-(R 904 ),

[0026] -S-(R 905 ),

[0027] -N(R 906 )(R 907 ),

[0028] Halogen atoms, cyano, nitro,

[0029] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0030] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms,

[0031] R 901 ~R 907 Each independently

[0032] Hydrogen atoms,

[0033] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0034] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0035] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0036] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms,

[0037] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different.

[0038] Two or more adjacent R1 to R8 are not bonded to each other to form a ring,

[0039] wherein at least one of R1 to R8 is a deuterium atom,

[0040] L1 and L2 are independently

[0041] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0042] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[0043] m11 and m12 are each independently an integer of 0 to 4. When m11 and m12 are 0, (L1) m11 and (L2) m12 is a single bond, and when m11 or m12 is 2 or more, the two or more m11 or m12 may be the same as or different from each other.

[0044] Ar1 and Ar2 are each independently

[0045] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0046] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms,

[0047] wherein at least one of Ar1 and Ar2 is a substituted or unsubstituted fused aromatic group consisting of only 4 or more benzene rings fused together,

[0048] One or more of the hydrogen atoms possessed by one or more groups selected from L1, L2, Ar1 and Ar2 may be deuterium atoms.

[0049] 2. A material for an organic electroluminescent device, comprising the compound represented by the above formula (1).

[0050] 3. A composition comprising a compound represented by the above formula (1), wherein the content ratio of the latter is 99 mol% or less relative to the total of the compound represented by the above formula (1) and a compound having the same structure as the compound represented by the above formula (1) except that it contains only protium atoms as hydrogen atoms.

[0051] 4. An organic electroluminescent element comprising a cathode, an anode, and a light-emitting layer disposed between the cathode and the anode,

[0052] The light-emitting layer contains the compound according to any one of claims 1 to 18.

[0053] 5. An electronic device comprising the organic electroluminescent element according to 4 above.

[0054] According to the present invention, a novel compound capable of improving (enhancing) the device life and an organic electroluminescent device using the novel compound having improved device life can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0055] [ Figure 1 ] A schematic diagram of an organic electroluminescent element according to 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, a heterocyclic compound) in which atoms are bonded to form a ring structure. When the ring is substituted by 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] When a benzene ring or a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the ring.

[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, a heterocyclic compound) in which atoms are bonded to form a cyclic structure (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, 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. The hydrogen atoms bonded to the carbon atoms of the pyridine ring and the quinazoline ring and the atoms constituting the substituent are not included in the number of ring atoms.

[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. Herein, "YY" is greater than "XX", and "XX" and "YY" each mean an integer greater than 1.

[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 of the ZZ group when it is unsubstituted, and does not include the number of atoms of the substituent when it is substituted. Herein, "YY" is greater than "XX", and "XX" and "YY" each mean an integer greater than 1.

[0064] "Unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the ZZ group is not substituted by a substituent but has a hydrogen atom bonded thereto. Alternatively, "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 an AA group.

[0065] Hereinafter, the substituents described in the present specification will be described.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] Unless otherwise specified in the present specification, the number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0074] 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.

[0075] As specific examples of the "substituted or unsubstituted aryl group" described in this specification (specific example group G1), the following unsubstituted aryl groups and substituted aryl groups can be cited. (Herein, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) Hereinafter, when "aryl group" is mentioned alone, both "unsubstituted aryl group" and "substituted aryl group" are included.

[0076] "Substituted aryl" refers to the case where "unsubstituted aryl" has a substituent, and examples of "unsubstituted aryl" and "substituted aryl" mentioned below 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 a group where the "unsubstituted aryl" has a substituent further has a substituent, and a group where the "substituted aryl" further has a substituent.

[0077] Unsubstituted aryl:

[0078] Phenyl,

[0079] p-Biphenyl,

[0080] m-Biphenyl,

[0081] o-Biphenyl,

[0082] 4-terphenyl-4-yl,

[0083] 4-terphenyl-3-yl,

[0084] 4-terphenyl-2-yl,

[0085] m-terphenyl-4-yl,

[0086] m-terphenyl-3-yl,

[0087] m-terphenyl-2-yl,

[0088] o-terphenyl-4-yl,

[0089] o-terphenyl-3-yl,

[0090] o-terphenyl-2-yl,

[0091] 1-naphthyl,

[0092] 2-naphthyl,

[0093] Anthracene,

[0094] Benzanthryl,

[0095] Fiki,

[0096] Triphenylene,

[0097] Phenyl,

[0098] Pyrene

[0099] Hexyl

[0100] Benzopheneyl,

[0101] Triphenylene,

[0102] Benzotriphenylene,

[0103] Tetraphenylene,

[0104] Pentaphenyl,

[0105] Fluorene,

[0106] 9,9'-Spirobifluorenyl,

[0107] Benzofluorenyl,

[0108] Dibenzofluorenyl,

[0109] Fluoranthene group,

[0110] Benzofluoranthene,

[0111] Peryl.

[0112] Substituted aryl groups:

[0113] o-Toluyl,

[0114] m-Toluene

[0115] p-Tolyl,

[0116] p-Xylyl,

[0117] m-Xylyl,

[0118] o-Xylyl,

[0119] p-Isopropylphenyl,

[0120] m-isopropylphenyl,

[0121] o-isopropylphenyl,

[0122] 4-tert-Butylphenyl,

[0123] m-tert-butylphenyl,

[0124] o-tert-butylphenyl,

[0125] 3,4,5-Trimethylphenyl,

[0126] 9,9-dimethylfluorenyl,

[0127] 9,9-Diphenylfluorenyl,

[0128] 9,9-di(4-methylphenyl)fluorenyl,

[0129] 9,9-di(4-isopropylphenyl)fluorenyl,

[0130] 9,9-di(4-tert-butylphenyl)fluorenyl,

[0131] Cyanophenyl,

[0132] Triphenylsilylphenyl,

[0133] Trimethylsilylphenyl,

[0134] Phenyl naphthyl,

[0135] Naphthylphenyl.

[0136] 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.

[0137] The "heterocyclic group" described in the present specification may be a monocyclic group or a condensed ring group.

[0138] The "heterocyclic group" described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.

[0139] As specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (specific example group G2), the following unsubstituted heterocyclic groups and substituted heterocyclic groups can be cited. (Herein, 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".) Hereinafter, when a "heterocyclic group" is mentioned alone, both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" are included.

[0140] "Substituted heterocyclic group" refers to the case where "unsubstituted heterocyclic group" has a substituent, and examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed below can be cited. 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 also includes a group where the "unsubstituted heterocyclic group" has a substituent further has a substituent, and a group where the "substituted heterocyclic group" further has a substituent.

[0141] Unsubstituted heterocyclic group containing nitrogen atom:

[0142] Pyrrolyl,

[0143] Imidazole,

[0144] Pyrazolyl,

[0145] Triazole,

[0146] Tetrazolyl,

[0147] Oxazolyl,

[0148] Isoxazolyl,

[0149] Oxadiazolyl,

[0150] Thiazolyl,

[0151] Isothiazolyl,

[0152] Thiadiazole,

[0153] Pyridyl,

[0154] Pyridazine

[0155] Pyrimidine,

[0156] Pyrazinyl,

[0157] Triazine,

[0158] Indolyl,

[0159] Isoindolyl,

[0160] Indolizinyl,

[0161] Quinolizinyl,

[0162] Quinoline,

[0163] Isoquinolinyl,

[0164] Cinnoline,

[0165] Phthalocyanine

[0166] Quinazoline,

[0167] Quinoxaline,

[0168] Benzimidazolyl,

[0169] Indazolyl,

[0170] Phenanthroline,

[0171] Phenanthridinyl,

[0172] Acridinium,

[0173] Phenolic acid,

[0174] Carbazolyl,

[0175] Benzocarbazolyl,

[0176] Morpholino,

[0177] Phenoxazine,

[0178] Phenothiazine,

[0179] Azacarbazolyl,

[0180] Diazacarbazolyl.

[0181] Unsubstituted heterocyclic group containing oxygen atom:

[0182] Furanyl,

[0183] Oxazolyl,

[0184] Isoxazolyl,

[0185] Oxadiazolyl,

[0186] Xanthyl,

[0187] Benzofuranyl,

[0188] Isobenzofuranyl,

[0189] Dibenzofuranyl,

[0190] Naphthobenzofuranyl,

[0191] Benzoxazolyl,

[0192] Benzisoxazolyl,

[0193] Phenoxazine,

[0194] Morpholino,

[0195] dinaphthofuranyl,

[0196] Azadibenzofuranyl,

[0197] Diazadibenzofuranyl,

[0198] Azanaphthobenzofuranyl,

[0199] naphthyridinylbenzofuranyl.

[0200] Unsubstituted heterocyclic group containing a sulfur atom:

[0201] Thienyl,

[0202] Thiazolyl,

[0203] Isothiazolyl,

[0204] Thiadiazole,

[0205] Benzothiphenyl,

[0206] Isobenzothiophene,

[0207] Dibenzothiophene,

[0208] Naphthobenzothiophene,

[0209] Benzothiazolyl,

[0210] Benzisothiazolyl,

[0211] Phenothiazine,

[0212] Dinaphthothienyl,

[0213] Azadibenzothiophene,

[0214] Diazadibenzothiophene,

[0215] Azanaphthobenzothiophene,

[0216] Diazinobenzothiophenyl.

[0217] Substituted heterocyclic groups containing nitrogen atoms:

[0218] (9-phenyl)carbazolyl,

[0219] (9-Biphenyl)carbazolyl,

[0220] (9-phenyl)phenylcarbazolyl,

[0221] (9-naphthyl)carbazolyl,

[0222] Diphenylcarbazole-9-yl,

[0223] Phenylcarbazol-9-yl,

[0224] Methylbenzimidazolyl,

[0225] Ethylbenzimidazolyl,

[0226] Phenyl triazine,

[0227] Biphenyl triazine,

[0228] Diphenyltriazine,

[0229] Phenylquinazolinyl,

[0230] Biphenylquinazolinyl.

[0231] Substituted heterocyclic groups containing oxygen atoms:

[0232] Phenyldibenzofuranyl,

[0233] Methyldibenzofuranyl,

[0234] tert-Butyldibenzofuranyl,

[0235] A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0236] Substituted heterocyclic groups containing a sulfur atom:

[0237] Phenyldibenzothiophene,

[0238] Methyldibenzothiophene,

[0239] tert-Butyldibenzothienyl,

[0240] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0241] A monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of the following unsubstituted heterocyclic ring containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom, and a group having a substituent which is derived by removing one hydrogen atom bonded to a ring-forming atom of the following unsubstituted heterocyclic ring:

[0242] [Chemistry 2]

[0243]

[0244] In formulas (XY-1) to (XY-18), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH, or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0245] The heterocyclic rings represented by the above formulae (XY-1) to (XY-18) have a bond at an arbitrary position to form a monovalent heterocyclic group.

[0246] The monovalent group derived from the unsubstituted heterocyclic ring represented by the above formulae (XY-1) to (XY-18) having a substituent means that the hydrogen atom bonded to the carbon atom constituting the skeleton in these formulae is replaced by a substituent, or XA , Y A It is NH or CH2, and the hydrogen atom in these NH or CH2 is replaced by a substituent.

[0247] As specific examples of the "substituted or unsubstituted alkyl group" described in this specification (specific example group G3), the following unsubstituted alkyl groups and substituted alkyl groups can be cited. (Herein, unsubstituted alkyl groups refer to the case where "substituted or unsubstituted alkyl groups" are "unsubstituted alkyl groups", and substituted alkyl groups refer to the case where "substituted or unsubstituted alkyl groups" are "substituted alkyl groups".) Hereinafter, when "alkyl groups" are mentioned alone, both "unsubstituted alkyl groups" and "substituted alkyl groups" are included.

[0248] "Substituted alkyl" refers to the case where "unsubstituted alkyl" has a substituent, and examples of "unsubstituted alkyl" and "substituted alkyl" listed below can be cited. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" described in this specification also includes a group in which the "unsubstituted alkyl" has a substituent and further has a substituent, and a group in which the "substituted alkyl" further has a substituent.

[0249] Unsubstituted alkyl:

[0250] methyl,

[0251] Ethyl,

[0252] n-propyl,

[0253] Isopropyl,

[0254] n-Butyl,

[0255] Isobutyl,

[0256] sec-butyl,

[0257] Tert-butyl.

[0258] Substituted alkyl:

[0259] Heptafluoropropyl (including isomers),

[0260] Pentafluoroethyl,

[0261] 2,2,2-Trifluoroethyl,

[0262] Trifluoromethyl.

[0263] As specific examples of "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl and substituted alkenyl can be cited. (Herein, 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".) Hereinafter, when "alkenyl" is mentioned alone, both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0264] "Substituted alkenyl" refers to the case where "unsubstituted alkenyl" has a substituent, and examples of "unsubstituted alkenyl" and "substituted alkenyl" mentioned below can be cited. It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" described in this specification also includes a group in which the "unsubstituted alkenyl" has a substituent further has a substituent, and a group in which the "substituted alkenyl" further has a substituent.

[0265] Unsubstituted alkenyl and substituted alkenyl:

[0266] Vinyl,

[0267] Allyl,

[0268] 1-Butenyl,

[0269] 2-Butenyl,

[0270] 3-Butenyl,

[0271] 1,3-Butadienyl,

[0272] 1-Methylvinyl,

[0273] 1-methylallyl,

[0274] 1,1-dimethylallyl,

[0275] 2-methylallyl,

[0276] 1,2-Dimethylallyl.

[0277] As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl groups can be cited. (Herein, 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.

[0278] The "substituted alkynyl group" is a case where the "unsubstituted alkynyl group" has a substituent, and examples thereof include the following "unsubstituted alkynyl group" having a substituent.

[0279] Unsubstituted alkynyl:

[0280] Ethynyl.

[0281] As specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6), the following unsubstituted cycloalkyl and substituted cycloalkyl can be cited. (Herein, 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".) Hereinafter, when "cycloalkyl" is mentioned alone, both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0282] "Substituted cycloalkyl" refers to the case where "unsubstituted cycloalkyl" has a substituent, and examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" mentioned below can be cited. It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and "substituted cycloalkyl" described in this specification also includes "unsubstituted cycloalkyl" and "substituted cycloalkyl" groups further having a substituent, "substituted cycloalkyl" and "substituted cycloalkyl" groups further having a substituent, etc.

[0283] Unsubstituted aliphatic cyclic groups:

[0284] Cyclopropyl,

[0285] Cyclobutyl,

[0286] Cyclopentyl,

[0287] Cyclohexyl,

[0288] 1-adamantyl,

[0289] 2-adamantyl,

[0290] 1-Norbornyl,

[0291] 2-Norbornyl.

[0292] Substituted cycloalkyl:

[0293] 4-Methylcyclohexyl.

[0294] As described in this specification, -Si(R 901 )(R 902 )(R 903 Specific examples of the group represented by (specific example group G7) include:

[0295] -Si(G1)(G1)(G1),

[0296] -Si(G1)(G2)(G2),

[0297] -Si(G1)(G1)(G2),

[0298] -Si(G2)(G2)(G2),

[0299] -Si(G3)(G3)(G3)、

[0300] -Si(G5)(G5)(G5)、

[0301] -Si(G6)(G6)(G6).

[0302] In this article,

[0303] G1 is the "aryl group" described in the specific example group G1.

[0304] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0305] G3 is the "alkyl group" described in the specific example group G3.

[0306] G5 is the "alkynyl group" described in the specific example group G5.

[0307] G6 is the "cycloalkyl group" described in the specific example group G6.

[0308] As described in this specification, -O-(R 904 Specific examples of the group represented by (specific example group G8) include:

[0309] -O (G1),

[0310] -O (G2),

[0311] -O (G3),

[0312] -O (G6).

[0313] In this article,

[0314] G1 is the "aryl group" described in the specific example group G1.

[0315] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0316] G3 is the "alkyl group" described in the specific example group G3.

[0317] G6 is the "cycloalkyl group" described in the specific example group G6.

[0318] As described in this specification, -S-(R 905 Specific examples of the group represented by (specific example group G9) include:

[0319] -S (G1),

[0320] -S (G2),

[0321] -S (G3),

[0322] -S(G6).

[0323] In this article,

[0324] G1 is the "aryl group" described in the specific example group G1.

[0325] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0326] G3 is the "alkyl group" described in the specific example group G3.

[0327] G6 is the "cycloalkyl group" described in the specific example group G6.

[0328] As described in this specification, -N (R 906 )(R 907 Specific examples of the group represented by (specific example group G10) include:

[0329] -N (G1) (G1),

[0330] -N (G2) (G2),

[0331] -N (G1) (G2)

[0332] -N (G3) (G3),

[0333] -N(G6)(G6).

[0334] In this article,

[0335] G1 is the "aryl group" described in the specific example group G1.

[0336] G2 is a "heterocyclic group" described in Specific Example Group G2.

[0337] G3 is the "alkyl group" described in the specific example group G3.

[0338] G6 is the "cycloalkyl group" described in the specific example group G6.

[0339] 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, an iodine atom, and the like.

[0340] A specific example of the "alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is an "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.

[0341] A specific example of "alkylthio" described in the present specification is a group represented by -S(G3), wherein G3 is an "alkyl" described in the specific example group G3. Unless otherwise described in the present specification, the number of carbon atoms in the "unsubstituted alkylthio" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0342] Specific examples of "aryloxy" described in the present specification are groups represented by -O(G1), where G1 is the "aryl" described in the specific example group G1. Unless otherwise described in the present specification, the number of ring carbon atoms of the "unsubstituted aryloxy" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0343] Specific examples of "arylthio" described in the present specification are groups represented by -S(G1), where G1 is the "aryl" described in Specific Example Group G1. Unless otherwise described in the present specification, the number of ring carbon atoms of the "unsubstituted arylthio" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0344] Specific examples of "aralkyl" described in this specification are groups represented by -(G3)-(G1), where G3 is an "alkyl" described in the specific example group G3, and G1 is an "aryl" described in the specific example group G1. Therefore, "aralkyl" is an embodiment of "substituted alkyl" substituted with "aryl". Unless otherwise described in this specification, "unsubstituted alkyl" substituted with "unsubstituted aryl", i.e., "unsubstituted aralkyl", has 7 to 50 carbon atoms, preferably 7 to 30, and more preferably 7 to 18 carbon atoms.

[0345] Specific examples of the "aralkyl" 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.

[0346] 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, chrysene, triphenylene, fluorenyl, 9,9'-spirobifluorenyl, 9,9-diphenylfluorenyl, and the like.

[0347] Unless otherwise described in the present specification, 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, 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 naphthiobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (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 phenylcarbazyl, (9-phenyl)phenylcarbazyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl, phenyldibenzothienyl, indolecarbazyl, pyrazinyl, pyridazinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, pyrrolo[3,2,1-jk]carbazole yl, furyl, benzofuranyl, thienyl, benzothiophenyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, thiadiazolyl, isoxazolyl, benzisoxazolyl, pyrrolidinyl, piperidinyl, piperazinyl, imidazolidinyl, indole [3,2,1-jk] carbazolyl, dibenzothiophenyl, and the like.

[0348] Unless otherwise described in the present specification, the dibenzofuranyl group and dibenzothienyl group are specifically any of the following groups.

[0349] [Chemistry 3]

[0350]

[0351] In formula (XY-76) to (XY-79), X B is an oxygen atom or a sulfur atom.

[0352] 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.

[0353] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification refers to a group obtained by changing the above-mentioned "aryl group" to a divalent group. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include groups obtained by changing the "aryl group" described in specific example group G1 to a divalent group. That is, specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include groups obtained by removing one hydrogen atom bonded to a ring carbon of the "aryl group" described in specific example group G1.

[0354] As specific examples of the "substituted or unsubstituted divalent heterocyclic group" described in the present specification (Specific Example Group G13), there can be mentioned a group obtained by changing the "heterocyclic group" described in Specific Example Group G2 to a divalent group. That is, as specific examples of the "substituted or unsubstituted divalent heterocyclic group" (Specific Example Group G13), there can be mentioned a group obtained by removing one hydrogen atom bonded to a ring-forming atom of the "heterocyclic group" described in Specific Example Group G2.

[0355] As specific examples of the "substituted or unsubstituted alkylene group" described in the present specification (specific example group G14), there can be mentioned a group obtained by changing the "alkyl group" described in specific example group G3 to a divalent group. That is, as specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14), there can be mentioned a group obtained by removing one hydrogen bonded to the carbon forming the alkane structure of the "alkyl group" described in specific example group G3.

[0356] Unless otherwise described in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any of the following groups.

[0357] [Chemistry 4]

[0358]

[0359] In formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R 908 As a substituent.

[0360] m901 is an integer of 0 to 4. When m901 is 2 or more, multiple R 908 They may be the same as or different from each other.

[0361] [Chemistry 5]

[0362]

[0363] In formula (XY-30) to (XY-40), R 909 Each R is independently a hydrogen atom or a substituent. 909 They may be bonded to each other via a single bond to form a ring.

[0364] [Chemistry 6]

[0365]

[0366] In formula (XY-41) to (XY-46), R 910 As a substituent.

[0367] m902 is an integer from 0 to 6. When m902 is 2 or more, a plurality of R 910 They may be the same as or different from each other.

[0368] Unless otherwise described in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any of the following groups.

[0369] [Chemistry 7]

[0370]

[0371] In formula (XY-50)~(XY-60), R 911 is a hydrogen atom or a substituent.

[0372] [Chemistry 8]

[0373]

[0374] In the above formulas (XY-65) to (XY-75), X B is an oxygen atom or a sulfur atom.

[0375] In this specification, the case of “two or more adjacent groups bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring” is described by taking the case of an anthracene compound represented by the following formula (XY-80) whose parent skeleton is an anthracene ring as an example.

[0376] [Chemistry 9]

[0377]

[0378] For example, as R 921 ~R 930 In the case of "one or more sets of two or more adjacent groups are bonded to each other to form a ring", one set of two adjacent groups refers to R 921 With R 922 , R 922 With R 923 , R 923 With R 924 , R 924 With R 930 , R 930 With R 925 , R 925 With R 926 , R 926 With R927 , R 927 With R 928 , R 928 With R 929 , and R 929 With R 921 .

[0379] The above “one or more groups” means that two or more groups of the above two adjacent groups can simultaneously form a ring. 921 With R 922 Bonded to each other to form ring A, while R 925 With R 926 When they are bonded to each other to form ring B, they are represented by the following formula (XY-81).

[0380] [Chemistry 10]

[0381]

[0382] When "two or more adjacent pairs" form a ring, for example, R 921 With R 922 Bonded to each other to form ring A, R 922 With R 923 Bonded to each other to form a ring C, formed by R 921 ~R 923 The three adjacent anthracene fused anthracene skeletons have a common R 922 The case of ring A and ring C is represented by the following formula (XY-82).

[0383] [Chemistry 11]

[0384]

[0385] Rings A to C formed in the above formulae (XY-81) and (XY-82) are saturated or unsaturated rings.

[0386] The "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.

[0387] For example, R shown in the above formula (XY-81) 921 With R 922 The ring A formed by bonding to each other means that R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 A ring is formed by bonding a carbon atom of the anthracene skeleton to one or more arbitrary elements. 921 With R 922 In the case of forming ring A, R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton is bonded to form an unsaturated ring with 4 carbon atoms, R921 With R 922 The ring formed is a benzene ring. In addition, when a saturated ring is formed, it is a cyclohexane ring.

[0388] Herein, "arbitrary element" is preferably C element, N element, O element, or S element. In the case of an arbitrary element (for example, C element or N element), the bond not participating in the ring formation may be terminated by a hydrogen atom or the like, or may be substituted by an arbitrary substituent. When an arbitrary element other than C element is contained, the formed ring becomes a heterocycle.

[0389] The number of “one or more arbitrary elements” constituting the saturated or unsaturated 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.

[0390] Specific examples of the aromatic hydrocarbon ring include structures in which the aryl groups listed as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0391] 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.

[0392] Specific examples of the aliphatic hydrocarbon ring include structures in which the cycloalkyl groups listed as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0393] When the above-mentioned "saturated or unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "saturated or unsaturated ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0394] In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (hereinafter, sometimes referred to as "optional substituent") is a group selected from the following:

[0395] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0396] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0397] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0398] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0399] -Si(R 901 )(R 902 )(R 903 )、

[0400] -O-(R 904 )、

[0401] -S-(R 905 )、

[0402] -N(R 906 )(R 907 )

[0403] (In this article,

[0404] R 901 ~R 907 Each independently is:

[0405] Hydrogen atoms,

[0406] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0407] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0408] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0409] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 901 ~R 907 When there are two or more, two or more R 901 ~R 907 They can be the same or different. ),

[0410] Halogen atoms, cyano, nitro,

[0411] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0412] An unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0413] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0414] Alkyl groups having 1 to 50 carbon atoms,

[0415] an aryl group having 6 to 50 ring carbon atoms, and

[0416] A monovalent heterocyclic group having 5 to 50 ring atoms.

[0417] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0418] Alkyl groups having 1 to 18 carbon atoms,

[0419] an aryl group having 6 to 18 ring carbon atoms, and

[0420] A monovalent heterocyclic group having 5 to 18 ring atoms.

[0421] Specific examples of each of the above-mentioned optional substituents are as described above.

[0422] In the present specification, unless otherwise specified, any adjacent substituents may form a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5-membered ring or 6-membered ring, more preferably a benzene ring).

[0423] In the present specification, unless otherwise specified, an arbitrary substituent may further have a substituent. Examples of the substituent further possessed by the arbitrary substituent include the same substituents as those for the above-mentioned arbitrary substituents.

[0424] [Compound represented by formula (1)]

[0425] A compound according to one embodiment of the present invention is represented by the following formula (1).

[0426] [Chemistry 12]

[0427]

[0428] (In formula (1),

[0429] R1~R8 are independently

[0430] Hydrogen atoms,

[0431] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0432] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0433] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0434] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0435] -Si(R 901 )(R 902 )(R 903 ),

[0436] -O-(R 904 ),

[0437] -S-(R 905 ),

[0438] -N(R 906 )(R 907 ),

[0439] Halogen atoms, cyano, nitro,

[0440] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0441] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0442] R 901 ~R 907 Each independently

[0443] Hydrogen atoms,

[0444] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0445] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0446] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0447] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0448] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 Each may be the same or different.

[0449] Two or more adjacent ones of R1 to R8 are not bonded to each other to form a ring.

[0450] Among them, at least one of R1 to R8 is a deuterium atom.

[0451] L1 and L2 are independently

[0452] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0453] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0454] m11 and m12 are each independently an integer of 0 to 4. When m1 and m2 are 0, (L1) m11 and (L2) m12 When m11 or m12 is 2 or more, the two or more m11 or m12 may be the same as or different from each other.

[0455] Ar1 and Ar2 are each independently

[0456] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0457] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0458] Here, at least one of Ar1 and Ar2 is a substituted or unsubstituted condensed aryl group in which only four or more benzene rings are condensed.

[0459] One or more of the hydrogen atoms possessed by one or more groups selected from L1, L2, Ar1 and Ar2 may be deuterium atoms.

[0460] The compound represented by the aforementioned formula (1) has one or more deuterium atoms in the anthracene skeleton, and has a fused aryl group formed by condensing only four or more benzene rings in the side chain, and may also have a deuterium atom in the side chain (including the aforementioned fused aryl group, an aryl group other than the aforementioned fused aryl group, and a monovalent heterocyclic group). By using the compound represented by the aforementioned formula (1) in the light-emitting layer, the effect of improving the device life can be obtained.

[0461] Here, the fused aryl group "formed by condensing only benzene rings" excludes monovalent groups derived from aromatic hydrocarbon rings condensed from rings other than benzene rings. Specifically, for example, monovalent groups derived from benzofluorene rings condensed from 4 benzene rings and one 5-membered ring are excluded.

[0462] In addition, the condensed aryl group in which only benzene rings are condensed may be substituted with any substituent.

[0463] All of R1 to R8 may be deuterium atoms, or a part (for example, 1 or 2) of them may be deuterium atoms.

[0464] In one embodiment, 1 to 8 of R1 to R8 are deuterium atoms. In one embodiment, 1 to 4 of R1 to R8 are deuterium atoms. In addition, in one embodiment, 2 to 8, or 2 to 4 of R1 to R8 are deuterium atoms.

[0465] In one embodiment, all of R1 to R8 are deuterium atoms.

[0466] R1 to R8 that are not deuterium atoms are preferably hydrogen atoms (protium atoms).

[0467] Compounds containing deuterium atoms can be identified by mass spectrometry or 1 H-NMR analysis method was used to confirm the binding position of the deuterium atom in the compound. 1 The H-NMR analysis method is as follows.

[0468] Mass spectrometry analysis of the target compound revealed that the molecular weight increased by 1 compared to a corresponding compound in which all hydrogen atoms were protium atoms, thereby confirming that the compound contained one deuterium atom. 1 H-NMR analysis does not output signals, so the target compound is analyzed by 1 The integral value obtained by H-NMR analysis can confirm the number of deuterium atoms contained in the molecule. 1 H-NMR analysis can determine the bonding position of the deuterium atom through the attribution signal.

[0469] In one embodiment, one of Ar1 and Ar2 is the fused aryl group formed only by the fusion of 4 or more benzene rings as described above.

[0470] In one embodiment, the fused aryl group formed only by the fusion of 4 or more benzene rings is a fused aryl group composed of 4 or more and 6 or less benzene rings.

[0471] In one embodiment, the fused aryl group formed only by the fusion of 4 or more benzene rings is a substituted or unsubstituted monovalent group derived from a polycyclic fused aromatic hydrocarbon selected from the following group.

[0472] Tetracene,

[0473] Pyrene,

[0474] Chrysene,

[0475] Triphenylene,

[0476] Benz[a]anthracene,

[0477] Benzo[a]pyrene,

[0478] Perylene,

[0479] Pentacene,

[0480] Benzo[a]pyrene,

[0481] Benzo[c]triphenylene,

[0482] Dibenz[a,h]anthracene,

[0483] Picene,

[0484] Naphtho[2,1,8,7-defg]chrysene,

[0485] Coronene,

[0486] Dibenzopyrene, and

[0487] Hexabenzocoronene.

[0488] In one embodiment, Ar1-(L1) m11 - and Ar2-(L2) m12 - in formula (1), either one or both are not the group represented by the following formula (BA).

[0489] [Chemical formula 13]

[0490]

[0491] (In formula (BA),

[0492] R A and R B are each independently a substituent.

[0493] Ra As a substituent.

[0494] m is an integer from 0 to 7. When m is 2 or more, multiple R a They can be the same or different.)

[0495] In one embodiment, Ar1-(L1) in formula (1) m11 - and Ar2-(L2) m12 - Either one or both are not substituted or unsubstituted anthracenyl.

[0496] In one embodiment, either or both of Ar1 and Ar2 in formula (1) are not triphenylene groups.

[0497] In one embodiment, (L1) m11 and (L2) m12 Each independently

[0498] single bond,

[0499] Substituted or unsubstituted phenylene,

[0500] Substituted or unsubstituted biphenylene, or

[0501] A substituted or unsubstituted naphthylene group.

[0502] That is, in one embodiment, at least one of m11 and m12 is 0, (L1) m11 and (L2) m12 Each is independently a single bond.

[0503] In one embodiment, at least one of m11 and m12 is 1, and L1 and L2 are each independently

[0504] Substituted or unsubstituted phenylene,

[0505] Substituted or unsubstituted biphenylene, or

[0506] A substituted or unsubstituted naphthylene group.

[0507] In one embodiment, m11 and m12 are 1 or more, (L1) m11 and (L2) m12 Each is independently selected from divalent groups represented by the following formulae (a1) to (a17).

[0508] [Chemistry 14]

[0509]

[0510] [Chemistry 15]

[0511]

[0512] (In formulas (a1) to (a17),

[0513] ** represent the bonding positions to the anthracene skeleton and Ar1 or Ar2, respectively.

[0514] R a As a substituent.

[0515] n1 is an integer ranging from 0 to 4.

[0516] n2 is an integer ranging from 0 to 3.

[0517] n3 is an integer ranging from 0 to 2.

[0518] When n1, n2 and n3 are 2 or more, multiple R a They can be the same or different.)

[0519] In one embodiment, one or both of m11 and m12 are 0, that is, (L1) m11 and (L2) m12 At least one of them is a single bond. In one embodiment, both m11 and m12 are 0. That is, (L1) m11 and (L2) m12 For a single key.

[0520] In one embodiment, at least one of m11 and m12 is 2,

[0521] (L1) m11 and (L2) m12 They are represented by (L1)-(L1) and (L2)-(L2), respectively.

[0522] Multiple L1 and L2 are independently

[0523] Substituted or unsubstituted phenylene, or

[0524] A substituted or unsubstituted naphthylene group.

[0525] In one embodiment, both m11 and m12 are 2.

[0526] In one embodiment, L1 and L2 are each independently selected from divalent groups represented by the following formula.

[0527] [Chemistry 16]

[0528]

[0529] (In the above formula, ** represents the bonding position to the anthracene skeleton and Ar1 or Ar2, respectively.)

[0530] In one embodiment, n1, n2 and n3 in the above formulae (a1) to (a17) are each independently 0. That is, the substituent R a .

[0531] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (1-1).

[0532] [Chemistry 17]

[0533]

[0534] (In formula (1-1), R1 to R8, L1, L2, m11 and m12 are as defined in formula (1) above.

[0535] Ar 1A It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, excluding a condensed aryl group in which only 4 or more benzene rings are condensed.

[0536] Ar 2B It is a condensed aryl group in which only 4 or more and 6 or less benzene rings are condensed.

[0537] Selected from L1, L2, Ar 1A and Ar 2B One or more of the hydrogen atoms in one or more groups in the formula (a) may be deuterium atoms.

[0538] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (1-2).

[0539] [Chemistry 18]

[0540]

[0541] (In formula (1-2), R1 to R8, L2 and m12 are as defined in formula (1).

[0542] Ar 1A It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, excluding a condensed aryl group in which only 4 or more benzene rings are condensed.

[0543] Ar 2B It is a condensed aryl group in which only 4 or more and 6 or less benzene rings are condensed.

[0544] Selected from L2, Ar 1A and Ar 2B One or more of the hydrogen atoms in one or more groups in the formula (a) may be deuterium atoms.

[0545] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (1-3).

[0546] [Chemistry 19]

[0547]

[0548] (In formula (1-3), R1 to R8, L1 and m11 are as defined in formula (1) above.

[0549] Ar 1A It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, excluding a condensed aryl group in which only 4 or more benzene rings are condensed.

[0550] Ar 2B It is a condensed aryl group in which only 4 or more and 6 or less benzene rings are condensed.

[0551] Selected from L1, Ar 1A and Ar 2B One or more of the hydrogen atoms in one or more groups in the formula (a) may be deuterium atoms.

[0552] In one embodiment, the substituted or unsubstituted fused aryl group formed by condensing only four or more benzene rings is a substituted or unsubstituted monovalent group derived from a polycyclic condensed aromatic hydrocarbon selected from the following formulae (b1) to (b4).

[0553] [Chemistry 20]

[0554]

[0555] In one embodiment, the substituted or unsubstituted fused aryl group formed by condensing only four or more benzene rings is a substituted or unsubstituted monovalent group derived from a polycyclic fused aromatic hydrocarbon selected from the above formulae (b2) to (b4).

[0556] In one embodiment, Ar 1A for

[0557] Substituted or unsubstituted phenyl,

[0558] Substituted or unsubstituted naphthyl,

[0559] Substituted or unsubstituted biphenyl, or

[0560] Substituted or unsubstituted phenanthroline.

[0561] In one embodiment, at least one of the hydrogen atoms possessed by at least one group selected from L1, L2, Ar1 and Ar2 is a deuterium atom.

[0562] In one embodiment, at least one of the hydrogen atoms possessed by at least one group selected from Ar1 or Ar2 other than the fused aryl group in which only four or more benzene rings are fused is a deuterium atom.

[0563] In one embodiment, all hydrogen atoms possessed by L1, L2, Ar1, and Ar2 are protium atoms.

[0564] The details of each substituent in the above formulae (1), (a1) to (a17), (1-1), (1-2), (1-3) and (b1) to (b4), and the substituent when referred to as "substituted or unsubstituted", are as described in the [Definition] column of this specification.

[0565] The compound represented by formula (1) can be synthesized by the synthesis method described in the Examples using known substitution reactions and raw materials corresponding to the target compound, thereby synthesizing a compound within the scope of the present invention.

[0566] As specific examples of the compound represented by formula (1), for example, the compounds shown below can be given. In the following specific examples, D represents a deuterium atom.

[0567] [Chemistry 21]

[0568]

[0569] [Chemistry 22]

[0570]

[0571] [Chemistry 23]

[0572]

[0573] [Chemistry 24]

[0574]

[0575] [Chemistry 25]

[0576]

[0577] [Chemistry 26]

[0578]

[0579] [Chemistry 27]

[0580]

[0581] [Chemistry 28]

[0582]

[0583] [Material for organic electroluminescent device comprising a compound represented by formula (1)]

[0584] An organic electroluminescent device material according to one embodiment of the present invention includes a compound represented by the above formula (1).

[0585] In one embodiment, the above-mentioned material for an organic EL device is useful as a host material of a light-emitting layer.

[0586] [Composition containing the compound represented by formula (1)]

[0587] A composition of one embodiment of the present invention comprises the compound represented by the aforementioned formula (1), the total of the compound represented by the aforementioned formula (1) (hereinafter sometimes referred to as a deuterated form) and a compound having the same structure as the compound represented by the aforementioned formula (1) except that it contains only protium atoms as hydrogen atoms (hereinafter sometimes referred to as a protated form), the content ratio of the latter being 99 mol% or less.

[0588] The proportion of protium-containing bodies can be confirmed by mass spectrometry.

[0589] [Organic electroluminescent devices and electronic devices]

[0590] An organic electroluminescent device according to one embodiment of the present invention has

[0591] cathode,

[0592] Anode, and

[0593] a light-emitting layer disposed between the cathode and the anode,

[0594] The light-emitting layer contains the compound represented by the above formula (1).

[0595] In one embodiment, the light-emitting layer further contains a dopant material.

[0596] In one embodiment, the dopant material is one or more compounds selected from the group consisting of a compound represented by the following formula (11), a compound represented by the following formula (21), a compound represented by the following formula (31), a compound represented by the following formula (41), a compound represented by the following formula (51), a compound represented by the following formula (61), a compound represented by the following formula (71), and a compound represented by the following formula (81).

[0597] Reference Figure 1 A schematic configuration of an organic EL element according to one embodiment of the present invention will be described.

[0598] An organic EL element 1 according to one embodiment of the present invention comprises a substrate 2, an anode 3, a light-emitting layer 5, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10. The compound represented by the formula (1) is contained in the light-emitting layer 5.

[0599] In one embodiment, the compound represented by formula (1) and one or more compounds selected from formulas (11), (21), (31), (41), (51), (61), (71) and (81) are contained in the light-emitting layer 5 between the anode 3 and the cathode 10. These compounds may be either a single species or two or more species.

[0600] The compounds represented by formula (11), (21), (31), (41), (51), (61), (71) and (81) are described below.

[0601] (Compound represented by formula (11))

[0602] The compound represented by formula (11) is described.

[0603] [Chemistry 29]

[0604]

[0605] (In formula (11),

[0606] R 101 ~R 110 One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0607] R 101 ~R 110 At least one of them is a monovalent group represented by the following formula (12).

[0608] R which does not form the above-mentioned substituted or unsubstituted saturated or unsaturated ring and is not a monovalent group represented by the following formula (12): 101 ~R 110 Each independently

[0609] Hydrogen atoms,

[0610] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0611] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0612] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0613] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0614] -Si(R 901 )(R 902 )(R 903 ),

[0615] -O-(R 904 ),

[0616] -S-(R 905 ),

[0617] -N(R 906 )(R 907 ),

[0618] Halogen atoms, cyano, nitro,

[0619] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0620] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0621] R 901 ~R 907 As defined in the above formula (1).

[0622] [Chemistry 30]

[0623]

[0624] In formula (12), Ar 101 and Ar 102 Each independently

[0625] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0626] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0627] L 101 ~L 103 Each independently

[0628] single bond,

[0629] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0630] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms. ).

[0631] In formula (11), R 101 ~R 110 Two of them are preferably groups represented by formula (12).

[0632] In one embodiment, the compound represented by formula (11) is represented by the following formula (13).

[0633] [Chemistry 31]

[0634]

[0635] (In formula (13), R 111 ~R 118 R in the above formula (11) which is not a monovalent group represented by the formula (12) 101 ~R 110 Same. 101 ,Ar 102 , L 101 , L 102 and L 103 As defined in the above formula (12).

[0636] In formula (11), L 101 Preferably, a single bond, L 102 and L 103 Preferred is a single bond.

[0637] In one embodiment, the compound represented by formula (11) is represented by the following formula (14) or (15).

[0638] [Chemistry 32]

[0639]

[0640] (In formula (14), R 111 ~R 118 As defined in the above formula (13). 101 ,Ar 102 , L 102 and L 103 As defined in the above formula (12).

[0641] [Chemistry 33]

[0642]

[0643] (In formula (15), R 111 ~R 118 As defined in the above formula (13). 101 and Ar 102 As defined in the above formula (12).

[0644] In formula (11) and formula (12), Ar is preferably 101 and Ar 102 At least one of them is a group represented by the following formula (16).

[0645] [Chemistry 34]

[0646]

[0647] (In formula (16),

[0648] X 101 represents an oxygen atom or a sulfur atom.

[0649] R 121 ~R 127 In the formula (a), one or more adjacent two or more groups are bonded 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.

[0650] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 121 ~R 127 Each independently

[0651] Hydrogen atoms,

[0652] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0653] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0654] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0655] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0656] -Si(R 901 )(R 902 )(R 903 ),

[0657] -O-(R 904 ),

[0658] -S-(R 905 ),

[0659] -N(R 906 )(R 907 ),

[0660] Halogen atoms, cyano, nitro,

[0661] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0662] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0663] R 901 ~R 907 As defined in the above formula (1).

[0664] X 101Preferred is an oxygen atom.

[0665] R 121 ~R 127 At least one of the following is preferred:

[0666] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0667] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0668] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0669] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0670] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0671] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0672] In formula (11) (formula (12)), Ar 101 is a group represented by formula (16), Ar 102 It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0673] In one embodiment, the compound represented by formula (11) is represented by the following formula (17).

[0674] [Chemistry 35]

[0675]

[0676] (In formula (17), R 111 ~R 118 As defined in the above formula (13). 121 ~R 127 As defined in formula (16) above.

[0677] R 131 ~R 135 Each independently

[0678] Hydrogen atoms,

[0679] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0680] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0681] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0682] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0683] -Si(R 901 )(R 902 )(R 903 ),

[0684] -O-(R 904 ),

[0685] -S-(R 905 ),

[0686] -N(R 906 )(R 907 ),

[0687] Halogen atoms, cyano, nitro,

[0688] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0689] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0690] R 901 ~R 907 As defined in the above formula (1).

[0691] As specific examples of the compound represented by formula (11), for example, the following compounds can be given. In the following specific examples, Me represents a methyl group.

[0692] [Chemistry 36]

[0693]

[0694] [Chemistry 37]

[0695]

[0696] [Chemistry 38]

[0697]

[0698] [Chemistry 39]

[0699]

[0700] [Chemistry 40]

[0701]

[0702] [Chemistry 41]

[0703]

[0704] [Chemistry 42]

[0705]

[0706] [Chemistry 43]

[0707]

[0708] (Compound represented by formula (21))

[0709] The compound represented by formula (21) is described.

[0710] [Chemistry 44]

[0711]

[0712] (In formula (21),

[0713] Z is independently CR a or N.

[0714] Ring A1 and ring A2 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[0715] R a When there are multiple R a One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0716] R b When there are multiple R b One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0717] R c When there are multiple R c One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0718] n21 and n22 are each independently an integer of 0 to 4.

[0719] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring a ~R c Each independently

[0720] Hydrogen atoms,

[0721] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0722] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0723] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0724] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0725] -Si(R 901 )(R 902 )(R 903 ),

[0726] -O-(R 904 ),

[0727] -S-(R 905 ),

[0728] -N(R 906 )(R 907 ),

[0729] Halogen atoms, cyano, nitro,

[0730] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0731] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0732] R 901 ~R 907 As defined in the above formula (1).

[0733] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound into which a hydrogen atom is introduced in the above-mentioned "aryl group". The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring contains carbon atoms on the fused bicyclic structure at the center of the two formulas (21) as ring atoms. Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds into which a hydrogen atom is introduced in the "aryl group" described in Specific Example Group G1.

[0734] The "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound into which a hydrogen atom is introduced into the above-mentioned "heterocyclic group". The "heterocycle" of the A1 ring and the A2 ring contains carbon atoms on the fused bicyclic structure at the center of the two formulas (21) as ring atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds into which a hydrogen atom is introduced into the "heterocyclic group" described in Specific Example Group G2.

[0735] R b It is bonded to any carbon atom of the aromatic hydrocarbon ring forming the A1 ring, or any atom of the heterocyclic ring forming the A1 ring.

[0736] R c It is bonded to any carbon atom of the aromatic hydrocarbon ring forming the A2 ring, or any atom of the heterocyclic ring forming the A2 ring.

[0737] R a ~R c Among them, at least one (preferably two) is preferably a group represented by the following formula (21a).

[0738] -L 201 -Ar 201 (21a)

[0739] (In formula (21a),

[0740] L 201 for

[0741] single bond,

[0742] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0743] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0744] Ar 201 for

[0745] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0746] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[0747] A group represented by the following formula (21b).

[0748] [Chemistry 45]

[0749]

[0750] In formula (21b),

[0751] L 211 and L 212 Each independently

[0752] single bond,

[0753] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0754] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[0755] Ar 211 and Ar 212 They are bonded 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.

[0756] Does not form a substituted or unsubstituted saturated or unsaturated ring Ar 211 and Ar 212 Each independently

[0757] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0758] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0759] In one embodiment, the compound represented by formula (21) is represented by the following formula (22).

[0760] [Chemistry 46]

[0761]

[0762] (In formula (22),

[0763] R 201 ~R 211 One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0764] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 201 ~R 211 Each independently

[0765] Hydrogen atoms,

[0766] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0767] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0768] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0769] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0770] -Si(R 901 )(R 902 )(R 903 ),

[0771] -O-(R 904 ),

[0772] -S-(R 905 ),

[0773] -N(R 906 )(R 907 ),

[0774] Halogen atoms, cyano, nitro,

[0775] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0776] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0777] R 901 ~R 907 As defined in the above formula (1).

[0778] R 201 ~R 211 At least one (preferably two) of the above-mentioned groups are preferably a group represented by the above-mentioned formula (21a). 204 and R 211 It is a group represented by the above formula (21a).

[0779] In one embodiment, the compound represented by formula (21) is a compound having a structure represented by the following formula (21-1) or (21-2) bonded to the A1 ring. In another embodiment, the compound represented by formula (22) is a compound having a structure represented by the following formula (21-1) or (21-2) bonded to the A1 ring. 204 ~R 207 A compound having a structure represented by the following formula (21-1) or (21-2) is bonded to the bonded ring.

[0780] [Chemistry 47]

[0781]

[0782] (In formula (21-1), the two *s are each independently bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring or a ring-forming atom of the heterocyclic ring of the A1 ring of formula (21), or to R of formula (22) 204 ~R 207 Any bond of .

[0783] The three *s in formula (21-2) are each independently bonded to a ring-constituting carbon atom of an aromatic hydrocarbon ring or a ring-constituting atom of a heterocyclic ring of the A1 ring in formula (21), or to R 204 ~R 207 Any bond of .

[0784] R 221 ~R 227 and R 231 ~R 239 One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0785] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 221 ~R 227 and R 231 ~R 239 Each independently

[0786] Hydrogen atoms,

[0787] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0788] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0789] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0790] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0791] -Si(R 901 )(R 902 )(R 903 ),

[0792] -O-(R 904 ),

[0793] -S-(R 905 ),

[0794] -N(R 906 )(R 907 ),

[0795] Halogen atoms, cyano, nitro,

[0796] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0797] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0798] R 901 ~R 907 As defined in the above formula (1).

[0799] In one embodiment, the compound represented by formula (21) is a compound represented by the following formula (21-3), formula (21-4) or formula (21-5).

[0800] [Chemistry 48]

[0801]

[0802] (In formula (21-3), formula (21-4) and formula (21-5),

[0803] The A1 ring is as defined in formula (21).

[0804] R 2401 ~R 2407 R of formula (21-1) and (21-2) 221 ~R 227 Same. 2410 ~R 2417 R 201 ~R211 same.).

[0805] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms in the A1 ring of the formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene ring.

[0806] In one embodiment, the substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms in the A1 ring of formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[0807] In one embodiment, the compound represented by formula (21) or formula (22) is selected from the compounds represented by the following formulas (21-6-1) to (21-6-7).

[0808] [Chemistry 49]

[0809]

[0810] (In formula (21-6-1)~(21-6-7),

[0811] R 2421 ~R 2427 R of formula (21-1) and (21-2) 221 ~R 227 Same. 2430 ~R 2437 and R 2441 ~R 2444 R 201 ~R 211 same.

[0812] X is O, NR 901 , or C(R 902 )(R 903 ).

[0813] R 901 ~R 903 As defined in the above formula (1).

[0814] In one embodiment, in the compound represented by formula (22), R 201 ~R 211 In the formula (25), two or more adjacent groups are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.

[0815] (Compound represented by formula (25))

[0816] The compound represented by formula (25) is described.

[0817] [Chemistry 50]

[0818]

[0819] (In formula (25),

[0820] Selected from R 251 With R 252 , R 252 With R 253 , R 254 With R 255 , R 255 With R 256 , R 256 With R 257 , R 258 With R 259 , R 259 With R 260 , and R 260 With R 261 Two or more pairs of the rings are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.

[0821] Among them, R 251 With R 252 The pair composed of 252 With R 253 The pair composed of R 254 With R 255 The pair composed of 255 With R 256 The pair composed of R 255 With R 256 The pair and R 256 With R 257 The pair composed of R 258 With R 259 The pair composed of 259 With R 260 The pair consisting of R 259 With R 260 The pair and R 260 With R 261 The composed pairs do not form rings at the same time.

[0822] R 251 ~R 261 The two or more rings formed may be the same or different.

[0823] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 251 ~R 261 Each independently

[0824] Hydrogen atoms,

[0825] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0826] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0827] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0828] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0829] -Si(R 901 )(R 902 )(R 903 ),

[0830] -O-(R 904 ),

[0831] -S-(R 905 ),

[0832] -N(R 906 )(R 907 ),

[0833] Halogen atoms, cyano, nitro,

[0834] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0835] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0836] R 901 ~R 907 As defined in the above formula (1).

[0837] In formula (25), R n With R n＋1 (n represents an integer selected from 251, 252, 254 to 256, and 258 to 260) are bonded to each other, and R n With R n＋1 The two bonded ring-forming carbon atoms together form a substituted or unsubstituted saturated or unsaturated ring. The ring is preferably composed of atoms selected from C atoms, O atoms, S atoms and N atoms, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.

[0838] The number of the above-mentioned ring structures in the compound represented by formula (25) is, for example, 2, 3, or 4. Two or more ring structures may each exist on the same benzene ring on the mother skeleton of formula (25), or may exist on different benzene rings. For example, when there are three ring structures, one ring structure may exist on each of the three benzene rings of formula (25).

[0839] Examples of the ring structure in the compound represented by formula (25) include structures represented by the following formulae (251) to (260).

[0840] [Chemistry 51]

[0841]

[0842] (In formulas (251) to (257), *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent R n With R n＋1 The two aforementioned ring-forming carbon atoms bonded to R n The ring-forming carbon atoms to be bonded may be any of two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.

[0843] X 2501 C(R 2512 )(R 2513 ), NR 2514 , O or S.

[0844] R 2501 ~R 2506 and R 2512 ~R 2513 One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0845] R does not form a substituted or unsubstituted saturated or unsaturated ring 2501 ~R 2514 With the aforementioned R 251 ~R 261 same.).

[0846] [Chemistry 52]

[0847]

[0848] (In formulas (258) to (260), *1 and *2, and *3 and *4 represent R n With R n＋1 The two aforementioned ring-forming carbon atoms bonded to R n The ring-forming carbon atoms to which the ring is bonded may be any of the two ring-forming carbon atoms represented by *1 and *2, or *3 and *4.

[0849] X 2501 C(R 2512 )(R 2513 ), NR 2514 , O or S.

[0850] R 2515 ~R 2525One or more groups of two or more adjacent groups in the moiety are bonded 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.

[0851] R does not form a substituted or unsubstituted saturated or unsaturated ring 2515 ~R 2521 and R 2522 ~R 2525 With the aforementioned R 251 ~R 261 same.).

[0852] In formula (25), R 252 , R 254 , R 255 , R 260 and R 261 At least one (preferably R 252 , R 255 and R 260 At least one of R 252 ) is preferably a group that does not form a ring structure.

[0853] (i) In formula (25), R n With R n＋1 When the formed ring structure has a substituent,

[0854] (ii) In formula (25), R which does not form a ring structure 251 ~R 261 ,and

[0855] (iii) R in formulas (251) to (260) 2501 ~R 2514 , R 2515 ~R 2525 Preferably, each independently is

[0856] Hydrogen atoms,

[0857] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0858] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0859] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0860] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0861] -N(R 906 )(R 907 ),

[0862] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[0863] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[0864] Any one selected from the following groups.

[0865] [Chemistry 53]

[0866]

[0867] (In formulas (261) to (264), R d Each independently

[0868] Hydrogen atoms,

[0869] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0870] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0871] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0872] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0873] -Si(R 901 )(R 902 )(R 903 ),

[0874] -O-(R 904 ),

[0875] -S-(R 905 ),

[0876] -N(R 906 )(R 907 ),

[0877] Halogen atoms, cyano, nitro,

[0878] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0879] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0880] X is C(R 901 )(R 902 ), NR 903 , O or S.

[0881] R 901 ~R 907 As defined in the above formula (1).

[0882] p1 is an integer of 0 to 5, p2 is an integer of 0 to 4, p3 is an integer of 0 to 3, and p4 is an integer of 0 to 7. ).

[0883] In one embodiment, the compound represented by formula (25) is represented by any of the following formulas (25-1) to (25-6).

[0884] [Chemistry 54]

[0885]

[0886] (In formulas (25-1) to (25-6), rings d to i are each independently a substituted or unsubstituted saturated or unsaturated ring. R 251 ~R 261 Same as the above formula (25).

[0887] In one embodiment, the compound represented by formula (25) is represented by any of the following formulas (25-7) to (25-12).

[0888] [Chemistry 55]

[0889]

[0890] (In formulae (25-7) to (25-12), rings d to f, k, and j are each independently a substituted or unsubstituted saturated or unsaturated ring. R 251 ~R 261 Same as the above formula (25).

[0891] In one embodiment, the compound represented by formula (25) is represented by any of the following formulas (25-13) to (25-21).

[0892] [Chemistry 56]

[0893]

[0894] (In formulas (25-13) to (25-21), rings d to k are each independently a substituted or unsubstituted saturated or unsaturated ring. R 251 ~R 261 Same as the above formula (25).

[0895] When the ring g or h further has a substituent, examples of the substituent include:

[0896] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0897] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0898] A group represented by the above formula (261), (263) or (264).

[0899] In one embodiment, the compound represented by formula (25) is represented by any of the following formulas (25-22) to (25-25).

[0900] [Chemistry 57]

[0901]

[0902] (In formula (25-22)~(25-25), X 250 Each independently is C(R 901 )(R 902 ), NR 903 , O or S. R 251 ~R 261 , R 271 ~R 278 R of the above formula (25) 251 ~R 261 Same. 901 ~R 903 As defined in the above formula (1).

[0903] In one embodiment, the compound represented by formula (25) is represented by the following formula (25-26).

[0904] [Chemistry 58]

[0905]

[0906] (In formula (25-26), X 250 Each independently is C(R 901 )(R 902 ), NR 903 , O or S. R 253 , R 254 , R 257 , R 258 , R 261 , and R 271 ~R 282 R of the above formula (25) 251 ~R 261 Same. 901 ~R 903 As defined in the above formula (1).

[0907] As specific examples of the compound represented by formula (21), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[0908] [Chemistry 59]

[0909]

[0910] [Chemistry 60]

[0911]

[0912] [Chemistry 61]

[0913]

[0914] [Chemistry 62]

[0915]

[0916] [Chemistry 63]

[0917]

[0918] [Chemistry 64]

[0919]

[0920] [Chemistry 65]

[0921]

[0922] [Chemistry 66]

[0923]

[0924] [Chemistry 67]

[0925]

[0926] [Chemistry 68]

[0927]

[0928] (Compound represented by formula (31))

[0929] The compound represented by formula (31) is described below. The compound represented by formula (31) corresponds to the compound represented by formula (21-3).

[0930] [Chemistry 69]

[0931]

[0932] (In formula (31),

[0933] R 301 ~R 307 and R 311 ~R 317 One or more groups of two or more adjacent groups in the group form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0934] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 301 ~R 307 and R 311 ~R 317 Each independently

[0935] Hydrogen atoms,

[0936] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0937] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0938] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0939] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0940] -Si(R 901 )(R 902 )(R 903 ),

[0941] -O-(R 904 ),

[0942] -S-(R 905 ),

[0943] -N(R 906 )(R 907 ),

[0944] Halogen atoms, cyano, nitro,

[0945] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0946] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0947] R 321 and R 322 Each independently

[0948] Hydrogen atoms,

[0949] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0950] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0951] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0952] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0953] -Si(R901 )(R 902 )(R 903 ),

[0954] -O-(R 904 ),

[0955] -S-(R 905 ),

[0956] -N(R 906 )(R 907 ),

[0957] Halogen atoms, cyano, nitro,

[0958] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0959] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0960] R 901 ~R 907 As defined in the above formula (1).

[0961] "R 301 ~R 307 and R 311 ~R 317 A group of two or more adjacent "for example, R 301 With R 302 , R 302 With R 303 , R 303 With R 304 , R 305 With R 306 , R 306 With R 307 , R 301 With R 302 With R 303 And other combinations.

[0962] In one embodiment, R 301 ~R 307 and R 311 ~R 317 At least one, preferably two, of the 906 )(R 907 ) shown in the figure.

[0963] In one embodiment, R 301 ~R 307 and R 311 ~R 317 Each is independently a hydrogen atom, 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.

[0964] In one embodiment, the compound represented by formula (31) is a compound represented by the following formula (32).

[0965] [Chemistry 70]

[0966]

[0967] (In formula (32),

[0968] R 331 ~R 334 and R 341 ~R 344 One or more groups of two or more adjacent groups in the group form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0969] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 331 ~R 334 , R 341 ~R 344 , and R 351 and R 352 Each independently

[0970] Hydrogen atoms,

[0971] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0972] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0973] R 361 ~R 364 Each independently

[0974] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0975] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. ).

[0976] In one embodiment, the compound represented by formula (31) is a compound represented by the following formula (33).

[0977] [Chemistry 71]

[0978]

[0979] (In formula (33), R 351 , R 352 and R 361 ~R 364 As defined in formula (32) above. ).

[0980] In one embodiment, R in formula (32) and (33) 361 ~R 364 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

[0981] In one embodiment, R in formula (31) 321 and R 322 , R in formula (32) and (33) 351 and R 352 A hydrogen atom.

[0982] In one embodiment, the substituent referred to as "substituted or unsubstituted" in formulas (31) to (33) is

[0983] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0984] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0985] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0986] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0987] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0988] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0989] As specific examples of the compound represented by formula (31), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[0990] [Chemistry 72]

[0991]

[0992] [Chemistry 73]

[0993]

[0994] [Chemistry 74]

[0995]

[0996] [Chemistry 75]

[0997]

[0998] [Chemistry 76]

[0999]

[1000] [Chemistry 77]

[1001]

[1002] [Chemistry 78]

[1003]

[1004] [Chemistry 79]

[1005]

[1006] [Chemistry 80]

[1007]

[1008] [Chemistry 81]

[1009]

[1010] [Chemistry 82]

[1011]

[1012] [Chemistry 83]

[1013]

[1014] [Chemistry 84]

[1015]

[1016] [Chemistry 85]

[1017]

[1018] [Chemistry 86]

[1019]

[1020] [Chemistry 87]

[1021]

[1022] [Chemistry 88]

[1023]

[1024] [Chemistry 89]

[1025]

[1026] [Chemistry 90]

[1027]

[1028] [Chemistry 91]

[1029]

[1030] [Chemistry 92]

[1031]

[1032] [Chemistry 93]

[1033]

[1034] [Chemistry 94]

[1035]

[1036] [Chemistry 95]

[1037]

[1038] [Chemistry 96]

[1039]

[1040] [Chemistry 97]

[1041]

[1042] [Chemistry 98]

[1043]

[1044] [Chemistry 99]

[1045]

[1046] [Chemical 100]

[1047]

[1048] (Compound represented by formula (41))

[1049] The compound represented by formula (41) is described.

[1050] [Chemistry 101]

[1051]

[1052] (In formula (41),

[1053] Ring a, ring b and ring c are each independently

[1054] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1055] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1056] R 401 and R 402 Each independently bonds to the aforementioned a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring.

[1057] R which does not form the aforementioned substituted or unsubstituted heterocyclic ring 401 and R 402 Each independently

[1058] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1059] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1060] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1061] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1062] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1063] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. ).

[1064] The a ring, b ring and c ring are rings fused to the fused bicyclic structure at the center of the formula (41) composed of the B atom and two N atoms (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms).

[1065] The "aromatic hydrocarbon ring" of the a ring, the b ring and the c ring has the same structure as the compound into which a hydrogen atom is introduced in the above-mentioned "aryl group". The "aromatic hydrocarbon ring" of the a ring contains three carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring atoms. The "aromatic hydrocarbon ring" of the b ring and the c ring contains two carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring atoms. As specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms", there can be cited compounds into which a hydrogen atom is introduced in the "aryl group" described in the specific example group G1.

[1066] The "heterocycle" of the a ring, b ring and c ring has the same structure as the compound into which a hydrogen atom is introduced in the above-mentioned "heterocyclic group". The "heterocycle" of the a ring contains three carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring atoms. The "heterocycle" of the b ring and the c ring contains two carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring atoms. As specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms", there can be cited compounds into which a hydrogen atom is introduced in the "heterocyclic group" described in the specific example group G2.

[1067] R401 and R 402 Each of them can independently bond to the a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring. In this case, the heterocyclic ring includes the nitrogen atom on the fused bicyclic structure at the center of formula (41). In this case, the heterocyclic ring may contain heteroatoms other than nitrogen atoms. R 401 and R 402 Specifically, the term "bonded to ring a, ring b or ring c" refers to the atoms constituting ring a, ring b or ring c and the atoms constituting R 401 and R 402 For example, R 401 Bonding with the a ring can form a 401 A nitrogen-containing heterocyclic ring having two or more rings fused therein, wherein the ring of is fused to the ring of a. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to heterocyclic groups having two or more nitrogen-containing rings fused therein in specific example group G2.

[1068] R 401 When bonded to the b ring, R 402 When bonded to the a ring, and R 402 The same applies to the case of bonding to the c ring.

[1069] In one embodiment, the ring a, ring b and ring c in formula (41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

[1070] In one embodiment, the ring a, ring b and ring c in formula (41) are each independently a substituted or unsubstituted benzene ring or a naphthalene ring.

[1071] In one embodiment, R in formula (41) 401 and R 402 Each is 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, and is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1072] In one embodiment, the compound represented by formula (41) is a compound represented by the following formula (42).

[1073] [Chemistry 102]

[1074]

[1075] (In formula (42),

[1076] R 401A and selected from R 411 and R 421 One or more of R are bonded to form a substituted or unsubstituted heterocyclic ring, or no substituted or unsubstituted heterocyclic ring is formed. 402A and selected from R413 and R 414 One or more of them are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring.

[1077] R which does not form the aforementioned substituted or unsubstituted heterocyclic ring 401A and R 402A Each independently

[1078] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1079] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1080] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1081] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1082] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1083] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1084] R 411 ~R 421 One or more groups of two or more adjacent groups in the moiety are bonded 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.

[1085] R that does not form the aforementioned substituted or unsubstituted heterocyclic ring or the aforementioned substituted or unsubstituted saturated or unsaturated ring 411 ~R 421 Each independently

[1086] Hydrogen atoms,

[1087] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1088] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1089] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1090] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1091] -Si(R 901 )(R 902 )(R 903 ),

[1092] -O-(R 904 ),

[1093] -S-(R905 ),

[1094] -N(R 906 )(R 907 ),

[1095] Halogen atoms, cyano, nitro,

[1096] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1097] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1098] R 901 ~R 907 As defined in the above formula (1).

[1099] R in formula (42) 401A and R 402A is R in formula (41) 401 and R 402 The corresponding group.

[1100] For example, R 401A Can be used with R 411 The ring containing them is bonded to form a nitrogen-containing heterocyclic ring having two rings (or three rings or more) fused thereto, which is obtained by condensing the benzene ring corresponding to the a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the heterocyclic groups having two or more nitrogen rings fused thereto in the specific example group G2. 401A With R 412 When bonding, R 402A With R 413 When bonding, and R 402A With R 414 The bonding is the same as above.

[1101] R 411 ~R 421 Two or more adjacent groups of R may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. 411 With R 412 The bonds can form a structure condensed with a benzene ring, indole ring, pyrrole ring, benzofuran ring or benzothiophene ring relative to the 6-membered ring to which they are bonded, and the formed condensed ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

[1102] In one embodiment, R which does not contribute to ring formation 411 ~R 421 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1103] In one embodiment, R which does not contribute to ring formation 411 ~R 421 Each is independently a hydrogen atom, 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.

[1104] In one embodiment, R which does not contribute to ring formation 411 ~R 421 Each is independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1105] In one embodiment, R which does not contribute to ring formation 411 ~R 421 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 411 ~R 421 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1106] In one embodiment, the compound represented by the above formula (42) is a compound represented by the following formula (43).

[1107] [Chemistry 103]

[1108]

[1109] (In formula (43),

[1110] R 431 With R 446 R is bonded to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. 433 With R 447 R is bonded to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. 434 With R 451 R is bonded to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. 441 With R 442 They may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1111] R 431 ~R 451 One or more groups of two or more adjacent groups in the moiety are bonded 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.

[1112] R that does not form the aforementioned substituted or unsubstituted heterocyclic ring or the aforementioned substituted or unsubstituted saturated or unsaturated ring 431 ~R 451Each independently

[1113] Hydrogen atoms,

[1114] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1115] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1116] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1117] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1118] -Si(R 901 )(R 902 )(R 903 ),

[1119] -O-(R 904 ),

[1120] -S-(R 905 ),

[1121] -N(R 906 )(R 907 ),

[1122] Halogen atoms, cyano, nitro,

[1123] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1124] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1125] R 901 ~R 907 As defined in the above formula (1).

[1126] R 431 Can be used with R 446 bonded to form a substituted or unsubstituted heterocyclic ring. 431 Can be used with R 446 Bonding to form R 446 A nitrogen-containing heterocyclic ring having three or more rings fused thereto, which is obtained by condensing a benzene ring corresponding to the a-ring and a ring containing N. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more rings fused thereto in the specific example group G2. 433 With R 447 When bonding, R 434 With R 451 When bonding with, and R 441 With R 442 The bonding is the same as above.

[1127] In one embodiment, R which does not contribute to ring formation 431 ~R 451 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1128] In one embodiment, R which does not contribute to ring formation 431 ~R 451 Each is independently a hydrogen atom, 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.

[1129] In one embodiment, R which does not contribute to ring formation 431 ~R 451 Each is independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1130] In one embodiment, R which does not contribute to ring formation 431 ~R 451 are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 431 ~R 451 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1131] In one embodiment, the compound represented by the above formula (43) is a compound represented by the following formula (43A).

[1132] [Chemistry 104]

[1133]

[1134] (In formula (43A),

[1135] R 461 for

[1136] Hydrogen atoms,

[1137] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1138] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1139] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1140] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1141] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1142] R462 ~R 465 Each independently

[1143] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1144] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1145] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1146] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1147] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. ).

[1148] In one embodiment, R 461 ~R 465 Each is independently 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.

[1149] In one embodiment, R 461 ~R 465 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1150] In one embodiment, the compound represented by the above formula (43) is a compound represented by the following formula (43B).

[1151] [Chemistry 105]

[1152]

[1153] (In formula (43B),

[1154] R 471 and R 472 Each independently

[1155] Hydrogen atoms,

[1156] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1157] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1158] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1159] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1160] -N(R 906 )(R 907 ),or

[1161] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1162] R 473 ~R 475 Each independently

[1163] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1164] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1165] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1166] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1167] -N(R 906 )(R 907 ),or

[1168] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1169] R 906 and R 907 As defined in the above formula (1).

[1170] In one embodiment, the compound represented by the above formula (43) is a compound represented by the following formula (43B').

[1171] [Chemistry 106]

[1172]

[1173] (In formula (43B'), R 472 ~R 475 As defined above in formula (43B). ).

[1174] In one embodiment, R 471 ~R 475 At least one of

[1175] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1176] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1177] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1178] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1179] -N(R 906 )(R 907 ),or

[1180] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1181] In one embodiment,

[1182] R 472 for

[1183] Hydrogen atoms,

[1184] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1185] -N(R 906 )(R 907 ),or

[1186] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1187] R 471 and R 473 ~R 475 Each independently

[1188] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1189] -N(R 906 )(R 907 ),or

[1190] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1191] In one embodiment, the compound represented by the above formula (43) is a compound represented by the following formula (43C).

[1192] [Chemistry 107]

[1193]

[1194] (In formula (43C),

[1195] R 481 and R 482 Each independently

[1196] Hydrogen atoms,

[1197] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1198] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1199] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1200] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1201] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1202] R 483 ~R 486 Each independently

[1203] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1204] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1205] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1206] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1207] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. ).

[1208] In one embodiment, the compound represented by the above formula (43) is a compound represented by the following formula (43C′).

[1209] [Chemistry 108]

[1210]

[1211] (In formula (43C'), R 483 ~R 486 As defined above in formula (43C). ).

[1212] In one embodiment, R 481 ~R 486 Each is independently 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.

[1213] In one embodiment, R 481 ~R 486 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1214] The compound represented by formula (41) can firstly prepare an intermediate (first reaction) by bonding the a ring, the b ring and the c ring with a connecting group (a group containing N-R1 and a group containing N-R2), and prepare a final product (second reaction) by bonding the a ring, the b ring and the c ring with a connecting group (a group containing B). In the first reaction, an amination reaction such as the Buchwald-Hartwig reaction can be applied. In the second reaction, a tandem hetero-Friedel-Crafts reaction can be applied.

[1215] Specific examples of the compound represented by formula (41) are described below. These are merely illustrative, and the compound represented by formula (41) is not limited to the following specific examples. In the following specific examples, Me represents a methyl group, tBu represents a tert-butyl group, and D represents a deuterium atom.

[1216] [Chemistry 109]

[1217]

[1218] [Chemistry 110]

[1219]

[1220] [Chemistry 111]

[1221]

[1222] [Chemistry 112]

[1223]

[1224] [Chemistry 113]

[1225]

[1226] [Chemistry 114]

[1227]

[1228] [Chemistry 115]

[1229]

[1230] [Chemistry 116]

[1231]

[1232] [Chemistry 117]

[1233]

[1234] [Chemistry 118]

[1235]

[1236] [Chemistry 119]

[1237]

[1238] [Chemistry 120]

[1239]

[1240] [Chemistry 121]

[1241]

[1242] [Chemistry 122]

[1243]

[1244] [Chemistry 123]

[1245]

[1246] [Chemistry 124]

[1247]

[1248] [Chemistry 125]

[1249]

[1250] [Chemistry 126]

[1251]

[1252] [Chemistry 127]

[1253]

[1254] [Chemistry 128]

[1255]

[1256] (Compound represented by formula (51))

[1257] The compound represented by formula (51) is described.

[1258] [Chemistry 129]

[1259]

[1260] (In formula (51),

[1261] The r ring is a ring represented by the formula (52) or (53) fused at any position of an adjacent ring.

[1262] The q ring and the s ring are each independently a ring represented by the formula (54) fused at any position of the adjacent ring.

[1263] The p ring and the t ring are each independently a structure represented by formula (55) or (56) fused at any position of the adjacent ring.

[1264] R 501 When there are multiple adjacent R 501 They are bonded 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.

[1265] X 501 is an oxygen atom, a sulfur atom, or NR 502 .

[1266] R which does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 501 and R 502 for

[1267] Hydrogen atoms,

[1268] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1269] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1270] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1271] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1272] -Si(R 901 )(R 902 )(R 903 ),

[1273] -O-(R 904 ),

[1274] -S-(R 905 ),

[1275] -N(R 906 )(R 907 ),

[1276] Halogen atoms, cyano, nitro,

[1277] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1278] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1279] R 901 ~R 907 As defined in the above formula (1).

[1280] Ar 501 and Ar 502 Each independently

[1281] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1282] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1283] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1284] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1285] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1286] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1287] L 501 for

[1288] a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

[1289] a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

[1290] a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

[1291] a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,

[1292] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[1293] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.

[1294] m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3 is an integer of 0 to 3, and m4 is an integer of 0 to 5. 501 When there are multiple R 501 They can be the same or different from each other. ).

[1295] In formula (51), each of the p-ring to the t-ring shares two carbon atoms with the adjacent ring and is fused. The position and direction of fusion are not limited, and the fusion can be performed at any position and direction.

[1296] In one embodiment, in the formula (52) or (53) of the r ring, R 501 A hydrogen atom.

[1297] In one embodiment, the compound represented by formula (51) is represented by any of the following formulas (51-1) to (51-6).

[1298] [Chemistry 130]

[1299]

[1300] (In formula (51-1)~(51-6), R 501 , X 501 ,Ar 501 ,Ar 502 , L 501, m1 and m3 are as defined in the above formula (51). ).

[1301] In one embodiment, the compound represented by formula (51) is represented by any of the following formulas (51-11) to (51-13).

[1302] [Chemistry 131]

[1303]

[1304] (In formula (51-11)~(51-13), R 501 , X 501 ,Ar 501 ,Ar 502 , L 501 , m1, m3 and m4 are as defined in the above formula (51). ).

[1305] In one embodiment, the compound represented by formula (51) is represented by any of the following formulas (51-21) to (51-25).

[1306] [Chemistry 132]

[1307]

[1308] (In formula (51-21)~(51-25), R 501 , X 501 ,Ar 501 ,Ar 502 , L 501 , m1 and m4 are as defined in the above formula (51). ).

[1309] In one embodiment, the compound represented by formula (51) is represented by any of the following formulas (51-31) to (51-33).

[1310] [Chemistry 133]

[1311]

[1312] (In formula (51-31)~(51-33), R 501 , X 501 ,Ar 501 ,Ar 502 , L 501 , m2~m4 are as defined in the above formula (51). ).

[1313] In one embodiment, Ar 501 and Ar 502 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1314] In one embodiment, Ar 501 and Ar 502 One of them is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1315] As specific examples of the compound represented by formula (51), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[1316] [Chemistry 134]

[1317]

[1318] [Chemistry 135]

[1319]

[1320] [Chemistry 136]

[1321]

[1322] [Chemistry 137]

[1323]

[1324] [Chemistry 138]

[1325]

[1326] [Chemistry 139]

[1327]

[1328] (Compound represented by formula (61))

[1329] The compound represented by formula (61) is described.

[1330] [Chemistry 140]

[1331]

[1332] (In formula (61),

[1333] R 601 With R 602 , R 602 With R 603 , and R 603 With R 604 At least one group of them are bonded to each other to form a divalent group represented by the following formula (62).

[1334] R 605 With R 606 , R 606 With R607 , and R 607 With R 608 At least one group of them are bonded to each other to form a divalent group represented by the following formula (63).

[1335] [Chemistry 141]

[1336]

[1337] R 601 ~R 604 A group which does not form a divalent group represented by the above formula (62), and R 611 ~R 614 At least one of them is a monovalent group represented by the following formula (64).

[1338] R 605 ~R 608 A group which does not form a divalent group represented by the above formula (63), and R 621 ~R 624 At least one of them is a monovalent group represented by the following formula (64).

[1339] X 601 is an oxygen atom, a sulfur atom, or NR 609 .

[1340] R which does not form a divalent group represented by the above formulae (62) and (63) and is not a monovalent group represented by the above formula (64) 601 ~R 608 , R is not a monovalent group represented by the above formula (64) 611 ~R 614 and R 621 ~R 624 , and R 609 Each independently

[1341] Hydrogen atoms,

[1342] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1343] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1344] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1345] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1346] -Si(R 901 )(R 902 )(R 903 ),

[1347] -O-(R 904 ),

[1348] -S-(R 905 ),

[1349] -N(R 906 )(R 907 ),

[1350] Halogen atoms, cyano, nitro,

[1351] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1352] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1353] R 901 ~R 907 As defined in the above formula (1).

[1354] [Chemistry 142]

[1355]

[1356] In formula (64), Ar 601 and Ar 602 Each independently

[1357] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1358] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1359] L 601 ~L 603 Each independently

[1360] single bond,

[1361] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[1362] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[1363] These are bonded together to form a divalent linking group. ).

[1364] In formula (61), the position where the divalent group represented by formula (62) and the divalent group represented by formula (63) are formed is not particularly limited, and can be 601 ~R 608 The group is formed at the possible position.

[1365] In one embodiment, the compound represented by formula (61) is represented by any of the following formulas (61-1) to (61-6).

[1366] [Chemistry 143]

[1367]

[1368] (In formula (61-1)~(61-6), X 601 As defined above in formula (61).

[1369] R 601 ~R 624 At least two of them are monovalent groups represented by the above formula (64).

[1370] R is not a monovalent group represented by the above formula (64) 601 ~R 624 Each independently

[1371] Hydrogen atoms,

[1372] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1373] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1374] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1375] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1376] -Si(R 901 )(R 902 )(R 903 ),

[1377] -O-(R 904 ),

[1378] -S-(R 905 ),

[1379] -N(R 906 )(R 907 ),

[1380] Halogen atoms, cyano, nitro,

[1381] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1382] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1383] R 901 ~R 907 As defined in the above formula (1).

[1384] In one embodiment, the compound represented by formula (61) is represented by any of the following formulas (61-7) to (61-18).

[1385] [Chemistry 144]

[1386]

[1387] (In formulas (61-7) to (61-18), X 601 As defined in the above formula (61). * is a single bond to the monovalent group represented by the above formula (64). 601 ~R 624 R which is not a monovalent group represented by formula (64) 601 ~R 624 same.).

[1388] R which does not form a divalent group represented by the above formulae (62) and (63) and is not a monovalent group represented by the above formula (64) 601 ~R 608 , and R which is not a monovalent group represented by the above formula (64) 611 ~R 614 and R 621 ~R 624 Preferably, each independently is

[1389] Hydrogen atoms,

[1390] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1391] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1392] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1393] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1394] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1395] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1396] The monovalent group represented by formula (64) is preferably represented by the following formula (65) or (66).

[1397] [Chemistry 145]

[1398]

[1399] (In formula (65), R 631 ~R 640 Each independently

[1400] Hydrogen atoms,

[1401] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1402] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1403] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1404] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1405] -Si(R 901 )(R 902 )(R 903 ),

[1406] -O-(R 904 ),

[1407] -S-(R 905 ),

[1408] -N(R 906 )(R 907 ),

[1409] Halogen atoms, cyano, nitro,

[1410] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1411] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1412] R 901 ~R 907 As defined in the above formula (1).

[1413] [Chemistry 146]

[1414]

[1415] (In formula (66), Ar 601 , L 601 and L 603 As defined above in formula (64). 601 It is a structure represented by the following formula (67).

[1416] [Chemistry 147]

[1417]

[1418] In formula (67), X 602 is an oxygen atom or a sulfur atom.

[1419] R 641 ~R 648 Any one of which is L 603 Single bond bonding.

[1420] R is not a single bond 641~R 648 Each independently

[1421] Hydrogen atoms,

[1422] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1423] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1424] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1425] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1426] -Si(R 901 )(R 902 )(R 903 ),

[1427] -O-(R 904 ),

[1428] -S-(R 905 ),

[1429] -N(R 906 )(R 907 ),

[1430] Halogen atoms, cyano, nitro,

[1431] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1432] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1433] R 901 ~R 907 As defined in the above formula (1).

[1434] As the compound represented by formula (61), in addition to the compounds described in International Publication No. 2014 / 104144, the following compounds can be given as specific examples. In the following specific examples, Me represents a methyl group.

[1435] [Chemistry 148]

[1436]

[1437] [Chemistry 149]

[1438]

[1439] [Chemistry 150]

[1440]

[1441] [Chemistry 151]

[1442]

[1443] [Chemistry 152]

[1444]

[1445] [Chemistry 153]

[1446]

[1447] [Chemistry 154]

[1448]

[1449] [Chemistry 155]

[1450]

[1451] [Chemistry 156]

[1452]

[1453] [Chemistry 157]

[1454]

[1455] [Chemistry 158]

[1456]

[1457] [Chemistry 159]

[1458]

[1459] [Chemistry 160]

[1460]

[1461] [Chemistry 161]

[1462]

[1463] [Chemistry 162]

[1464]

[1465] [Chemistry 163]

[1466]

[1467] [Chemistry 164]

[1468]

[1469] [Chemistry 165]

[1470]

[1471] [Chemistry 166]

[1472]

[1473] [Chemistry 167]

[1474]

[1475] [Chemistry 168]

[1476]

[1477] [Chemistry 169]

[1478]

[1479] [Chemistry 170]

[1480]

[1481] [Chemistry 171]

[1482]

[1483] [Chemistry 172]

[1484]

[1485] [Chemistry 173]

[1486]

[1487] [Chemistry 174]

[1488]

[1489] (Compound represented by formula (71))

[1490] The compound represented by formula (71) is described.

[1491] [Chemistry 175]

[1492]

[1493] (In formula (71),

[1494] A 701 Ring and A 702 The rings are independently

[1495] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1496] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1497] Selected from A 701 Ring and A 702 One or more of the rings are bonded to the bonding site * of the structure represented by the following formula (72).

[1498] [Chemistry 176]

[1499]

[1500] In formula (72),

[1501] A 703 The rings are independently

[1502] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1503] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1504] X 701 NR 703 , C(R 704 )(R 705 )、Si(R 706 )(R 707 )、Ge(R 708 )(R 709 ), O, S or Se.

[1505] R 701 and R 702 They are bonded 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.

[1506] R does not form a substituted or unsubstituted saturated or unsaturated ring 701 and R 702 , and R 703 ~R 709 Each independently

[1507] Hydrogen atoms,

[1508] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1509] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1510] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1511] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1512] -Si(R901 )(R 902 )(R 903 ),

[1513] -O-(R 904 ),

[1514] -S-(R 905 ),

[1515] -N(R 906 )(R 907 ),

[1516] Halogen atoms, cyano, nitro,

[1517] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1518] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1519] R 901 ~R 907 As defined in the above formula (1).

[1520] Selected from A 701 Ring and A 702 One or more of the rings are bonded to * in the structure represented by formula (72). That is, in one embodiment, A 701 The carbon atom of the aromatic hydrocarbon ring or the heterocyclic ring of the ring is bonded to the * of the structure represented by formula (72). 702 A carbon atom constituting the aromatic hydrocarbon ring or a ring atom constituting the heterocyclic ring of the ring is bonded to * of the structure represented by formula (72).

[1521] In one embodiment, in A 701 Ring and A 702 A group represented by the following formula (73) is bonded to either or both of the rings.

[1522] [Chemistry 177]

[1523]

[1524] (In formula (73), Ar 701 and Ar 702 Each independently

[1525] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1526] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1527] L 701 ~L 703Each independently

[1528] single bond,

[1529] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[1530] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[1531] These are bonded together to form a divalent linking group. ).

[1532] In one embodiment, except A 701 Outside the ring, A 702 The carbon atoms of the aromatic hydrocarbon ring or the heterocyclic ring are bonded to the * of the structure represented by formula (72). In this case, the structures represented by formula (72) may be the same or different.

[1533] In one embodiment, R 701 and R 702 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1534] In one embodiment, R 701 and R 702 They bond with each other to form a fluorene structure.

[1535] In one embodiment, Ring A 701 and Ring A 702 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[1536] In one embodiment, Ring A 703 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

[1537] In one embodiment, X 701 It is O or S.

[1538] As specific examples of the compound represented by formula (71), for example, the compounds shown below can be given. In the following specific examples, Me represents a methyl group.

[1539] [Chemical 178]-[Chemical 181].

[1540] (Compound represented by formula (81))

[1541] The compound represented by formula (81) is described.

[1542] [Chemistry 182]

[1543]

[1544] (In formula (81),

[1545] A 801 The ring is a ring represented by the formula (82) fused at any position of an adjacent ring.

[1546] A 802 The ring is a ring represented by formula (83) fused at any position of the adjacent ring. 803 The ring is bonded at any position.

[1547] X 801 and X 802 Each independently is C(R 803 )(R 804 )、Si(R 805 )(R 806 ), an oxygen atom, or a sulfur atom.

[1548] A 803 The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1549] Ar 801 It is 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.

[1550] R 801 ~R 806 Each independently

[1551] Hydrogen atoms,

[1552] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1553] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1554] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1555] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1556] -Si(R 901 )(R 902 )(R 903 ),

[1557] -O-(R 904 ),

[1558] -S-(R 905 ),

[1559] -N(R 906 )(R 907 ),

[1560] Halogen atoms, cyano, nitro,

[1561] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1562] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1563] R 901 ~R 907 As defined in the above formula (1).

[1564] m801 and m802 are each independently an integer from 0 to 2. When they are 2, multiple R 801 or R 802 They can be the same as or different from each other.

[1565] a801 is an integer from 0 to 2. When a801 is 0 or 1, the structures in the brackets shown by "3-a801" may be the same or different. When a801 is 2, Ar 801 They can be the same or different from each other. ).

[1566] In one embodiment, Ar 801 It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1567] In one embodiment, Ring A 803 It is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[1568] In one embodiment, R 803 and R 804 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1569] In one implementation, a801 is 1.

[1570] Specific examples of the compound represented by formula (81) include the following compounds.

[1571] [Chemistry 183]

[1572]

[1573] Specific examples of the above-mentioned groups are described in the [Definition] column of the present specification.

[1574] The organic EL element involved in one embodiment of the present invention has a cathode, an anode and a light-emitting layer arranged between the cathode and the anode as described above. In addition to containing the compound represented by the above formula (1), the light-emitting layer can be made of conventionally known materials and element structures as long as the effects of the present invention are not impaired.

[1575] In addition, in one embodiment, the light-emitting layer further contains one or more compounds selected from the compounds represented by the aforementioned formulas (11), (21), (31), (41), (51), (61), (71) and (81) as dopant materials, and can be made of conventionally known materials and element structures as long as the effects of the present invention are not impaired.

[1576] The content of the compound represented by formula (1) in the light-emitting layer is preferably 1% by mass or more and 20% by mass or less relative to the entire light-emitting layer. In addition, the content of the compound represented by formula (11) in the light-emitting layer is preferably 80% by mass or more and 99% by mass or less relative to the entire light-emitting layer.

[1577] One embodiment of the organic EL device of the present invention preferably includes a hole transport layer between the anode and the light-emitting layer.

[1578] One embodiment of the organic EL device of the present invention preferably has an electron transport layer between the cathode and the light-emitting layer.

[1579] The layer structure of the organic EL element according to one embodiment of the present invention will be described below.

[1580] An organic EL element according to one embodiment of the present invention has an organic layer between a pair of electrodes including a cathode and an anode. The organic layer includes at least one layer including an organic compound. Alternatively, the organic layer is stacked with a plurality of layers including organic compounds. The organic layer may include a layer consisting of only one or more organic compounds. The organic layer may include a layer including both an organic compound and an inorganic compound. The organic layer may include a layer consisting of only one or more inorganic compounds.

[1581] At least one of the layers included in the organic layer is a light-emitting layer. The organic layer can be configured as one light-emitting layer, for example, and can also contain other layers that can be used in the layer structure of the organic EL element. The layers that can be used in the layer structure of the organic EL element are not particularly limited, and examples thereof include a hole transport band region (hole transport layer, hole injection layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light-emitting layer, a light-emitting layer, a spacer layer, an electron transport band region (electron transport layer, electron injection layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer, and the like.

[1582] The organic EL element according to one embodiment of the present invention may be a single-color fluorescent or phosphorescent light-emitting element, or a fluorescent / phosphorescent mixed white light-emitting element, and may be a single type having a single light-emitting unit or a series type having a plurality of light-emitting units.

[1583] The “light-emitting unit” refers to a minimum unit including organic layers, at least one of which is a light-emitting layer, and which emits light by recombination of injected holes and electrons.

[1584] In addition, the "light-emitting layer" described in this specification is an organic layer having a light-emitting function. The light-emitting layer is, for example, a phosphorescent light-emitting layer, a fluorescent light-emitting layer, etc., and may be a single layer or multiple layers.

[1585] The light-emitting unit may be a stacked type having a plurality of phosphorescent light-emitting layers and fluorescent light-emitting layers. In this case, for example, a spacer layer may be provided between the light-emitting layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer.

[1586] As a single-type organic EL element, there is mentioned, for example, an element structure of anode / light-emitting unit / cathode.

[1587] A representative layer structure of the light-emitting unit is shown below. The layers in parentheses are optional.

[1588] (a) (hole injection layer / ) hole transport layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[1589] (b) (hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer)

[1590] (c) (hole injection layer / hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer ( / electron transport layer / electron injection layer)

[1591] (d) (hole injection layer / hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer ( / electron transport layer / electron injection layer)

[1592] (e) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[1593] (f) (hole injection layer / hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / spacer layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[1594] (g) (hole injection layer / hole transport layer / first phosphorescent emitting layer / spacer layer / second phosphorescent emitting layer / spacer layer / fluorescent emitting layer ( / electron transport layer / electron injection layer)

[1595] (h) (hole injection layer / ) hole transport layer / phosphorescent emitting layer / spacer layer / first fluorescent emitting layer / second fluorescent emitting layer ( / electron transport layer / electron injection layer)

[1596] (i) (hole injection layer / ) hole transport layer / electron blocking layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[1597] (j) (hole injection layer / ) hole transport layer / electron blocking layer / phosphorescent light emitting layer ( / electron transport layer / electron injection layer)

[1598] (k) (hole injection layer / ) hole transport layer / exciton blocking layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[1599] (l) (hole injection layer / hole transport layer / exciton blocking layer / phosphorescent light emitting layer ( / electron transport layer / electron injection layer)

[1600] (m) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer ( / electron transport layer / electron injection layer)

[1601] (n) (hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent light emitting layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[1602] (o) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer ( / electron transport layer / electron injection layer)

[1603] (p) (hole injection layer / ) first hole transport layer / second hole transport layer / phosphorescent light emitting layer ( / first electron transport layer / second electron transport layer / electron injection layer)

[1604] (q) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / hole blocking layer ( / electron transport layer / electron injection layer)

[1605] (r) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / hole blocking layer ( / electron transport layer / electron injection layer)

[1606] (s) (hole injection layer / ) hole transport layer / fluorescent light emitting layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[1607] (t) (hole injection layer / ) hole transport layer / phosphorescent light emitting layer / exciton blocking layer ( / electron transport layer / electron injection layer)

[1608] Among them, the layer constitution of the organic EL element involved in one embodiment of the present invention is not limited to them. For example, when the organic EL element has a hole injection layer and a hole transport layer, the hole injection layer is preferably provided between the hole transport layer and the anode. In addition, when the organic EL element has an electron injection layer and an electron transport layer, the electron injection layer is preferably provided between the electron transport layer and the cathode. In addition, the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer can each be composed of one layer or a plurality of layers.

[1609] Multiple phosphorescent light-emitting layers, and phosphorescent light-emitting layers and fluorescent light-emitting layers can be light-emitting layers of different colors. For example, the light-emitting unit (f) can also be set as a hole transport layer / a first phosphorescent light-emitting layer (red light-emitting) / a second phosphorescent light-emitting layer (green light-emitting) / a spacer layer / a fluorescent light-emitting layer (blue light-emitting) / an electron transport layer.

[1610] It should be noted that an electron blocking layer may be provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer may be provided between each light-emitting layer and the electron transport layer. By providing an electron blocking layer or a hole blocking layer, electrons or holes are confined in the light-emitting layer, the recombination probability of the charges in the light-emitting layer is increased, and the luminous efficiency can be improved.

[1611] A typical device structure of a tandem organic EL device is, for example, a device structure of anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode.

[1612] The first light-emitting unit and the second light-emitting unit can be independently selected from the above-mentioned light-emitting units, for example.

[1613] The intermediate layer is generally referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron removal layer, a connection layer, a connection layer, or an intermediate insulating layer. The intermediate layer is a layer that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit, and can be formed of a known material.

[1614] Only one of the first light-emitting unit and the second light-emitting unit may be the light-emitting layer of one embodiment of the present invention, or both may be the light-emitting layer of one embodiment of the present invention.

[1615] The functions, materials, etc. of each layer of the organic EL element described in this specification are described below.

[1616] (Substrate)

[1617] The substrate is used as a support for the organic EL element. The transmittance of light in the visible light region of 400 to 700 nm of the substrate is preferably 50% or more, and a smooth substrate is preferred. As the material of the substrate, for example, soda-lime glass, aluminum silicate glass, quartz glass, plastic, etc. can be cited. In addition, as the substrate, a flexible substrate can be used. A flexible substrate refers to a (flexible) substrate that can be bent, and for example, a plastic substrate can be cited. Specific examples of materials forming the plastic substrate include polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, etc. In addition, an inorganic vapor-deposited film can also be used.

[1618] (anode)

[1619] As the anode, for example, it is preferred to use a metal, alloy, conductive compound, and mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples of the material of the anode include indium oxide-tin oxide (ITO: IndiumTinOxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide or zinc oxide, graphene, etc. In addition, gold, silver, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, and nitrides of these metals (e.g., titanium nitride), etc.

[1620] The anode is usually formed by forming a film of these materials on a substrate by sputtering. For example, a target material in which 1 to 10% by mass of zinc oxide is added to indium oxide can be used to form indium oxide-zinc oxide by sputtering. In addition, for example, a target material in which 0.5 to 5% by mass of tungsten oxide or 0.1 to 1% by mass of zinc oxide is added to indium oxide can be used to form indium oxide containing tungsten oxide or zinc oxide by sputtering.

[1621] As other methods for forming the anode, for example, vacuum deposition, coating, inkjet, spin coating, etc. can be mentioned. For example, when silver paste is used, coating, inkjet, etc. can be used.

[1622] It should be noted that the hole injection layer formed in contact with the anode can be formed using a material that easily injects holes regardless of the work function of the anode. Therefore, general electrode materials such as metals, alloys, conductive compounds, and mixtures thereof can be used in the anode. Specifically, alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (such as magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium; alloys containing rare earth metals, etc., can also be used for the anode.

[1623] (Hole Injection Layer)

[1624] The hole injection layer is a layer containing a substance with high hole injection property, and has the function of injecting holes from the anode to the organic layer. As a substance with high hole injection property, for example, 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, electron-withdrawing (acceptor) compounds, polymer compounds (oligomers, dendrimers, polymers, etc.) etc. can be cited. Among them, aromatic amine compounds, acceptor compounds, more preferably acceptor compounds, can be cited.

[1625] Specific examples of the aromatic amine compound include 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNT PD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc.

[1626] As acceptor compounds, for example, heterocyclic derivatives having an electron-withdrawing group, quinone derivatives having an electron-withdrawing group, aryl borane derivatives, heteroaryl borane derivatives, etc. are preferred. Specific examples include hexacyanohexaazatriphenylene, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (abbreviation: F4TCNQ), 1,2,3-tris[(cyano)(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane, etc.

[1627] When an acceptor compound is used, the hole injection layer preferably further contains a host material. As the host material, a known material used as a material for an organic EL element can be used, and for example, an electron donating (donor) compound is preferably used.

[1628] (Hole Transport Layer)

[1629] The hole transport layer is a layer containing a substance with a high hole transport property, and has a function of transporting holes from the anode to the organic layer.

[1630] As a substance with high hole transport property, it is preferable to have 10 -6 cm 2 Examples of substances having a hole mobility of 100 Å / (V·s) or more include aromatic amine compounds, carbazole derivatives, anthracene derivatives, and polymer compounds.

[1631] Specific examples of the aromatic amine compound include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), -2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), etc.

[1632] Specific examples of carbazole derivatives include 4,4′-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviation: PCzPA).

[1633] Specific examples of the anthracene derivatives include 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).

[1634] Specific examples of the polymer compound include poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA).

[1635] Any substance other than these may be used for the hole transport layer as long as it is a compound with higher hole transport property than electron transport property.

[1636] The hole transport layer may be a single layer or may be a stack of two or more layers. In this case, it is preferred to arrange a layer containing a substance having a larger energy gap among substances with high hole transport properties on the side close to the light emitting layer.

[1637] (Luminous layer)

[1638] The light-emitting layer is a layer containing a substance with high light-emitting property (dopant material). As the dopant material, various materials can be used, for example, fluorescent compounds (fluorescent dopants), phosphorescent compounds (phosphorescent dopants), etc. can be used. Fluorescent compounds are compounds that can emit light from a singlet excited state, and the light-emitting layer containing them is called a fluorescent light-emitting layer. In addition, phosphorescent compounds are compounds that can emit light from a triplet excited state, and the light-emitting layer containing them is called a phosphorescent light-emitting layer.

[1639] The light-emitting layer usually contains a dopant material and a host material for making it emit light efficiently. It should be noted that the dopant material is sometimes referred to as a guest material, an emitter, or a light-emitting material according to the literature. In addition, the host material is sometimes referred to as a matrix material according to the literature.

[1640] One light-emitting layer may contain a plurality of dopant materials and a plurality of host materials. In addition, there may be a plurality of light-emitting layers.

[1641] In this specification, the host material combined with the fluorescent dopant is called "fluorescent host", and the host material combined with the phosphorescent dopant is called "phosphorescent host". It should be noted that the fluorescent host and the phosphorescent host are not only distinguished by molecular structure. The so-called phosphorescent host is a material that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, but it does not mean that it cannot be used as a material for forming a fluorescent light-emitting layer. The same is true for the fluorescent host.

[1642] The content of the dopant material in the light-emitting layer is not particularly limited, but is, for example, preferably 0.1 to 70 mass %, more preferably 0.1 to 30 mass %, further preferably 1 to 30 mass %, further preferably 1 to 20 mass %, and particularly preferably 1 to 10 mass %, from the viewpoint of sufficient light emission and concentration extinction.

[1643] <Fluorescent dopant>

[1644] As fluorescent dopants, fluorescent dopants that can be used together with the fluorescent dopants used in one embodiment of the present invention include, for example, fused polycyclic aromatic derivatives, styrylamine derivatives, fused ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc. Among them, fused ring amine derivatives, boron-containing compounds, and carbazole derivatives are preferred.

[1645] Examples of the fused ring amine derivatives include diaminopyrene derivatives, diaminochrysene derivatives, diaminoanthracene derivatives, diaminofluorene derivatives, and diaminofluorene derivatives obtained by ring-condensing one or more benzofuran skeletons.

[1646] Examples of the boron-containing compound include methylene pyrrole derivatives and triphenylborane derivatives.

[1647] As a blue fluorescent dopant, as a fluorescent dopant that can be used together with the fluorescent dopant used in one embodiment of the present invention, for example, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specifically, N, N'-bis [4- (9H-carbazole-9-yl) phenyl] -N, N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4- (9H-carbazole-9-yl) -4'- (10-phenyl-9-anthracenyl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthracenyl) -4'- (9-phenyl-9H-carbazole-3-yl) triphenylamine (abbreviation: PCBAPA), etc. can be mentioned.

[1648] As green fluorescent dopants, as fluorescent dopants that can be used together with the fluorescent dopant used in one embodiment of the present invention, for example, aromatic amine derivatives can be mentioned. Specifically, N-(9,10-diphenyl-2-anthracenyl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as: 2PCABPhA), N-(9,10-diphenyl-2-anthracenyl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPAPhA), PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthracenyl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviated as 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviated as DPhAPhA), etc.

[1649] Examples of red fluorescent dopants include naphthacene derivatives, diamine derivatives, etc. Specifically, examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD), etc.

[1650] <Phosphorescent dopant>

[1651] Examples of the phosphorescent dopant include phosphorescent heavy metal complexes and phosphorescent rare earth metal complexes.

[1652] Examples of the heavy metal complex include iridium complexes, osmium complexes, platinum complexes, etc. The heavy metal complex is preferably an ortho-metalated complex of a metal selected from iridium, osmium, and platinum.

[1653] As the rare earth metal complex, for example, terbium complex and europium complex can be mentioned. Specifically, terbium (III) tris(acetylacetonate) (monophenanthroline) (abbreviated as Tb(acac)3(Phen)), europium (III) tris(1,3-diphenyl-1,3-propanedione) (monophenanthroline) (abbreviated as Eu(DBM)3(Phen)), europium (III) tris[1-(2-thenoyl)-3,3,3-trifluoroacetonate] (monophenanthroline) (abbreviated as Eu(TTA)3(Phen)) can be mentioned. Since these rare earth metal complexes utilize electron migration between different multiplets to make rare earth metal ions emit light, they are preferably used as phosphorescent dopants.

[1654] Examples of blue phosphorescent dopants include iridium complexes, osmium complexes, platinum complexes, etc. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridinium-N,C2']tetrakis(1-pyrazolyl)borate iridium(III) (abbreviated as FIr6), bis[2-(4',6'-difluorophenyl)pyridinium-N,C2']picolinate iridium(III) (abbreviated as FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinium-N,C2']picolinate iridium(III) (abbreviated as Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridinium-N,C2']acetylacetonate iridium(III) (abbreviated as FIracac), etc.

[1655] As green phosphorescent dopants, for example, iridium complexes can be mentioned. Specifically, tris(2-phenylpyridinium-N, C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridinium-N, C2')iridium(III) acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolium)iridium(III) acetylacetonate (abbreviated as Ir(pbi)2(acac)), bis(benzo[h]quinolinium)iridium(III) acetylacetonate (abbreviated as Ir(bzq)2(acac)), and the like can be mentioned.

[1656] Examples of red phosphorescent dopants include iridium complexes, platinum complexes, terbium complexes, and europium complexes. Specifically, examples include bis[2-(2'-benzo[4,5-α]thienyl)pyridinium-N,C3']acetylacetonate iridium(III) (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinium-N,C2')acetylacetonate iridium(III) (abbreviation: Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP).

[1657] <Main material>

[1658] As the host material, as the host material that can be used together with the host material used in one embodiment of the present invention, for example, metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; heterocyclic compounds such as indole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; condensed aromatic compounds such as naphthalene derivatives, triphenylene derivatives, carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives, tetracene derivatives, and fluoranthene derivatives; aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives, etc. The host material can be used in combination with multiple types.

[1659] Specific examples of the metal complex include tris(8-quinolinol)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinol)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinolato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinol)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-quinolinol)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ), and the like.

[1660] Specific examples of heterocyclic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and the like.

[1661] Specific examples of the condensed aromatic compound include 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (abbreviated as DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviated as DNA), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviated as DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviated as DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (abbreviated as TPB3), 9,10-diphenylanthracene (abbreviated as DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, etc.

[1662] Specific examples of the aromatic amine compound include N,N-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthracenyl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthracenyl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2- The following are some examples of the compounds: anthracene)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4'-bis[N-(spiro-9,9'-difluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB), etc.

[1663] As the fluorescent host, a compound having a higher singlet energy level than the fluorescent dopant is preferred, and examples thereof include heterocyclic compounds, condensed aromatic compounds, etc. As the condensed aromatic compound, for example, anthracene derivatives, pyrene derivatives, chrysene derivatives, and tetracene derivatives are preferred.

[1664] As the phosphorescent host, a compound having a triplet energy level higher than that of the phosphorescent dopant is preferred, and examples thereof include metal complexes, heterocyclic compounds, condensed aromatic compounds, etc. Among them, indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc. are preferred.

[1665] (Electron Transport Layer)

[1666] The electron transport layer is a layer containing a substance with high electron transport properties. -6 cm 2 Examples of substances having an electron mobility of 100 Å / Vs or higher include metal complexes, aromatic heterocyclic compounds, aromatic hydrocarbon compounds, and polymer compounds.

[1667] Examples of the metal complex include aluminum complexes, beryllium complexes, and zinc complexes. Specifically, examples include tris(8-quinolinolate)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolate)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinolate)beryllium (abbreviation: BeBq2), bis(2-methyl-8-quinolinolate)(4-phenylphenolate)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolate)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolate]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolate]zinc(II) (abbreviation: ZnBTZ).

[1668] Examples of aromatic heterocyclic compounds include imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, and benzimidazolephenanthridine derivatives; oxazine derivatives such as pyrimidine derivatives and triazine derivatives; and compounds containing a nitrogen-containing six-membered ring structure such as quinoline derivatives, isoquinoline derivatives, and phenanthroline derivatives (including compounds having a phosphine oxide-based substituent on the heterocyclic ring). Specific examples include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), and the like.

[1669] Examples of the aromatic hydrocarbon compound include anthracene derivatives and fluoranthene derivatives.

[1670] Specific examples of the polymer compound include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), and the like.

[1671] Any substance other than these may be used for the electron transport layer as long as it is a compound with higher electron transport property than hole transport property.

[1672] The electron transport layer may be a single layer or may be a stack of two or more layers. In this case, it is preferred to arrange a layer containing a substance having a larger energy gap among substances with high electron transport properties on the side close to the light emitting layer.

[1673] The electron transport layer may include metals such as alkali metals, magnesium, alkaline earth metals, alloys containing two or more of these metals; alkali metal compounds such as 8-quinolinol lithium (abbreviated as: Liq), alkaline earth metal compounds and other metal compounds. When metals such as alkali metals, magnesium, alkaline earth metals, or alloys containing two or more of these metals are contained in the electron transport layer, their content is not particularly limited, preferably 0.1 to 50% by mass, more preferably 0.1 to 20% by mass, and further preferably 1 to 10% by mass.

[1674] When a metal compound such as an alkali metal compound or an alkaline earth metal compound is contained in the electron transport layer, its content is preferably 1 to 99% by mass, more preferably 10 to 90% by mass. In addition, when the electron transport layer is a multilayer layer, the layer located on the light emitting layer side may be formed only of these metal compounds.

[1675] (Electron Injection Layer)

[1676] The electron injection layer is a layer containing a substance with high electron injection property, and has the function of efficiently injecting electrons from the cathode to the light-emitting layer. As substances with high electron injection property, for example, alkali metals, magnesium, alkaline earth metals, and compounds thereof can be cited. Specifically, lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, lithium oxide, etc. can be cited. Other substances with electron transport properties containing alkali metals, magnesium, alkaline earth metals, or substances containing compounds thereof, such as substances containing magnesium in Alq, etc. can also be used.

[1677] In addition, a composite material including an organic compound and a donor compound may be used in the electron injection layer. Since the organic compound takes electrons from the donor compound, such a composite material has excellent electron injection and electron transport properties.

[1678] As the organic compound, a substance having excellent properties of transporting acquired electrons is preferred, and for example, the metal complexes and aromatic heterocyclic compounds described above as substances having high electron transport properties can be used.

[1679] As the compound of donor property, any substance that can supply electrons to the organic compound can be used, for example, alkali metals, magnesium, alkaline earth metals, rare earth metals, etc. can be mentioned. Specifically, lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be mentioned. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and specifically, lithium oxide, calcium oxide, barium oxide, etc. can be mentioned. In addition, Lewis bases such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[1680] (cathode)

[1681] The cathode preferably uses a metal, alloy, conductive compound, and mixture thereof with a small work function (specifically, 3.8 eV or less). Examples of cathode materials include alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (such as magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium; alloys containing rare earth metals, etc.

[1682] The cathode is usually formed by vacuum deposition or sputtering, or when silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

[1683] In addition, when the electron injection layer is provided, regardless of the size of the work function, various conductive materials such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide can be used to form the cathode. These conductive materials can be formed into a film using a sputtering method, an inkjet method, a spin coating method, etc.

[1684] (Insulation layer)

[1685] Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to the thin film. To prevent this, a thin film insulating layer can be inserted between a pair of electrodes.

[1686] Specific examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. The insulating layer may also be a mixture thereof, or may be a laminate of a plurality of layers comprising these materials.

[1687] (Spacer layer)

[1688] For example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are stacked, a spacer layer is provided between the two layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or to adjust the carrier balance. The spacer layer may also be provided between multiple phosphorescent light-emitting layers.

[1689] The spacer layer is provided between the plurality of light-emitting layers and is therefore preferably formed of a material having both electron-transporting properties and hole-transporting properties. In addition, from the viewpoint of preventing diffusion of triplet energy in adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or more.

[1690] As the substance used for the spacer layer, the same substances as those used for the hole transport layer are exemplified.

[1691] (Electron blocking layer, hole blocking layer, exciton blocking layer)

[1692] An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer.

[1693] The electron blocking layer refers to a layer having the function of blocking electrons from leaking from the light-emitting layer to the hole transport layer. The hole blocking layer refers to a layer having the function of preventing holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer is a layer having the function of blocking the excitons generated in the light-emitting layer from diffusing to the adjacent layer and confining the excitons in the light-emitting layer.

[1694] (Middle layer)

[1695] In the tandem organic EL element, an intermediate layer may be provided.

[1696] (Layer Formation Method)

[1697] The formation method of each layer of the organic EL element is not particularly limited as long as it is not recorded separately. As the formation method, known methods such as dry film-forming method and wet film-forming method can be used. As a specific example of the dry film-forming method, vacuum evaporation method, sputtering method, plasma method, ion plating method, etc. can be cited. As a specific example of the wet film-forming method, various coating methods such as spin coating, immersion method, casting method, inkjet method can be cited.

[1698] (film thickness)

[1699] The film thickness of each layer of the organic EL element is not particularly limited unless otherwise described. If the film thickness is too small, defects such as pinholes are easily generated, and sufficient luminous brightness cannot be obtained. On the other hand, if the film thickness is too large, a high driving voltage is required, and the efficiency is reduced. From this viewpoint, the film thickness is usually preferably 1nm~10μm, more preferably 1nm~0.2μm.

[1700] [Electronic equipment]

[1701] An electronic device according to one embodiment of the present invention includes an organic EL element according to one embodiment of the present invention. Specific examples of electronic devices include display components such as organic EL panel modules; display devices such as televisions, mobile phones, smart phones, and personal computers; and light-emitting devices for lighting and vehicle lamps. Example

[1702] Next, the present invention will be described in further detail with reference to Examples and Comparative Examples, but the present invention is not limited at all to the contents of these Examples.

[1703] <Compound>

[1704] The following is a list of compounds (host materials) having a deuterium atom and represented by formula (1) used in the production of organic EL devices in the following examples.

[1705] [Chemistry 184]

[1706]

[1707] The following is a list of compounds (host materials) having no deuterium atom and used in the production of organic EL devices according to the following comparative examples.

[1708] [Chemistry 185]

[1709]

[1710] Dopant materials used in the production of organic EL devices in the following Examples and Comparative Examples are shown below.

[1711] [Chemistry 186]

[1712]

[1713] Other compounds used in the production of the organic EL devices of the following Examples and Comparative Examples are shown below.

[1714] [Chemistry 187]

[1715]

[1716] <Production of organic EL elements>

[1717] Example 1-1

[1718] A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Diomatique Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was 130 nm.

[1719] The washed glass substrate with transparent electrode was placed on a substrate holder of a vacuum deposition device, and compound HI-1 was first deposited on the surface of the transparent electrode so as to cover the transparent electrode, thereby forming a HI-1 film with a thickness of 5 nm. The HI-1 film functions as a hole injection layer.

[1720] Compound HT-1 was then deposited on the HI-1 film to form an HT-1 film with a thickness of 80 nm on the HI-1 film. The HT-1 film functioned as a hole transport layer (first hole transport layer).

[1721] Compound HT-2 was then deposited on the HT-1 film to form a 10 nm thick HT-2 film on the HT-1 film. The HT-2 film functioned as an electron blocking layer (second hole transport layer).

[1722] Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the HT-2 film so that the proportion of compound BD-1 was 4% by mass, forming a BH-1:BD-1 film with a film thickness of 25 nm. This BH-1:BD-1 film functioned as a light-emitting layer.

[1723] Compound ET-1 was deposited on the light-emitting layer to form a 10 nm thick ET-1 film, which functioned as a hole barrier layer.

[1724] Compound ET-2 was evaporated on the ET-1 film to form an ET-2 film with a thickness of 15 nm. The ET-2 film functioned as an electron transport layer. LiF was evaporated on the ET-2 film to form a LiF film with a thickness of 1 nm. Metal Al was evaporated on the LiF film to form a metal cathode with a thickness of 80 nm, thereby manufacturing an organic EL element.

[1725] The layer structure of the obtained organic EL device is as follows.

[1726] ITO(130) / HI-1(5) / HT-1(80) / HT-2(10) / BH-1:BD-1(25:4 mass%) / ET-1(10) / ET-2(15) / LiF(1) / Al(80)

[1727] The numbers in brackets indicate the film thickness (unit: nm).

[1728] (Evaluation of organic EL elements)

[1729] At a current density of 50 mA / cm 2 Voltage was applied to the obtained organic EL element in a manner of , and the time (LT95 (unit: hour)) when the relative initial luminance reached 95% was measured. The results are shown in Table 1.

[1730] Examples 1-2 to 1-9 and Comparative Examples 1-1 to 1-2

[1731] The results are shown in Table 1. An organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the host materials listed in Table 1 were used as host materials for the light-emitting layer.

[1732]

[1733] From the results in Table 1, it can be seen that the organic EL elements of Examples 1-1 to 1-9 using compounds BH-1 to BH-9 having deuterium atoms as the main material of the light-emitting layer have significantly improved element life compared with the organic EL elements of Comparative Examples 1-1 and 1-2 using compounds Comp BH-1 or Comp BH-2 not having deuterium atoms.

[1734] In addition, by comparing Examples 1-1 and 1-9 with Comparative Example 1-1, and Examples 1-4 and 1-7 with Comparative Example 1-2, which use compounds with the same chemical structure but differ only in whether they contain deuterium atoms and use the same dopant material, it can be seen that the component life is greatly improved by using compounds containing deuterium atoms as the main material.

[1735] Examples 2-1 to 2-9 and Comparative Examples 2-1 to 2-2

[1736] The results are shown in Table 2, except that the compound BD-2 was used as the dopant material of the light-emitting layer and the compounds shown in Table 2 were used as the host materials.

[1737]

[1738] From the results in Table 2, it can be seen that when BD-2 is used as the dopant material, the organic EL elements of Examples 2-1 to 2-9 using compounds BH-1 to 1-9 having deuterium atoms as the main material have improved element life compared with the organic EL elements of Comparative Examples 2-1 and 2-2 using compounds Comp BH-1 and Comp BH-2 not having deuterium atoms as their respective main materials.

[1739] Examples 3-1 to 3-9 and Comparative Examples 3-1 to 3-2

[1740] The organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-3 was used as the dopant material of the light-emitting layer and the compounds shown in Table 3 were used as the host materials.

[1741]

[1742] Examples 4-1 to 4-9 and Comparative Examples 4-1 to 4-2

[1743] The organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-4 was used as the dopant material of the light-emitting layer and the compounds shown in Table 4 were used as the host materials.

[1744]

[1745] Examples 5-1 to 5-9 and Comparative Examples 5-1 to 5-2

[1746] The results are shown in Table 5, except that the compound BD-5 was used as the dopant material of the light-emitting layer and the compounds shown in Table 5 were used as the host materials, respectively, in the same manner as in Example 1-1 to prepare an organic EL device and perform evaluation.

[1747]

[1748] Examples 6-1 to 6-9 and Comparative Examples 6-1 to 6-2

[1749] An organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-6 was used as a dopant material for the light-emitting layer and the compounds shown in Table 6 were used as host materials.

[1750]

[1751] Examples 7-1 to 7-9 and Comparative Examples 7-1 to 7-2

[1752] The organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-7 was used as the dopant material of the light-emitting layer and the compounds shown in Table 7 were used as the host materials.

[1753]

[1754] Examples 8-1 to 8-9 and Comparative Examples 8-1 to 8-2

[1755] The organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-8 was used as the dopant material of the light-emitting layer and the compounds shown in Table 8 were used as the host material.

[1756]

[1757] Examples 9-1 to 9-9 and Comparative Examples 9-1 to 9-2

[1758] An organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-9 was used as a dopant material for the light-emitting layer and the compounds shown in Table 9 were used as host materials.

[1759]

[1760] Examples 10-1 to 10-9 and Comparative Examples 10-1 to 10-2

[1761] An organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-10 was used as a dopant material for the light-emitting layer and the compounds shown in Table 10 were used as host materials.

[1762]

[1763] Examples 11-1 to 11-9 and Comparative Examples 11-1 to 11-2

[1764] An organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-11 was used as a dopant material for the light-emitting layer and the compounds shown in Table 11 were used as host materials.

[1765]

[1766] Examples 12-1 to 12-9 and Comparative Examples 12-1 to 12-2

[1767] The organic EL device was prepared and evaluated in the same manner as in Example 1-1 except that the compound BD-12 was used as the dopant material of the light-emitting layer and the compounds shown in Table 12 were used as the host materials.

[1768]

[1769] The results of Tables 3 to 12 also confirm the same tendency as Tables 1 and 2. That is, it can be seen that even if the dopant material used is changed, the organic EL elements of the examples using the host material compounds BH-1 to BH-9 having deuterium atoms have a significantly improved device life compared to the organic EL elements of the comparative examples using the host material compounds CompBH-1 or Comp BH-2 not having deuterium atoms.

[1770] Furthermore, when comparing the examples and comparative examples using host material compounds having the same chemical structure but differing only in whether or not they contain deuterium atoms, and using the same dopant material, it can be seen that the device life is significantly improved by using compounds containing deuterium atoms.

[1771] Synthesis Example 1 [Synthesis of Compound BH-1]

[1772] The synthetic route of BH-1 is shown below.

[1773] [Chemistry 188]

[1774]

[1775] (1-1) Synthesis of BH-1-1

[1776] Under argon atmosphere, 75 mL of toluene, 75 mL of dimethoxyethane (DME) and 75 mL of 2M Na2CO3 aqueous solution were added to 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 6.4 g (52.5 mmol) of phenylboronic acid and 41.2 g (1.00 mmol) of Pd[PPh3], and the mixture was heated and stirred at about 80°C for 10 hours.

[1777] After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.9 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as BH-1-1 (yield 83%).

[1778] (1-2) Synthesis of BH-1-2

[1779] A solution prepared by dissolving 5.3 g (20.0 mmol) of BH-1-1 in 120 mL of dichloromethane was added dropwise to a solution prepared by dissolving 3.6 g (20.0 mmol) of N-bromosuccinimide (NBS) in 15 mL of dichloromethane at room temperature, followed by stirring for 1 hour.

[1780] After the reaction was completed, the reaction solution was transferred to a separatory funnel and washed with a 2M Na2S2O3 aqueous solution. The organic phase was further washed with 10% Na2CO3 and then with water, and the separated organic phase was dried over MgSO4, filtered, and concentrated.

[1781] The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were collected by filtration to obtain 6.5 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-1-2 (yield 95%).

[1782] (1-3) Synthesis of BH-1

[1783] Under argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.7 g (5.0 mmol) of BH-1-2, 1.4 g (5.2 mmol) of triphenylene-5-boric acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1784] After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-1 (yield 70%).

[1785] Synthesis Example 2 [Synthesis of Compound BH-2]

[1786] The synthetic route of BH-2 is shown below.

[1787] [Chemistry 189]

[1788]

[1789] (2-1) Synthesis of BH-2-1

[1790] Under argon atmosphere, 75 mL of toluene, 75 mL of dimethoxyethane and 75 mL of 2M Na2CO3 aqueous solution were added to 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 9.0 g (52.5 mmol) of 2-naphthylboronic acid and 41.2 g (1.00 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1791] After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 12.5 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as BH-2-1 (yield 80%).

[1792] (2-2) Synthesis of BH-2-2

[1793] A solution prepared by dissolving 5.3 g (20.0 mmol) of BH-2-1 in 120 mL of dichloromethane was added dropwise to a solution prepared by dissolving 3.0 g (20.0 mmol) of N-bromosuccinimide (NBS) in 10 mL of dichloromethane at room temperature, followed by stirring for 1 hour.

[1794] After the reaction was completed, the reaction solution was transferred to a separatory funnel and washed with a 2M Na2S2O3 aqueous solution. The organic phase was further washed with 10% Na2CO3 and then with water, and the separated organic phase was dried over MgSO4, filtered, and concentrated.

[1795] The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were collected by filtration to obtain 5.8 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-2-2 (yield 88%).

[1796] (2-3) Synthesis of BH-2

[1797] Under argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.7 g (5.0 mmol) of BH-2-2, 1.4 g (5.2 mmol) of triphenylene-5-boric acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1798] After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.5 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-2 (yield 66%).

[1799] Synthesis Example 3 [Synthesis of Compound BH-3]

[1800] The synthetic route of BH-3 is shown below.

[1801] [Chemistry 190]

[1802]

[1803] (3-1) Synthesis of BH-3-1

[1804] Under argon atmosphere, 75 mL of toluene, 75 mL of dimethoxyethane and 90 mL of 2M Na2CO3 aqueous solution were added to 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of biphenylboronic acid and 41.2 g (1.00 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1805] After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 13.6 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as BH-3-1 (yield 80%).

[1806] (3-2) Synthesis of BH-3-2

[1807] A solution prepared by dissolving 5.3 g (15.6 mmol) of BH-3-1 in 120 mL of dichloromethane was added dropwise to a solution prepared by dissolving 2.8 g (15.6 mmol) of N-bromosuccinimide (NBS) in 10 mL of dichloromethane at room temperature, followed by stirring for 1 hour.

[1808] After the reaction was completed, the reaction solution was transferred to a separatory funnel and washed with a 2M Na2S2O3 aqueous solution. The organic phase was further washed with 10% Na2CO3 and then with water, and the separated organic phase was dried over MgSO4, filtered, and concentrated.

[1809] The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were collected by filtration to obtain 5.9 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-3-2 (yield 90%).

[1810] (3-3) Synthesis of BH-3

[1811] Under an argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.5 g (3.6 mmol) of BH-3-2, 1.0 g (3.8 mmol) of triphenylene-5-boric acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was heated and stirred at about 80°C for 10 hours.

[1812] After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried with MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.4 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-3 (yield 70%).

[1813] Synthesis Example 4 [Synthesis of Compound BH-4]

[1814] The synthetic route of BH-4 is shown below.

[1815] [Chemistry 191]

[1816]

[1817] (4-1) Synthesis of BH-4

[1818] Under argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.5 g (3.6 mmol) of BH-1-2, 1.0 g (3.8 mmol) of benzanthracene-4-boric acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was heated and stirred at about 80°C for 10 hours.

[1819] After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.2 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-4 (yield 60%).

[1820] Synthesis Example 5 [Synthesis of Compound BH-5]

[1821] The synthetic route of BH-5 is shown below.

[1822] [Chemistry 192]

[1823]

[1824] (5-1) Synthesis of BH-5-1

[1825] Under argon atmosphere, 75 mL of toluene, 75 mL of dimethoxyethane and 75 mL of 2M Na2CO3 aqueous solution were added to 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 9.0 g (52.5 mmol) of 1-naphthylboronic acid and 41.2 g (1.00 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1826] After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 12.5 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as BH-5-1 (yield 80%).

[1827] (5-2) Synthesis of BH-5-2

[1828] A solution prepared by dissolving 5.0 g (20.0 mmol) of BH-5-1 in 120 mL of dichloromethane was added dropwise to a solution prepared by dissolving 2.8 g (20.0 mmol) of N-bromosuccinimide (NBS) in 10 mL of dichloromethane at room temperature, followed by stirring for 1 hour.

[1829] After the reaction was completed, the reaction solution was transferred to a separatory funnel and washed with a 2M Na2S2O3 aqueous solution. The organic phase was further washed with 10% Na2CO3 and then with water, and the separated organic phase was dried over MgSO4, filtered, and concentrated.

[1830] The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were collected by filtration to obtain 5.5 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-5-2 (yield 88%).

[1831] (5-3) Synthesis of BH-5

[1832] Under argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.5 g (3.8 mmol) of BH-5-2, 1.1 g (4.0 mmol) of benzanthracene-4-boric acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was heated and stirred at about 80°C for 10 hours.

[1833] After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.1 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-5 (yield 55%).

[1834] Synthesis Example 6 [Synthesis of Compound BH-6]

[1835] The synthetic route of BH-6 is shown below.

[1836] [Chemistry 193]

[1837]

[1838] (6-1) Synthesis of BH-6

[1839] Under an argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.5 g (3.6 mmol) of BH-1-2, 1.6 g (4.6 mmol) of 3-(7-benzanthracene)phenylboronic acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was heated and stirred at about 80°C for 10 hours.

[1840] After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried with MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.9 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-6 (yield 75%).

[1841] Synthesis Example 7 [Synthesis of Compound BH-7]

[1842] The synthetic route of BH-7 is shown below.

[1843] [Chemistry 194]

[1844]

[1845] (7-1) Synthesis of BH-7-1

[1846] Under argon atmosphere, 75 mL of toluene, 75 mL of dimethoxyethane and 75 mL of 2M Na2CO3 aqueous solution were added to 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 6.7 g (52.5 mmol) of phenylboronic acid-d5 and 41.6 g (1.00 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1847] After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.7 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-7-1 (yield 80%).

[1848] (7-2) Synthesis of BH-7-2

[1849] A solution prepared by dissolving 5.0 g (18.6 mmol) of BH-7-1 in 120 mL of dichloromethane was added dropwise to a solution prepared by dissolving 3.3 g (18.6 mmol) of N-bromosuccinimide (NBS) in 12 mL of dichloromethane at room temperature, followed by stirring for 1 hour.

[1850] After the reaction was completed, the reaction solution was transferred to a separatory funnel and washed with a 2M Na2S2O3 aqueous solution. The organic phase was further washed with 10% Na2CO3 and then with water, and the separated organic phase was dried over MgSO4, filtered, and concentrated.

[1851] The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were collected by filtration to obtain 5.8 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-7-2 (yield 90%).

[1852] (7-3) Synthesis of BH-7

[1853] Under an argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.7 g (5.0 mmol) of BH-7-2, 1.4 g (5.3 mmol) of benzanthracene-4-boric acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was heated and stirred at about 80°C for 10 hours.

[1854] After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as BH-7 (yield 70%).

[1855] Synthesis Example 8 [Synthesis of Compound BH-8]

[1856] The synthetic route of BH-8 is shown below.

[1857] [Chemistry 195]

[1858]

[1859] (8-1) Synthesis of BH-8

[1860] Under argon atmosphere, 7.5 mL of toluene, 7.5 mL of dimethoxyethane and 7.5 mL of 2M Na2CO3 aqueous solution were added to 1.7 g (5.0 mmol) of BH-1-2, 1.7 g (5.3 mmol) of benzochrysene-6-boric acid and 40.1 g (0.1 mmol) of Pd[PPh3], and the mixture was heated and stirred at about 80°C for 10 hours.

[1861] After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.6 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as BH-8 (yield 60%).

[1862] Synthesis Example 9 [Synthesis of Compound BH-9]

[1863] The synthetic route of BH-9 is shown below.

[1864] [Chemistry 196]

[1865]

[1866] (9-1) Synthesis of BH-9-1

[1867] Under argon atmosphere, 75 mL of toluene, 75 mL of dimethoxyethane and 75 mL of 2M Na2CO3 aqueous solution were added to 15.0 g (56.4 mmol) of 9-bromoanthracene-d9, 10.7 g (85.0 mmol) of phenylboronic acid-d5 and 41.3 g (1.13 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1868] After the reaction was completed, the mixture was cooled to room temperature, the sample was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 12.1 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-9-1 (yield 80%).

[1869] (9-2) Synthesis of BH-9-2

[1870] A solution obtained by dissolving 10.0 g (37.3 mmol) of BH-9-1 in 240 mL of dichloromethane was added dropwise to a solution obtained by dissolving 6.6 g (37.3 mmol) of N-bromosuccinimide (NBS) in 30 mL of dichloromethane at room temperature, followed by stirring for 1 hour.

[1871] After the reaction was completed, the sample was transferred to a separatory funnel and washed with a 2M Na2S2O3 aqueous solution. The organic phase was further washed with 10% Na2CO3 and then with water, and the separated organic phase was dried over MgSO4, filtered, and concentrated.

[1872] The concentrated residue was dispersed in methanol (200 mL) and the collected crystals were filtered to obtain 7.7 g of a white solid. The obtained compound was analyzed by FD-MS and identified as BH-9-2 (yield 60%).

[1873] (9-3) Synthesis of BH-9

[1874] Under an argon atmosphere, 15 mL of toluene, 15 mL of dimethoxyethane and 15 mL of 2M Na2CO3 aqueous solution were added to 5.0 g (14.4 mmol) of BH-9-2, 4.1 g (14.4 mmol) of triphenylene-5-boronic acid-d11 and 40.3 g (0.3 mmol) of Pd[PPh3], and the mixture was stirred with heating at about 80°C for 10 hours.

[1875] After the reaction was completed, the mixture was cooled to room temperature, the sample was transferred to a separatory funnel and extracted with dichloromethane. The organic phase was dried over MgSO4, filtered, and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 4.0 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-9 (yield 55%).

[1876] Several embodiments and / or examples of the present invention are described in detail above, and those skilled in the art can easily make more changes to these illustrative embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, these more changes are also included in the scope of the present invention. The documents recorded in this specification and the contents of the applications that serve as the basis for the priority of the Paris Convention based on this application are all cited.

Claims

1. A compound represented by the following formula (1-1), In formula (1-1), R1 to R8 are deuterium atoms, (L1) m11 and (L2) m12 Each is independently a single bond, Unsubstituted phenylene, Unsubstituted biphenylene, or unsubstituted naphthylene, Ar 1A is an unsubstituted phenyl group, unsubstituted naphthyl, or Unsubstituted Fiki, Ar 2B is an unsubstituted monovalent group derived from the following polycyclic condensed aromatic hydrocarbons, Triphenylene, Benzene (a) anthracene, Triphenylene, and Benzotriphenylene, Selected from (L1) m11 、(L2) m12 ,Ar 1A and Ar 2B One or more of the hydrogen atoms contained in one or more groups in may be deuterium atoms.

2. The compound according to claim 1, wherein The compound represented by the aforementioned formula (1-1) is a compound represented by the following formula (1-2), In formula (1-2), R1 to R8, (L2) m12 ,Ar 1A and Ar 2B As defined in the above formula (1-1).

3. The compound according to claim 1, wherein The compound represented by the aforementioned formula (1-1) is a compound represented by the following formula (1-3), In formula (1-3), R1 to R8, (L1) m11 ,Ar 1A and Ar 2B As defined in the above formula (1-1).

4. The compound according to claim 1, wherein (L1) m11 and (L2) m12 Each independently is a single bond, Unsubstituted phenylene, or Unsubstituted biphenylene.

5. The compound according to claim 1, wherein Ar 2B is an unsubstituted monovalent group derived from a polycyclic condensed aromatic hydrocarbon selected from the following formulae (b1) to (b4), 6. The compound according to claim 5, wherein Ar 2B It is an unsubstituted monovalent group derived from a polycyclic condensed aromatic hydrocarbon selected from the group consisting of the above formulae (b2) to (b4).

7. The compound according to claim 5, wherein Ar 2B It is an unsubstituted monovalent group derived from the polycyclic condensed aromatic hydrocarbon represented by the above formula (b2).

8. The compound according to claim 5, wherein Ar 2B It is an unsubstituted monovalent group derived from the polycyclic condensed aromatic hydrocarbon represented by the above formula (b3).

9. The compound according to claim 5, wherein Ar 2B It is an unsubstituted monovalent group derived from the polycyclic condensed aromatic hydrocarbon represented by the above formula (b4).

10. The compound according to claim 1, wherein Selected from (L1) m11 、(L2) m12 ,Ar 1A and Ar 2B At least one of the hydrogen atoms in at least one group in is a deuterium atom.

11. The compound according to claim 1, wherein Ar 1A One or more of the hydrogen atoms present is a deuterium atom.

12. The compound according to claim 1, wherein (L1) m11 、(L2) m12 ,Ar 1A and Ar 2B All hydrogen atoms are protium atoms.

13. The compound according to claim 1, which is selected from the compounds shown below, wherein: D represents deuterium atom, 14. The compound according to claim 1, which is selected from the following (BH-1) to (BH-9), wherein: D represents deuterium atom, 15 . A material for an organic electroluminescent device, comprising the compound according to claim 1 .

16. A composition comprising the compound described in any one of claims 1 to 14, wherein the content ratio of the compound represented by the aforementioned formula (1-1) and the compound having the same structure as the compound represented by the aforementioned formula (1-1) except that it contains only protium atoms as hydrogen atoms is 99 mol% or less.

17. An organic electroluminescent element having a cathode, Anode, and a light-emitting layer disposed between the cathode and the anode, The light-emitting layer comprises the compound according to any one of claims 1 to 14 and a dopant material, The dopant material is one or more compounds selected from the group consisting of a compound represented by the following formula (17), a compound represented by the following formula (33), and a compound represented by the following formula (43). In formula (17), R 111 ~R 118 , R 121 ~R 127 and R 131 ~R 135 Each independently Hydrogen atoms, Unsubstituted methyl, Unsubstituted ethyl, Unsubstituted n-propyl, Unsubstituted isopropyl, Unsubstituted tert-butyl, Unsubstituted cyclohexyl, Unsubstituted phenyl, or unsubstituted naphthyl, In formula (33), R 351 and R 352 are each independently a hydrogen atom, or Unsubstituted phenyl, R 361 ~R 364 Each independently Unsubstituted phenyl, Phenyl substituted by unsubstituted methyl, Phenyl substituted with unsubstituted ethyl, Phenyl substituted with unsubstituted n-propyl, Phenyl substituted with unsubstituted isopropyl, Phenyl substituted with unsubstituted tert-butyl, Phenyl substituted by unsubstituted cyclohexyl, Phenyl substituted by unsubstituted phenyl, or Phenyl substituted by unsubstituted naphthyl, In formula (43), R 431 ~R 451 In one or more groups of two or more adjacent groups, the two or more adjacent groups are bonded to each other and do not form an unsubstituted saturated or unsaturated ring. R 431 ~R 451 Each independently Hydrogen atoms, Unsubstituted methyl, Unsubstituted ethyl, Unsubstituted n-propyl, Unsubstituted isopropyl, Unsubstituted tert-butyl, Unsubstituted cyclohexyl, Unsubstituted phenyl, unsubstituted naphthyl, or -N(R 906 )(R 907 ), R 906 and R 907 It is an unsubstituted phenyl group.

18. The organic electroluminescent element according to claim 17, wherein The dopant material is a compound represented by the above formula (17).

19. The organic electroluminescent element according to claim 17, wherein: The aforementioned dopant material is a compound represented by the aforementioned formula (33).

20. The organic electroluminescent element according to claim 17, wherein The aforementioned dopant material is a compound represented by the aforementioned formula (43).

21. The organic electroluminescent element according to claim 17, wherein A hole transport layer is provided between the anode and the light emitting layer.

22. The organic electroluminescent element according to claim 17, wherein: An electron transport layer is provided between the cathode and the light emitting layer.

23. An electronic device comprising the organic electroluminescent element according to any one of claims 17 to 22.

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