Organic electroluminescent element and electronic device

Abstract

An organic electroluminescent element having an anode, a cathode, and a light-emitting region located between the anode and the cathode; the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer and the second light-emitting layer are directly adjacent to each other, the first light-emitting layer is located between the anode and the second light-emitting layer, and either the first light-emitting layer or the second light-emitting layer contains a compound having at least one deuterium atom.

Description

Technical Field

[0001] The present invention relates to an organic electroluminescent element and an electronic device. Background Art

[0002] When a voltage is applied to an organic electroluminescent element (hereinafter referred to as an organic EL element), holes are injected from an anode and electrons are injected from a cathode into a light-emitting layer. Subsequently, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] The organic EL element includes a light-emitting layer between an anode and a cathode. In addition, it sometimes has a stacked structure including organic layers such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.

[0004] Patent Documents 1 to 4 disclose deuterated arylanthracene compounds that can be used for electronic applications, and electronic devices in which an active layer contains such deuterium compounds.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: WO2010 / 099534

[0008] Patent Document 2: WO2010 / 135395

[0009] Patent Document 3: WO2011 / 028216

[0010] Patent Document 4: WO2010 / 071362. Summary of the Invention

[0011] An object of the present invention is to provide a long-life organic electroluminescent element and an electronic device using a deuterated compound.

[0012] According to one aspect of the present invention, the following organic electroluminescent element is provided.

[0013] An organic electroluminescent element having:

[0014] An anode,

[0015] A cathode, and

[0016] A light-emitting region located between the aforementioned anode and the aforementioned cathode,

[0017] The aforementioned light-emitting region includes a first light-emitting layer and a second light-emitting layer,

[0018] The aforementioned first light-emitting layer and the aforementioned second light-emitting layer are directly adjacent,

[0019] The aforementioned first light-emitting layer is located between the aforementioned anode and the aforementioned second light-emitting layer,

[0020] Either the aforementioned first light-emitting layer or the aforementioned second light-emitting layer contains a compound having at least one deuterium atom.

[0021] According to another method of the present invention, there is provided an electronic device having the above-described organic electroluminescent element.

[0022] According to the present invention, by using a deuterated compound, an organic electroluminescent element and an electronic device with a long lifespan can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 : A diagram showing a schematic configuration of an organic EL element according to a first aspect of the present invention.

[0024] Figure 2 : A diagram showing a schematic configuration of an organic EL element according to a second aspect of the present invention.

[0025] Figure 3 : A diagram showing a schematic configuration of an organic EL element according to a third aspect of the present invention. DETAILED DESCRIPTION

[0026] [Definition]

[0027] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely, protium, deuterium, and tritium.

[0028] In this specification, in a chemical structural formula, at a bondable position where symbols such as "R" and "D" representing deuterium atoms are not explicitly shown, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded.

[0029] In this specification, the number of ring-forming carbon atoms refers to the number of carbon atoms among the atoms constituting the ring itself of a compound in which atoms are bonded in a ring shape (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbon atoms. The same applies to the "number of ring-forming carbon atoms" described below. For example, the number of ring-forming carbon atoms of a benzene ring is 6, the number of ring-forming carbon atoms of a naphthalene ring is 10, the number of ring-forming carbon atoms of a pyridine ring is 5, and the number of ring-forming carbon atoms of a furan ring is 4. Additionally, for example, the number of ring-forming carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring-forming carbon atoms of 9,9'-spirobifluorenyl is 25.

[0030] In addition, when an alkyl group, for example, is substituted on a benzene ring or a naphthalene ring as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms.

[0031] In this specification, the number of ring-forming atoms refers to the number of atoms that form a ring structure (such as a monocyclic, fused-ring, or ring assembly) in a compound (such as a monocyclic compound, fused-ring compound, crosslinked compound, carbocyclic compound, or heterocyclic compound). Atoms that do not form a ring (such as hydrogen atoms that cap the bonds of the atoms forming the ring) and atoms contained in substituents when the ring is substituted are not included in the number of ring-forming atoms. The same applies to the "number of ring-forming atoms" described below. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. Hydrogen atoms bonded to the carbon atoms of the pyridine ring and quinazoline ring respectively and atoms forming substituents are not included in the number of ring-forming atoms.

[0032] In this specification, in the expression "ZZ group having XX to YY carbon atoms, which may be substituted or unsubstituted", "XX to YY carbon atoms" refers to the number of carbon atoms in the ZZ group when it is unsubstituted, and does not include the carbon atoms of the substituent when it is substituted. Here, "YY" is greater than "XX", and "XX" and "YY" each refer to an integer of 1 or more.

[0033] In this specification, in the expression "ZZ group having XX to YY atoms, which may be substituted or unsubstituted", "XX to YY atoms" refers to the number of atoms in the ZZ group when it is unsubstituted, and does not include the atoms of the substituent when it is substituted. Here, "YY" is greater than "XX", and "XX" and "YY" each refer to an integer of 1 or more.

[0034] In the case of "ZZ group, which may be substituted or unsubstituted", "unsubstituted" means that the ZZ group is not substituted by a substituent and is bonded to a hydrogen atom. Alternatively, in the case of "ZZ group, which may be substituted or unsubstituted", "substituted" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. In the case of "BB group substituted by AA group", "substituted" also means that one or more hydrogen atoms in the BB group are replaced by the AA group.

[0035] Hereinafter, the substituents described in this specification will be described.

[0036] Unless otherwise specified in this specification, the number of ring-forming carbon atoms in the "unsubstituted aryl" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0037] Unless otherwise specified in this specification, the number of ring-forming atoms in the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0038] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkyl" described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0039] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkenyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6.

[0040] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkynyl" described in this specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6.

[0041] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted cycloalkyl" described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6.

[0042] Unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted arylene" described in this specification is 6 to 50, preferably 6 to 30, more preferably 6 to 18.

[0043] Unless otherwise specified in this specification, the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18.

[0044] Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkylene" described in this specification is 1 to 50, preferably 1 to 20, more preferably 1 to 6.

[0045] As specific examples (specific example group G1) of the "substituted or unsubstituted aryl" described in this specification, the following unsubstituted aryls, substituted aryls, etc. can be cited. (In this text, the unsubstituted aryl means the case where the "substituted or unsubstituted aryl" is an "unsubstituted aryl", and the substituted aryl means the case where the "substituted or unsubstituted aryl" is a "substituted aryl".) Hereinafter, when simply referring to "aryl", it includes both "unsubstituted aryl" and "substituted aryl".

[0046] "Substituted aryl" is the case where the "unsubstituted aryl" has a substituent, and groups in which the following "unsubstituted aryl" has a substituent, examples of substituted aryls, etc. can be cited. It should be noted that the examples of the "unsubstituted aryl" and the examples of the "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the group in which the "unsubstituted aryl" has a substituent further has a substituent, groups in which the "substituted aryl" further has a substituent, etc.

[0047] Unsubstituted aryl:

[0048] Phenyl,

[0049] Biphenyl,

[0050] m - Biphenyl,

[0051] o - Terphenyl

[0052] p - Terphenyl - 4 - yl

[0053] p - Terphenyl - 3 - yl

[0054] p - Terphenyl - 2 - yl

[0055] m - Terphenyl - 4 - yl

[0056] m - Terphenyl - 3 - yl

[0057] m - Terphenyl - 2 - yl

[0058] o - Terphenyl - 4 - yl

[0059] o - Terphenyl - 3 - yl

[0060] o - Terphenyl - 2 - yl

[0061] 1 - Naphthyl

[0062] 2 - Naphthyl

[0063] Anthracenyl

[0064] Benzo[a]anthracenyl

[0065] Phenanthrenyl

[0066] Benzo[a]phenanthrenyl

[0067] Phenalenyl

[0068] Pyrenyl

[0069] Chrysenyl

[0070] Benzo[c]chrysenyl

[0071] Triphenylenyl

[0072] Benzo[e]triphenylenyl

[0073] Tetracenyl

[0074] Pentacenyl

[0075] Fluorenyl

[0076] 9,9’ - Spirobifluorenyl

[0077] Benzo[b]fluorenyl

[0078] Dibenzo[a,c]fluorenyl

[0079] Fluoranthenyl

[0080] Benzo[j]fluoranthenyl

[0081] Perylenyl

[0082] Substituted aryl:

[0083] o-Tolyl,

[0084] m-Tolyl,

[0085] p-Tolyl,

[0086] p-Xylyl,

[0087] m-Xylyl,

[0088] o-Xylyl,

[0089] p-Isopropylphenyl,

[0090] m-Isopropylphenyl,

[0091] o-Isopropylphenyl,

[0092] p-tert-Butylphenyl,

[0093] m-tert-Butylphenyl,

[0094] o-tert-Butylphenyl,

[0095] 3,4,5-Trimethylphenyl,

[0096] 9,9-Dimethylfluorenyl,

[0097] 9,9-Diphenylfluorenyl,

[0098] 9,9-Bis(4-methylphenyl)fluorenyl,

[0099] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0100] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0101] Cyanophenyl,

[0102] Triphenylsilylphenyl,

[0103] Trimethylsilylphenyl,

[0104] Phenylnaphthyl,

[0105] Naphthylphenyl.

[0106] The "heterocyclic group" described in this specification is a cyclic group containing at least 1 heteroatom in the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

[0107] The "heterocyclic group" described in this specification may be a monocyclic group or a fused-ring group.

[0108] The "heterocyclic group" described in this specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.

[0109] As specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification, the following unsubstituted heterocyclic groups and substituted heterocyclic groups can be cited. (In this text, 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 simply referring to the "heterocyclic group", it includes both the "unsubstituted heterocyclic group" and the "substituted heterocyclic group".

[0110] The "substituted heterocyclic group" is the case where the "unsubstituted heterocyclic group" has a substituent, and groups in which the following "unsubstituted heterocyclic groups" have substituents, examples of substituted heterocyclic groups, etc. can be cited. It should be noted that the examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification also includes groups in which the group in which the "unsubstituted heterocyclic group" has a substituent further has a substituent, groups in which the "substituted heterocyclic group" further has a substituent, etc.

[0111] Unsubstituted heterocyclic groups containing a nitrogen atom:

[0112] Pyrrolyl,

[0113] Imidazolyl,

[0114] Pyrazolyl,

[0115] Triazolyl,

[0116] Tetrazolyl,

[0117] Oxazolyl,

[0118] Isoxazolyl,

[0119] Oxadiazolyl,

[0120] Thiazolyl,

[0121] Isothiazolyl,

[0122] Thiadiazolyl,

[0123] Pyridyl,

[0124] Pyridazinyl,

[0125] Pyrimidinyl,

[0126] Pyrazinyl,

[0127] Triazinyl,

[0128] Indolyl,

[0129] isoindolyl,

[0130] indolizinyl,

[0131] quinolizinyl,

[0132] quinolyl,

[0133] isoquinolyl,

[0134] cinnolinyl,

[0135] phthalazinyl,

[0136] quinazolinyl,

[0137] quinoxalinyl,

[0138] benzimidazolyl,

[0139] indazolyl,

[0140] phenanthrolinyl,

[0141] phenanthridinyl,

[0142] acridinyl,

[0143] phenoxazinyl,

[0144] carbazolyl,

[0145] benzocarbazolyl,

[0146] morpholinyl,

[0147] phenoxazinyl,

[0148] phenothiazinyl,

[0149] azacarbazolyl,

[0150] diazacarbazolyl.

[0151] Unsubstituted heterocyclic groups containing an oxygen atom:

[0152] furyl,

[0153] oxazolyl,

[0154] isoxazolyl,

[0155] oxadiazolyl,

[0156] xanthenyl,

[0157] benzofuryl,

[0158] isobenzofuryl,

[0159] dibenzofuryl,

[0160] naphthobenzofuryl,

[0161] Benzoxazolyl,

[0162] Benzisoxazolyl,

[0163] Phenoxazinyl,

[0164] Morpholinyl,

[0165] Dinaphthofuranyl,

[0166] Aza-dibenzofuranyl,

[0167] Diaza-dibenzofuranyl,

[0168] Aza-naphthobenzofuranyl,

[0169] Diaza-naphthobenzofuranyl.

[0170] Unsubstituted heterocyclic groups containing a sulfur atom:

[0171] Thienyl,

[0172] Thiazolyl,

[0173] Isothiazolyl,

[0174] Thiadiazolyl,

[0175] Benzothienyl,

[0176] Isobenzothienyl,

[0177] Dibenzothienyl,

[0178] Naphthobenzothienyl,

[0179] Benzothiazolyl,

[0180] Benzisothiazolyl,

[0181] Phenothiazinyl,

[0182] Dinaphthothienyl,

[0183] Aza-dibenzothienyl,

[0184] Diaza-dibenzothienyl,

[0185] Aza-naphthobenzothienyl,

[0186] Diaza-naphthobenzothienyl.

[0187] Substituted heterocyclic groups containing a nitrogen atom:

[0188] (9-Phenyl)carbazolyl,

[0189] (9-Biphenyl)carbazolyl,

[0190] (9-Phenyl)phenylcarbazolyl,

[0191] (9-naphthyl)carbazolyl,

[0192] Diphenylcarbazole-9-yl,

[0193] Phenylcarbazol-9-yl,

[0194] Methylbenzimidazolyl,

[0195] Ethylbenzimidazolyl,

[0196] Phenyl triazine,

[0197] Biphenyl triazine,

[0198] Diphenyltriazine,

[0199] Phenylquinazolinyl,

[0200] Biphenylquinazolinyl.

[0201] Substituted heterocyclic groups containing oxygen atoms:

[0202] Phenyldibenzofuranyl,

[0203] Methyldibenzofuranyl,

[0204] tert-Butyldibenzofuranyl,

[0205] A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0206] Substituted heterocyclic groups containing a sulfur atom:

[0207] Phenyldibenzothiophene,

[0208] Methyldibenzothiophene,

[0209] tert-Butyldibenzothienyl,

[0210] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0211] 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:

[0212] [Chemistry 1]

[0213]

[0214] In formulas (XY-1) to (XY-18), X A and Y AEach independently represents an oxygen atom, a sulfur atom, NH, or CH 2 . Among them, X A and Y A at least one of which is an oxygen atom, a sulfur atom, or NH.

[0215] The heterocycles represented by the above formulas (XY-1) to (XY-18) have a bond at any position to form a monovalent heterocyclic group.

[0216] When a monovalent group derived from an unsubstituted heterocycle represented by the above formulas (XY-1) to (XY-18) has a substituent, it means that a hydrogen atom bonded to a carbon atom constituting the skeleton in these formulas is replaced by a substituent, or X A , Y A is NH or CH 2 , and the hydrogen atom in these NH or CH 2 is replaced by a substituent.

[0217] As specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification, the following unsubstituted alkyl groups and substituted alkyl groups can be cited. (In this article, an unsubstituted alkyl group means the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and a substituted alkyl group means the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when simply referring to an "alkyl group", it includes both an "unsubstituted alkyl group" and a "substituted alkyl group".

[0218] A "substituted alkyl group" is a case where an "unsubstituted alkyl group" has a substituent, and examples thereof include groups in which the following "unsubstituted alkyl group" has a substituent, examples of substituted alkyl groups, etc. It should be noted that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are only examples, and the "substituted alkyl group" described in this specification also includes groups in which a group in which the "unsubstituted alkyl group" has a substituent further has a substituent, groups in which the "substituted alkyl group" further has a substituent, etc.

[0219] Unsubstituted alkyl group:

[0220] Methyl,

[0221] Ethyl,

[0222] n-Propyl,

[0223] Isopropyl,

[0224] n-Butyl,

[0225] Isobutyl,

[0226] sec-Butyl,

[0227] tert-Butyl.

[0228] Substituted alkyl:

[0229] Heptafluoropropyl (including isomers),

[0230] Pentafluoroethyl,

[0231] 2,2,2-Trifluoroethyl,

[0232] Trifluoromethyl.

[0233] As specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl" described in this specification, the following unsubstituted alkenyl and substituted alkenyl, etc. can be cited. (In this article, the unsubstituted alkenyl refers to the case where the "substituted or unsubstituted alkenyl" is an "unsubstituted alkenyl", and the "substituted alkenyl" refers to the case where the "substituted or unsubstituted alkenyl" is a "substituted alkenyl".) Hereinafter, when simply referring to "alkenyl", it includes both "unsubstituted alkenyl" and "substituted alkenyl".

[0234] The "substituted alkenyl" is the case where the "unsubstituted alkenyl" has a substituent, and groups in which the following "unsubstituted alkenyl" has a substituent, examples of substituted alkenyl, etc. can be cited. It should be noted that the examples of the "unsubstituted alkenyl" and the examples of the "substituted alkenyl" listed here are only one example, and the "substituted alkenyl" described in this specification also includes groups in which the group in which the "unsubstituted alkenyl" has a substituent further has a substituent, groups in which the "substituted alkenyl" further has a substituent, etc.

[0235] Unsubstituted alkenyl and substituted alkenyl:

[0236] Vinyl,

[0237] Allyl,

[0238] 1-Butenyl,

[0239] 2-Butenyl,

[0240] 3-Butenyl,

[0241] 1,3-Butadienyl,

[0242] 1-Methylvinyl,

[0243] 1-Methylallyl,

[0244] 1,1-Dimethylallyl,

[0245] 2-Methylallyl,

[0246] 1,2-Dimethylallyl.

[0247] As a specific example (specific example group G5) of the "substituted or unsubstituted alkynyl" described in this specification, the following unsubstituted alkynyls and the like can be cited. (In this text, the unsubstituted alkynyl means the case where the "substituted or unsubstituted alkynyl" is an "unsubstituted alkynyl".) Hereinafter, when simply referring to "alkynyl", it includes both "unsubstituted alkynyl" and "substituted alkynyl".

[0248] "Substituted alkynyl" is the case where the "unsubstituted alkynyl" has a substituent, and groups in which the following "unsubstituted alkynyl" has a substituent and the like can be cited.

[0249] Unsubstituted alkynyl:

[0250] Ethynyl.

[0251] As a specific example (specific example group G6) of the "substituted or unsubstituted cycloalkyl" described in this specification, the following unsubstituted cycloalkyls and substituted cycloalkyls and the like can be cited. (In this text, the unsubstituted cycloalkyl means the case where the "substituted or unsubstituted cycloalkyl" is an "unsubstituted cycloalkyl", and the substituted cycloalkyl means the case where the "substituted or unsubstituted cycloalkyl" is a "substituted cycloalkyl".) Hereinafter, when simply referring to "cycloalkyl", it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0252] "Substituted cycloalkyl" is the case where the "unsubstituted cycloalkyl" has a substituent, and groups in which the following "unsubstituted cycloalkyl" has a substituent, examples of substituted cycloalkyls, and the like can be cited. It should be noted that the examples of the "unsubstituted cycloalkyl" and the examples of the "substituted cycloalkyl" listed here are only one example, and the "substituted cycloalkyl" described in this specification also includes groups in which the group in which the "unsubstituted cycloalkyl" has a substituent further has a substituent, groups in which the "substituted cycloalkyl" further has a substituent, and the like.

[0253] Unsubstituted aliphatic ring group:

[0254] Cyclopropyl,

[0255] Cyclobutyl,

[0256] Cyclopentyl,

[0257] Cyclohexyl,

[0258] 1-Adamantyl,

[0259] 2-Adamantyl,

[0260] 1-Norbornyl,

[0261] 2-Norbornyl.

[0262] Substituted cycloalkyl:

[0263] 4-Methylcyclohexyl.

[0264] As a specific example (specific example group G7) of the group represented by -Si(R 901 )(R 902 )(R 903 ) described in this specification, the following can be cited:

[0265] -Si(G1)(G1)(G1),

[0266] -Si(G1)(G2)(G2),

[0267] -Si(G1)(G1)(G2),

[0268] -Si(G2)(G2)(G2),

[0269] -Si(G3)(G3)(G3),

[0270] -Si(G5)(G5)(G5),

[0271] -Si(G6)(G6)(G6).

[0272] In this text,

[0273] G1 is the "aryl group" described in specific example group G1.

[0274] G2 is the "heterocyclic group" described in specific example group G2.

[0275] G3 is the "alkyl group" described in specific example group G3.

[0276] G5 is the "alkynyl group" described in specific example group G5.

[0277] G6 is the "cycloalkyl group" described in specific example group G6.

[0278] As a specific example (specific example group G8) of the group represented by -O-(R 904 ) described in this specification, the following can be cited:

[0279] -O(G1),

[0280] -O(G2),

[0281] -O(G3),

[0282] -O(G6).

[0283] In this text,

[0284] G1 is the "aryl group" described in specific example group G1.

[0285] G2 is the "heterocyclic group" described in specific example group G2.

[0286] G3 is the "alkyl group" described in specific example group G3.

[0287] G6 is the "cycloalkyl group" described in specific example group G6.

[0288] As specific examples (specific example group G9) of the group represented by -S-(R 905 ), the following can be cited:

[0289] -S(G1),

[0290] -S(G2),

[0291] -S(G3),

[0292] -S(G6).

[0293] In this text,

[0294] G1 is the "aryl group" described in specific example group G1.

[0295] G2 is the "heterocyclic group" described in specific example group G2.

[0296] G3 is the "alkyl group" described in specific example group G3.

[0297] G6 is the "cycloalkyl group" described in specific example group G6.

[0298] As specific examples (specific example group G10) of the group represented by -N(R 906 )(R 907 ), the following can be cited:

[0299] -N(G1)(G1),

[0300] -N(G2)(G2),

[0301] -N(G1)(G2),

[0302] -N(G3)(G3),

[0303] -N(G6)(G6).

[0304] In this text,

[0305] G1 is the "aryl group" described in specific example group G1.

[0306] G2 is the "heterocyclic group" described in specific example group G2.

[0307] G3 is the "alkyl group" described in specific example group G3.

[0308] G6 is the "cycloalkyl group" described in specific example group G6.

[0309] As specific examples (specific example group G11) of the "halogen atom" described in this specification, fluorine atom, chlorine atom, bromine atom, iodine atom, etc. can be cited.

[0310] A specific example of the "alkoxy group" described in this specification is a group represented by -O(G3), where G3 is the "alkyl group" described in specific example group G3. In this text, unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0311] A specific example of the "alkylthio group" described in this specification is a group represented by -S(G3), where G3 is the "alkyl group" described in specific example group G3. In this text, unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0312] A specific example of the "aryloxy group" described in this specification is a group represented by -O(G1), where G1 is the "aryl group" described in specific example group G1. In this text, unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0313] A specific example of the "arylthio group" described in this specification is a group represented by -S(G1), where G1 is the "aryl group" described in specific example group G1. In this text, unless otherwise specified in this specification, the number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0314] A specific example of the "aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is the "alkyl group" described in specific example group G3 and G1 is the "aryl group" described in specific example group G1. Therefore, the "aralkyl group" is an embodiment of the "substituted alkyl group" substituted by the "aryl group". In this text, unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted alkyl group" substituted by the "unsubstituted aryl group", that is, the "unsubstituted aralkyl group", is 7 to 50, preferably 7 to 30, and more preferably 7 to 18.

[0315] As specific examples of the "aralkyl group", for example, 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, 2-β-naphthylisopropyl, etc. can be cited.

[0316] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described in this specification are preferably phenyl, p-biphenylyl, m-biphenylyl, o-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-diphenylfluorenyl, etc.

[0317] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described in this specification are preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, phenyldibenzothiophenyl, indolocarbazolyl, pyrazinyl, pyridazinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, pyrrolo[3,2,1-jk]carbazolyl, furyl, benzofuranyl, thienyl, benzothienyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, thiadiazolyl, isoxazolyl, benzisoxazolyl, pyrrolidinyl, piperidinyl, piperazinyl, imidazolidinyl, indolol[3,2,1-jk]carbazolyl, dibenzothiophenyl, etc.

[0318] Unless otherwise specified in this specification, the above dibenzofuranyl and dibenzothiophenyl are specifically any of the following groups.

[0319] [Chemical formula 2]

[0320]

[0321] In formulas (XY-76) to (XY-79), X B is an oxygen atom or a sulfur atom.

[0322] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described in this specification are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.

[0323] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification refers to a divalent group obtained by changing the above-mentioned "aryl group" to a divalent group. As specific examples (specific example group G12) of the "substituted or unsubstituted arylene group", groups obtained by removing one hydrogen atom bonded to the ring-forming carbon in the "aryl group" described in specific example group G1 can be cited, etc. That is, as specific examples (specific example group G12) of the "substituted or unsubstituted arylene group", groups obtained by removing one hydrogen atom bonded to the ring-forming carbon in the "aryl group" described in specific example group G1 can be cited.

[0324] As specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group" described in this specification, groups obtained by changing the "heterocyclic group" described in specific example group G2 to a divalent group can be cited, etc. That is, as specific examples (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", groups obtained by removing one hydrogen atom bonded to the ring-forming atom in the "heterocyclic group" described in specific example group G2 can be cited.

[0325] As specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group" described in this specification, groups obtained by changing the "alkyl group" described in specific example group G3 to a divalent group can be cited, etc. That is, as specific examples (specific example group G14) of the "substituted or unsubstituted alkylene group", groups obtained by removing one hydrogen atom bonded to the carbon forming the alkane structure in the "alkyl group" described in specific example group G3 can be cited.

[0326] Unless otherwise specified in this specification, the substituted or unsubstituted arylene groups described in this specification are preferably any of the following groups.

[0327] [Chemical formula 3]

[0328]

[0329] In formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R 908 is a substituent.

[0330] m901 is an integer from 0 to 4. When m901 is 2 or more, multiple Rs present 908 may be the same or different from each other.

[0331] [Chemical formula 4]

[0332]

[0333] In formulas (XY-30) to (XY-40), R909 Each independently represents a hydrogen atom or a substituent. Two Rs 909 may be bonded to each other via a single bond to form a ring.

[0334] [Chemical formula 5]

[0335]

[0336] In formulas (XY-41) to (XY-46), R 910 is a substituent.

[0337] m902 is an integer from 0 to 6. When m902 is 2 or more, multiple existing Rs 910 may be the same or different from each other.

[0338] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any of the following groups.

[0339] [Chemical formula 6]

[0340]

[0341] In formulas (XY-50) to (XY-60), R 911 is a hydrogen atom or a substituent.

[0342] [Chemical formula 7]

[0343]

[0344] In the above formulas (XY-65) to (XY-75), X B is an oxygen atom or a sulfur atom.

[0345] In this specification, for the case of "two or more adjacent groups bonding to each other to form a substituted or unsubstituted saturated or unsaturated ring", the case of an anthracene compound represented by the following formula (XY-80) having an anthracene ring as the parent skeleton is taken as an example for explanation.

[0346] [Chemical formula 8]

[0347]

[0348] For example, as R 921 to R 930 in the case of "two or more adjacent groups bonding to each other to form a ring", two adjacent ones of one group refer to R 921 and R 922 , R 922 and R 923 , R 923 and R 924 , R 924 and R930 , R 930 and R 925 , R 925 and R 926 , R 926 and R 927 , R 927 and R 928 , R 928 and R 929 , and R 929 and R 921 .

[0349] The above "more than 1 set" means that more than 2 sets of the above adjacent 2 can form a ring simultaneously. For example, R 921 and R 922 bond with each other to form ring A, and at the same time R 925 and R 926 bond with each other to form ring B, and the situation is represented by the following formula (XY - 81).

[0350] [Chemical formula 9]

[0351]

[0352] The situation where "more than 2 adjacent" form a ring. For example, R 921 and R 922 bond with each other to form ring A, R 922 and R 923 bond with each other to form ring C, and a situation where 3 mutually adjacent ones from R 921 to R 923 are fused into an anthracene parent skeleton and share R 922 of ring A and ring C is represented by the following formula (XY - 82).

[0353] [Chemical formula 10]

[0354]

[0355] The rings A - C formed in the above formulas (XY - 81) and (XY - 82) are saturated or unsaturated rings.

[0356] "Unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. "Saturated ring" means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.

[0357] For example, the ring A formed by the bonding of R 921 and R 922 shown in the above formula (XY - 81) means a ring formed by the carbon atoms of the anthracene skeleton bonded by R 921 and the carbon atoms of the anthracene skeleton bonded by R 922 and one or more arbitrary elements. As a specific example, in the case of R 921 and R922 In the case of forming ring A, R 921 The carbon atom of the bonded anthracene skeleton, R 922 When the carbon atom of the bonded anthracene skeleton forms an unsaturated ring with 4 carbon atoms, the ring formed by R 921 and R 922 becomes a benzene ring. In addition, when a saturated ring is formed, it becomes a cyclohexane ring.

[0358] In this text, "any element" is preferably a C element, an N element, an O element, or an S element. Among any elements (for example, in the case of a C element or an N element), the bond not involved in forming a ring can be capped with a hydrogen atom or the like, or can be substituted with any substituent. When any element other than the C element is contained, the formed ring becomes a heterocyclic ring.

[0359] "One or more arbitrary elements" constituting a saturated or unsaturated ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less.

[0360] As a specific example of an aromatic hydrocarbon ring, a structure in which an aryl listed as a specific example in specific example group G1 is capped with a hydrogen atom can be cited.

[0361] As a specific example of an aromatic heterocyclic ring, a structure in which an aromatic heterocyclic group listed as a specific example in specific example group G2 is capped with a hydrogen atom can be cited.

[0362] As a specific example of an aliphatic hydrocarbon ring, a structure in which a cycloalkyl listed as a specific example in specific example group G6 is capped with a hydrogen atom can be cited.

[0363] When the above-mentioned "saturated or unsaturated ring" has a substituent, the substituent is, for example, the following "any substituent". Specific examples of the substituent when the above-mentioned "saturated or unsaturated ring" has a substituent are the substituents described in the item of "substituents described in this specification" above.

[0364] In one embodiment of this specification, the substituent in the case of the aforementioned "substituted or unsubstituted" (hereinafter, sometimes referred to as "any substituent") is selected from the following groups:

[0365] An unsubstituted alkyl group having 1 to 50 carbon atoms,

[0366] An unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0367] An unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0368] An unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0369] -Si(R 901 )(R902 )(R 903 ),

[0370] -O-(R 904 ),

[0371] -S-(R 905 ),

[0372] -N(R 906 )(R 907 )

[0373] (In this text,

[0374] R 901 ~R 907 are each independently:

[0375] A hydrogen atom,

[0376] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0377] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0378] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0379] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When there are two or more of R 901 ~R 907 Two or more R 901 ~R 907 can be the same or different from each other.)、

[0380] A halogen atom, a cyano group, a nitro group,

[0381] An unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0382] An unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0383] In one embodiment, the substituent in the case of the aforementioned "substituted or unsubstituted" is selected from the following groups:

[0384] An alkyl group having 1 to 50 carbon atoms,

[0385] An aryl group having 6 to 50 ring carbon atoms, and

[0386] A monovalent heterocyclic group having 5 to 50 ring atoms.

[0387] In one embodiment, the substituent in the case of the aforementioned "substituted or unsubstituted" is selected from the following groups:

[0388] An alkyl group having 1 to 18 carbon atoms,

[0389] an aryl group having 6 to 18 ring carbon atoms, and

[0390] a monovalent heterocyclic group having 5 to 18 ring atoms.

[0391] Specific examples of each group of any of the above substituents are as described above.

[0392] 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 or 6-membered ring, more preferably a benzene ring).

[0393] In the present specification, unless otherwise specified, any substituent may further have a substituent. Examples of the substituent that any substituent further has include the same substituents as any of the above substituents.

[0394] [Organic electroluminescent element]

[0395] The organic electroluminescent element according to the first aspect of the present invention has:

[0396] an anode,

[0397] a cathode, and

[0398] a light-emitting region located between the anode and the cathode,

[0399] the light-emitting region includes a first light-emitting layer and a second light-emitting layer,

[0400] the first light-emitting layer and the second light-emitting layer are directly adjacent to each other,

[0401] the first light-emitting layer is located between the anode and the second light-emitting layer,

[0402] either the first light-emitting layer or the second light-emitting layer includes a compound having at least one deuterium atom.

[0403] Refer to Figure 1 to illustrate the schematic configuration of the organic EL element according to the first aspect of the present invention.

[0404] An organic EL element 1A according to one aspect of the present invention has a substrate 2, an anode 3, a cathode 4, and an organic layer 10 between the anode 3 and the cathode 4. The organic layer 10 has a light-emitting region 5, an organic thin film layer 6 located between the anode 3 and the light-emitting region 5, and an organic thin film layer 7 located between the light-emitting region 5 and the cathode 4.

[0405] The light-emitting region 5 includes a first light-emitting layer 5A on the anode side and a second light-emitting layer 5B on the cathode side, and the first light-emitting layer 5A is adjacent to the second light-emitting layer.

[0406] Either the first light-emitting layer 5A or the second light-emitting layer 5B contains a compound having at least one deuterium atom.

[0407] The inventors have found that by having a light-emitting layer in the light-emitting region, the light-emitting layer contains a compound having a deuterium atom, whereby the lifetime of the organic EL element is improved.

[0408] In one embodiment, only either the first light-emitting layer or the second light-emitting layer contains a compound having at least one deuterium atom, and the other substantially does not contain a compound having a deuterium atom.

[0409] As used herein, "substantially does not contain a compound having a deuterium atom" means that it completely does not contain deuterium atoms, or allows the inclusion of deuterium atoms at the natural abundance level. The natural abundance of deuterium atoms is, for example, 0.015% or less.

[0410] That is, as used herein, "contains a compound having at least one deuterium atom" means that the light-emitting layer contains a compound having a deuterium atom in an amount exceeding the natural abundance.

[0411] The inclusion of deuterium atoms in a compound can be confirmed by mass spectrometry or 1 1H-NMR analysis. In addition, the bonding position of the deuterium atoms in the compound is identified by 1 1H-NMR analysis. Specifically, as described below.

[0412] Perform mass spectrometry on the target compound and compare it with the corresponding compound in which all hydrogen atoms are protium atoms. If the molecular weight increases by 1, it can be confirmed that one deuterium atom is contained. In addition, since deuterium atoms do not appear as signals in 1 1H-NMR analysis, the number of deuterium atoms contained in the molecule can be confirmed based on the integral value obtained by performing 1 1H-NMR analysis on the target compound. In addition, perform 1 1H-NMR analysis on the target compound and assign the signals, whereby the bonding position of the deuterium atoms can be identified.

[0413] The ratio of the film thickness (film thickness T1) of the light-emitting layer containing a compound having a deuterium atom to the film thickness (film thickness T2) of the light-emitting layer not containing a compound having a deuterium atom is, for example, 0.05 < (T1 / (T1 + T2)) < 0.9. From the viewpoint of avoiding excessive use of a compound having a deuterium atom (cost viewpoint), the ratio of the film thickness (film thickness T1) of the light-emitting layer containing a compound having a deuterium atom to the film thickness (film thickness T2) of the light-emitting layer not containing a compound having a deuterium atom is 0.05 < (T1 / (T1 + T2)) < 0.7, preferably 0.05 < (T1 / (T1 + T2)) < 0.6, more preferably 0.1 < (T1 / (T1 + T2)) < 0.5, for example 0.1 < (T1 / (T1 + T2)) < 0.4. From the viewpoint of achieving a long lifetime, the ratio of the film thickness (film thickness T1) of the light-emitting layer containing a compound having a deuterium atom to the film thickness (film thickness T2) of the light-emitting layer not containing a compound having a deuterium atom is preferably 0.1 ≤ (T1 / (T1 + T2)), more preferably 0.3 ≤ (T1 / (T1 + T2)). Further, it is also preferably (T1 / (T1 + T2)) ≤ 0.9. Considering both lifetime and cost, it is preferably 0.2 ≤ (T1 / (T1 + T2)) ≤ 0.7, more preferably 0.2 ≤ (T1 / (T1 + T2)) ≤ 0.5.

[0414] In one embodiment, the ratio of the film thickness (film thickness T1) of the first light-emitting layer to the film thickness (film thickness T2) of the second light-emitting layer is, for example, 0.05 < (T1 / (T1 + T2)) < 0.9. The ratio of the film thickness (film thickness T1) of the first light-emitting layer to the film thickness (film thickness T2) of the second light-emitting layer is preferably 0.05 < (T1 / (T1 + T2)) < 0.6, more preferably 0.1 < (T1 / (T1 + T2)) < 0.5, for example 0.1 < (T1 / (T1 + T2)) < 0.4.

[0415] From the viewpoint of lifetime, the film thickness (film thickness T1) of the light-emitting layer containing a compound having a deuterium atom is preferably 2.5 nm or more, more preferably 7.5 nm or more. Further, it is also preferably 22.5 nm or less. On the other hand, from the viewpoint of avoiding excessive use of a compound having a deuterium atom (cost viewpoint), the smaller the film thickness (film thickness T1) of the light-emitting layer containing a compound having a deuterium atom, the more preferable, and it is preferably 17.5 nm or less. More preferably, the film thickness T1 is 12.5 nm or less. Even more preferably, the film thickness T1 is 10 nm or less. Considering both lifetime and cost, the film thickness T1 is preferably 5 nm or more and 17.5 nm or less, and the film thickness T1 is more preferably 5 nm or more and 12.5 nm or less.

[0416] In one embodiment, the aforementioned first light-emitting layer and the aforementioned second light-emitting layer each independently contain a host material and a dopant material. The dopant material is preferably a blue light-emitting dopant.

[0417] A compound having at least one deuterium atom can be a host material or a dopant material.

[0418] In one embodiment, the aforementioned compound having at least one deuterium atom is the aforementioned host material.

[0419] Relative to the whole light-emitting layer, the content of the host material in the light-emitting layer is preferably 80% by mass or more and 99% by mass or less.

[0420] Relative to the whole light-emitting layer, the content of the dopant material in the light-emitting layer is preferably 1% by mass or more and 20% by mass or less.

[0421] The number of deuterium atoms of the compound having at least one deuterium atom is preferably 1 to 100, more preferably 1 to 80.

[0422] In the case where the compound having at least one deuterium atom is a dopant material, the number of deuterium atoms is preferably 1 to 100, more preferably 1 to 80.

[0423] In the case where the compound having at least one deuterium atom is a host material, the number of deuterium atoms is preferably 1 to 50, more preferably 1 to 40.

[0424] In one embodiment, the aforementioned compound having at least one deuterium atom is the aforementioned host material, and the aforementioned host material is a compound having at least one of an anthracene skeleton, a pyrene skeleton, a chrysene skeleton, and a fluorene skeleton.

[0425] In one embodiment, the aforementioned compound having at least one deuterium atom is the aforementioned host material, and the aforementioned host material is a compound having an anthracene skeleton. At least one deuterium atom can be any one of the hydrogen atoms constituting the compound having an anthracene skeleton.

[0426] In one embodiment, the aforementioned compound having at least one deuterium atom is the aforementioned host material, and the aforementioned host material is a compound having an anthracene skeleton, and at least one of the hydrogen atoms bonded to the carbon atoms on the anthracene skeleton is a deuterium atom.

[0427] In other embodiments, the aforementioned compound having at least one deuterium atom is the aforementioned host material, and the aforementioned host material is a compound having an anthracene skeleton, and at least one of the hydrogen atoms bonded to the carbon atoms other than the carbon atoms on the anthracene skeleton is a deuterium atom. The carbon atoms other than the carbon atoms on the anthracene skeleton refer to the carbon atoms constituting the so-called side chain structure.

[0428] In addition, the aforementioned at least one deuterium atom can be bonded to both the carbon atoms on the anthracene skeleton and the carbon atoms other than the carbon atoms on the anthracene skeleton.

[0429] In one embodiment, the aforementioned first light-emitting layer contains a compound having at least one deuterium atom.

[0430] In one embodiment, the first light-emitting layer contains only a compound having at least one deuterium atom as a host material.

[0431] When there are two light-emitting layers in the light-emitting region, the first light-emitting layer on the anode side preferably contains a compound having at least one deuterium atom. The compound having at least one deuterium atom can be one or both of the host material and the dopant material.

[0432] In one embodiment, the aforementioned first light-emitting layer contains a compound having at least one deuterium atom,

[0433] The aforementioned second light-emitting layer contains a compound having an anthracene skeleton, a pyrene skeleton, a chrysene skeleton, or a fluorene skeleton.

[0434] At this time, the material of the second light-emitting layer is preferably a compound having an anthracene skeleton, a pyrene skeleton, a chrysene skeleton, or a fluorene skeleton that does not contain a deuterium atom.

[0435] In one embodiment, when the deuterium atoms of the host material of the aforementioned first light-emitting layer are replaced with protium atoms, the chemical structure is the same as that of the host material of the aforementioned second light-emitting layer.

[0436] In one embodiment, the dopant material of the aforementioned first light-emitting layer is the same as the dopant material of the aforementioned second light-emitting layer.

[0437] In one embodiment, at least one of the aforementioned first light-emitting layer and the aforementioned second light-emitting layer is a light-emitting layer containing one or two or more host materials.

[0438] When the light-emitting layer containing two or more host materials contains a deuterium atom-containing host material, only one of them can be a compound having a deuterium atom, and the other can be a compound without a deuterium atom, or both can be deuterium atom-containing compounds.

[0439] In one embodiment, the aforementioned first light-emitting layer does not contain a metal complex.

[0440] In one embodiment, the aforementioned second light-emitting layer does not contain a metal complex.

[0441] As a specific example of the "metal complex", a phosphorescent metal complex such as an iridium complex can be cited. The "phosphorescent metal complex" functions as a phosphorescent dopant material.

[0442] In one embodiment, the first light-emitting layer and / or the second light-emitting layer does not contain a phosphorescent dopant material. At this time, the first light-emitting layer and / or the second light-emitting layer becomes a light-emitting layer that emits fluorescence.

[0443] In one embodiment, the first light-emitting layer and / or the second light-emitting layer does not contain a phosphorescent metal complex.

[0444] In one embodiment, the first light-emitting layer and / or the second light-emitting layer does not contain an iridium complex.

[0445] Specific examples of the dopant material for the organic EL element suitable for one mode of the present invention will be described later.

[0446] In the organic EL element of the second mode of the present invention, the light-emitting region further has a third light-emitting layer,

[0447] the second light-emitting layer is directly adjacent to the third light-emitting layer,

[0448] the third light-emitting layer is located between the cathode and the second light-emitting layer.

[0449] In one embodiment, the light-emitting region further has a third light-emitting layer,

[0450] the second light-emitting layer is directly adjacent to the third light-emitting layer,

[0451] the third light-emitting layer is located between the cathode and the second light-emitting layer,

[0452] the second light-emitting layer contains a compound having at least one deuterium atom.

[0453] Refer to Figure 2 The schematic configuration of the organic EL element of the second mode of the present invention will be described.

[0454] Figure 2 The organic EL element 1B of the second mode of the present invention shown in has: a substrate 2, an anode 3, a cathode 4, and an organic layer 10 between the anode 3 and the cathode 4. The organic layer 10 has a light-emitting region 5, a hole injection / transport layer 6 located between the anode 3 and the light-emitting region 5, and an electron injection / transport layer 7 located between the light-emitting region 5 and the cathode 4.

[0455] The light-emitting region 5 includes a first light-emitting layer 5A on the anode side and a second light-emitting layer 5B on the cathode side, and the first light-emitting layer 5A is adjacent to the second light-emitting layer.

[0456] Either the first light-emitting layer 5A or the second light-emitting layer 5B contains a compound having at least one deuterium atom.

[0457] The light-emitting region 5 includes a third light-emitting layer 5C on the cathode side of the second light-emitting layer 5B, and the third light-emitting layer 5C is adjacent to the second light-emitting layer 5B.

[0458] The second light-emitting layer 5B contains a compound having at least one deuterium atom.

[0459] In the light-emitting region 5 of the organic EL element 1B according to the second aspect of the present invention described above, there are a first, a second, and a third light-emitting layer (5A, 5B, 5C) adjacent to each other, and the second light-emitting layer (5B) is sandwiched by the other two light-emitting layers (5A, 5C) adjacent to the second light-emitting layer (5B). The second light-emitting layer (5B) contains a material having at least one deuterium atom. By having such a structure in the light-emitting region 5, a compound having at least one deuterium atom can be disposed in a region not adjacent to peripheral layers such as a hole transport layer and an electron transport layer. As a result, even when deterioration occurs at the interface between these peripheral layers and an adjacent layer (i.e., the light-emitting layers (5A, 5C)), it is possible to expect an effect of preventing deterioration in the layer (i.e., the light-emitting layer (5B)) containing the compound having at least one deuterium atom.

[0460] The organic EL element according to the third aspect of the present invention further has a third light-emitting layer and a fourth light-emitting layer between the second light-emitting layer and the cathode described above.

[0461] The third light-emitting layer and the fourth light-emitting layer are directly adjacent to each other.

[0462] The fourth light-emitting layer is provided between the third light-emitting layer and the cathode.

[0463] Either the third light-emitting layer or the fourth light-emitting layer contains a compound having at least one deuterium atom.

[0464] In one embodiment of the organic EL element according to the third aspect of the present invention, a third light-emitting layer and a fourth light-emitting layer are further provided.

[0465] The third light-emitting layer and the fourth light-emitting layer are directly adjacent to each other.

[0466] The fourth light-emitting layer is provided between the third light-emitting layer and the cathode.

[0467] Either the third light-emitting layer or the fourth light-emitting layer contains a compound having at least one deuterium atom.

[0468] A charge generation layer is provided between the second light-emitting layer and the third light-emitting layer.

[0469] Refer to Figure 3 The schematic configuration of the organic EL element according to the third aspect of the present invention will be described.

[0470] Figure 3The organic EL element 1C of the third embodiment of the present invention shown in [description] has: a substrate 2, an anode 3, a cathode 4, and an organic layer 10 between the anode 3 and the cathode 4. The organic layer 10 has a light-emitting region 5, a hole injection / transport layer 6 located between the anode 3 and the light-emitting region 5, and an electron injection / transport layer 7 located between the light-emitting region 5 and the cathode 4.

[0471] The light-emitting region 5 includes a first light-emitting layer 5A on the anode side and a second light-emitting layer 5B on the cathode side, and the first light-emitting layer 5A is adjacent to the second light-emitting layer.

[0472] The light-emitting region 5 further includes a third light-emitting layer 5C and a fourth light-emitting layer 5D, and the fourth light-emitting layer 5D is on the cathode 4 side of the third light-emitting layer 5C. The third light-emitting layer 5C and the fourth light-emitting layer 5D are adjacent. The first light-emitting layer 5A and the second light-emitting layer 5B, and the third light-emitting layer 5C and the fourth light-emitting layer 5D may both be on the cathode 4 side. Figure 3 The case where the third light-emitting layer 5C and the fourth light-emitting layer 5D are on the cathode 4 side is shown in [description].

[0473] Either the first light-emitting layer 5A or the second light-emitting layer 5B contains a material having at least one deuterium atom, and either the third light-emitting layer 5C or the fourth light-emitting layer 5D contains a compound having at least one deuterium atom.

[0474] Figure 3 In one embodiment of the third embodiment of the present invention shown in [description], the organic EL element 1C further has a charge generation layer 9 between the second light-emitting layer 5B and the third light-emitting layer 5C.

[0475] In the light-emitting region 5 of the organic EL element 1C of the third embodiment of the present invention described above, there are a first and a second light-emitting layers (5A, 5B) adjacent to each other, and a third and a fourth light-emitting layers (5C, 5D) adjacent to each other. Either the first and the second light-emitting layers (5A, 5B) or the third and the fourth light-emitting layers (5C, 5D) contain a compound having at least one deuterium atom. It has a so-called tandem type configuration in which two sets of stacked light-emitting layers are provided. By having such a tandem type structure in the light-emitting region 5, effects of high brightness and long life can be expected. In addition, a white light-emitting element with a simple structure can be manufactured.

[0476] In one embodiment, the host material having at least one deuterium atom is a compound represented by the following formula (1).

[0477] [Chemical formula 11]

[0478]

[0479] In formula (1),

[0480] R 1~R 8 Each independently is:

[0481] a hydrogen atom,

[0482] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0483] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0484] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0485] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0486] -Si(R 901 )(R 902 )(R 903 ),

[0487] -O-(R 904 ),

[0488] -S-(R 905 ),

[0489] -N(R 906 )(R 907 ),

[0490] a halogen atom, a cyano group, a nitro group,

[0491] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0492] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0493] R 901 ~R 907 Each independently is:

[0494] a hydrogen atom,

[0495] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0496] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0497] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0498] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0499] R 901 ~R 907 When there are two or more, two or more of R 901 ~R 907 may be the same or different from each other.

[0500] R 1 ~R 4 Two or more adjacent ones among them, and R 5 ~R 8 Two or more adjacent ones among them do not bond to each other to form a ring.

[0501] L 1 and L 2 Each independently is:

[0502] A single bond,

[0503] A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0504] A divalent heterocyclic group having 5 to 30 ring atoms which is substituted or unsubstituted.

[0505] Ar 1 and Ar 2 Each independently is:

[0506] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0507] A monovalent heterocyclic group having 5 to 50 ring atoms which is substituted or unsubstituted.

[0508] R being a hydrogen atom 1 ~R 8 、and at least one of the hydrogen atoms of one or more groups selected from R 1 ~R 8 、L not being a single bond 1 、L not being a single bond 2 、Ar 1 and Ar 2 is a deuterium atom.

[0509] The compound represented by the foregoing formula (1) has one or more deuterium atoms at any position within the molecule.

[0510] R in the foregoing formula (1) 1 ~R 8 at least one of which is a deuterium atom, or at least one of the hydrogen atoms of one or more groups selected from R 1 ~R 8 、L not being a single bond 1 、L not being a single bond 2 、Ar 1 and Ar 2 is a deuterium atom. Or, at least one of R 1 ~R 8 is a deuterium atom, and at least one of the hydrogen atoms of one or more groups selected from R 1 ~R8 and L that is not a single bond 1 and L that is not a single bond 2 Ar 1 and Ar 2 at least one hydrogen atom in one or more groups among them is a deuterium atom.

[0511] In an organic EL element according to one embodiment of the present invention, preferably, in the light-emitting layer, with respect to the total of the compound represented by formula (1) and a compound having the same structure as the compound represented by formula (1) except that it contains only protium atoms as hydrogen atoms (hereinafter, also referred to as "light hydrogen compound"), the content ratio of the latter is 99 mol% or less. The content ratio of the light hydrogen compound is confirmed by mass spectrometry.

[0512] R 1 to R 8 may all be deuterium atoms, or a part thereof (for example, 1 or 2) may be deuterium atoms.

[0513] R that is not a deuterium atom 1 to R 8 is preferably a protium atom.

[0514] A first embodiment of the compound represented by formula (1) is a compound represented by formula (1A) below.

[0515] [Chemical formula 12]

[0516]

[0517] In formula (1A),

[0518] R 1 to R 8 each independently represents:

[0519] a hydrogen atom,

[0520] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0521] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0522] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0523] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0524] -Si(R 901 )(R 902 )(R 903 ),

[0525] -O-(R 904 ),

[0526] -S-(R 905 ),

[0527] -N(R 906 )(R 907 ),

[0528] a halogen atom, a cyano group, a nitro group,

[0529] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0530] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0531] R 901 to R 907 are each independently:

[0532] a hydrogen atom,

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

[0534] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0535] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0536] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0537] R 901 to R 907 When there are two or more, two or more of R 901 to R 907 may be the same or different from each other.

[0538] At least one of R 1 to R 8 is a deuterium atom.

[0539] Two or more adjacent ones of R 1 to R 4 and two or more adjacent ones of R 5 to R 8 do not bond to each other to form a ring.

[0540] L 1A and L 2A are each independently:

[0541] a single bond,

[0542] a substituted or unsubstituted phenylene group,

[0543] a substituted or unsubstituted naphthylene group,

[0544] a substituted or unsubstituted biphenylene group,

[0545] Substituted or unsubstituted terphenyl-4,4'-diyl,

[0546] substituted or unsubstituted anthracene-2,6-diyl, or

[0547] substituted or unsubstituted phenanthrene-3,8-diyl.

[0548] Ar 1A and Ar 2A are each independently:

[0549] substituted or unsubstituted phenyl,

[0550] substituted or unsubstituted naphthyl,

[0551] substituted or unsubstituted biphenyl,

[0552] substituted or unsubstituted terphenyl,

[0553] substituted or unsubstituted anthryl, or

[0554] substituted or unsubstituted phenanthryl.

[0555] L 1A 、L 2A 、Ar 1A and Ar 2A in the case of having substituents, the substituents are:

[0556] an alkyl group having 1 to 50 carbon atoms,

[0557] an alkenyl group having 2 to 50 carbon atoms,

[0558] an alkynyl group having 2 to 50 carbon atoms,

[0559] a cycloalkyl group having 3 to 50 ring carbon atoms,

[0560] an alkylsilyl group having 1 to 50 carbon atoms,

[0561] a halogen atom, or

[0562] a cyano group.

[0563] R 1 ~R 8 may all be deuterium atoms, or a part thereof (for example, 1 or 2) may be deuterium atoms.

[0564] R that is not a deuterium atom 1 ~R 8 is preferably a hydrogen atom (protium).

[0565] In one embodiment, selected from L 1A and L 2AAt least one of the hydrogen atoms possessed by more than one of them is a deuterium atom. Specifically, in one embodiment, selected from L 1A and L 2A more than one of them is:

[0566] An unsubstituted phenylene group in which at least one of the hydrogen atoms is a deuterium atom,

[0567] An unsubstituted naphthylene group in which at least one of the hydrogen atoms is a deuterium atom,

[0568] An unsubstituted biphenylene group in which at least one of the hydrogen atoms is a deuterium atom,

[0569] An unsubstituted terphenyl group in which at least one of the hydrogen atoms is a deuterium atom,

[0570] An unsubstituted anthryl group in which at least one of the hydrogen atoms is a deuterium atom, or

[0571] An unsubstituted phenanthryl group in which at least one of the hydrogen atoms is a deuterium atom.

[0572] In one embodiment, L 1A and L 2A are each independently a single bond, a substituted or unsubstituted phenylene group, or a naphthylene group. Preferably, at least one of L 1A and L 2A is a single bond.

[0573] In one embodiment, at least one of the hydrogen atoms possessed by more than one of those selected from Ar 1A and Ar 2A is a deuterium atom. Specifically, in one embodiment, more than one of those selected from Ar 1A and Ar 2A is:

[0574] An unsubstituted phenyl group in which at least one of the hydrogen atoms is a deuterium atom,

[0575] An unsubstituted naphthyl group in which at least one of the hydrogen atoms is a deuterium atom,

[0576] An unsubstituted biphenyl group in which at least one of the hydrogen atoms is a deuterium atom,

[0577] An unsubstituted terphenyl group in which at least one of the hydrogen atoms is a deuterium atom,

[0578] An unsubstituted anthryl group in which at least one of the hydrogen atoms is a deuterium atom, or

[0579] An unsubstituted phenanthryl group in which at least one of the hydrogen atoms is a deuterium atom.

[0580] In one embodiment, Ar 1A and Ar 2AEach independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group.

[0581] For the compound represented by formula (1A), according to the synthesis method described in the examples, by using known alternative reactions and raw materials corresponding to the target, the compounds within the scope of the invention of this application can be synthesized.

[0582] As the compound represented by formula (1A), for example, the following compounds can be cited as specific examples. In the following specific examples, D represents a deuterium atom.

[0583] [Chemical formula 13]

[0584]

[0585] [Chemical formula 14]

[0586]

[0587] [Chemical formula 15]

[0588]

[0589] [Chemical formula 16]

[0590]

[0591] [Chemical formula 17]

[0592]

[0593] [Chemical formula 18]

[0594]

[0595] [Chemical formula 19]

[0596]

[0597] [Chemical formula 20]

[0598]

[0599] The second form of the compound represented by the aforementioned formula (1) is the compound represented by the following formula (1B).

[0600] [Chemical formula 21]

[0601]

[0602] In formula (1B),

[0603] R 1 ~R 8 Each independently is:

[0604] a hydrogen atom

[0605] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms

[0606] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms

[0607] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms

[0608] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms

[0609] -Si(R 901 )(R 902 )(R 903 )

[0610] -O-(R 904 )

[0611] -S-(R 905 )

[0612] -N(R 906 )(R 907 )

[0613] a halogen atom, a cyano group, a nitro group

[0614] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0615] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms

[0616] R 901 to R 907 each independently is

[0617] a hydrogen atom

[0618] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms

[0619] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms

[0620] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0621] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms

[0622] R 901 to R 907 When there are two or more, two or more R 901 to R 907 may be the same or different from each other

[0623] R1 ~R 8 At least one of them is a deuterium atom.

[0624] R 1 ~R 4 Two or more adjacent ones among R 5 ~R 8 Two or more adjacent ones do not bond to each other to form a ring.

[0625] L 1B and L 2B Each independently is:

[0626] A single bond,

[0627] A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0628] A divalent heterocyclic group having 5 to 30 ring atoms which is substituted or unsubstituted.

[0629] Ar 2B is:

[0630] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0631] A monovalent heterocyclic group having 5 to 50 ring atoms which is substituted or unsubstituted.

[0632] R 11B ~R 18B One of them is a single bond bonded to L 1B bond.

[0633] Not the R which is a single bond bonded to L 1B bond 11B ~R 18B Each independently is:

[0634] A hydrogen atom,

[0635] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0636] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0637] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0638] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0639] -Si(R 901 )(R 902 )(R 903 ),

[0640] -O-(R 904 ),

[0641] -S-(R 905 ),

[0642] -N(R 906 )(R 907 ),

[0643] a halogen atom, a cyano group, a nitro group,

[0644] a substituted or unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms, or

[0645] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-constituting atoms.

[0646] R 901 to R 907 are as defined in R 1 to R 8 .

[0647] Two or more adjacent ones among R 11B to R 18B do not bond to each other to form a ring.

[0648] R 1 to R 8 may all be deuterium atoms, or a part thereof (for example, one or more) may be deuterium atoms.

[0649] R 1 to R 8 that are not deuterium atoms are preferably hydrogen atoms (protium atoms).

[0650] In one embodiment, at least one of the hydrogen atoms possessed by one or more selected from L 1B and L 2B is a deuterium atom. Specifically, in one embodiment, one or more selected from L 1B and L 2B are an unsubstituted arylene group having 6 to 30 ring-constituting carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or a divalent heterocyclic group having 5 to 30 ring-constituting atoms in which at least one of the hydrogen atoms is a deuterium atom.

[0651] In one embodiment, L 1B and L 2B are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring-constituting carbon atoms. Preferably, at least one of L 1B and L 2B is a single bond.

[0652] In one embodiment, those among R 11B to R 18B that are not single bonds bonded to L 1B are hydrogen atoms.

[0653] In one embodiment, R 11B ~R 18B Among them, at least one that is not a single bond bonded to L 1B is a deuterium atom.

[0654] In one embodiment, at least one of the hydrogen atoms possessed by Ar 2B is a deuterium atom. Specifically, in one embodiment, Ar 2B is an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or a monovalent heterocyclic group having 5 to 50 ring-forming atoms in which at least one of the hydrogen atoms is a deuterium atom.

[0655] Ar 2B is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and more preferably selected from the groups represented by the following formulas (a1B) to (a4B).

[0656] [Chemical formula 22]

[0657]

[0658] In formulas (a1B) to (a4B), * is a single bond bonded to L 2B bond.

[0659] R 21B is:

[0660] a halogen atom, a cyano group, a nitro group,

[0661] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0662] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0663] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0664] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0665] -Si(R 901 )(R 902 )(R 903 ),

[0666] -O-(R 904 ),

[0667] -S-(R 905 ),

[0668] -N(R 906 )(R 907 ),

[0669] Aryl having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or

[0670] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[0671] R 901 ~R 907 as defined in the aforementioned formula (1).

[0672] m1B is an integer of 0 to 4.

[0673] m2B is an integer of 0 to 5.

[0674] m3B is an integer of 0 to 7.

[0675] When each of m1B to m3B is 2 or more, multiple Rs 21B may be the same or different from each other.

[0676] When each of m1B to m3B is 2 or more, adjacent multiple Rs 21B bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0677] L 1B and L 2B are each preferably independently a single bond, or a substituted or unsubstituted arylene having 6 to 14 ring-forming carbon atoms. Preferably, at least one of L 1B and L 2B is a single bond.

[0678] In one embodiment, the compound represented by formula (1B) is a compound represented by the following formula (1B-1).

[0679] [Chemical formula 23]

[0680]

[0681] In formula (1B-1), R 1 ~R 8 、Ar 2B 、L 1B and L 2B are as defined in the aforementioned formula (1B).

[0682] In one embodiment, the compound represented by formula (1B) is a compound represented by the following formula (1B-2).

[0683] [Chemical formula 24]

[0684]

[0685] In formula (1B-2), Ar 2 、L1B and L 2B As defined in the aforementioned formula (1B).

[0686] The compound represented by formula (1B) can be synthesized by using known alternative reactions and raw materials corresponding to the target through the synthesis methods described in the examples.

[0687] Specific examples of the compound represented by formula (1B) are shown below. In the following specific examples, D represents a deuterium atom.

[0688] [Chemical formula 25]

[0689]

[0690] [Chemical formula 26]

[0691]

[0692] [Chemical formula 27]

[0693]

[0694] [Chemical formula 28]

[0695]

[0696] [Chemical formula 29]

[0697]

[0698] [Chemical formula 30]

[0699]

[0700] [Chemical formula 31]

[0701]

[0702] [Chemical formula 32]

[0703]

[0704] [Chemical formula 33]

[0705]

[0706] [Chemical formula 34]

[0707]

[0708] [Chemical formula 35]

[0709]

[0710] [Chemical formula 36]

[0711]

[0712] [Chemical formula 37]

[0713]

[0714] [Chemical formula 38]

[0715]

[0716] [Chemical formula 39]

[0717]

[0718] [Chemical formula 40]

[0719]

[0720] [Chemical formula 41]

[0721]

[0722] [Chemical formula 42]

[0723]

[0724] [Chemical formula 43]

[0725]

[0726] [Chemical formula 44]

[0727]

[0728] [Chemical formula 45]

[0729]

[0730] [Chemical formula 46]

[0731]

[0732] The third form of the compound represented by the aforementioned formula (1) is the compound represented by the following formula (1C).

[0733] [Chemical formula 47]

[0734]

[0735] In formula (1C),

[0736] R 1 ~R 8 Each is independently:[

[0737] a hydrogen atom,[

[0738] An alkyl group having 1 to 50 carbon atoms, which may or may not be substituted,

[0739] An alkenyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[0740] An alkynyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[0741] A cycloalkyl group having 3 to 50 ring-constituting carbon atoms, which may or may not be substituted,

[0742] -Si(R 901 )(R 902 )(R 903 ),

[0743] -O-(R 904 ),

[0744] -S-(R 905 ),

[0745] -N(R 906 )(R 907 ),

[0746] A halogen atom, a cyano group, a nitro group,

[0747] An aryl group having 6 to 50 ring-constituting carbon atoms, which may or may not be substituted, or

[0748] A monovalent heterocyclic group having 5 to 50 ring-constituting atoms, which may or may not be substituted.

[0749] R 901 to R 907 are each independently:

[0750] A hydrogen atom,

[0751] An alkyl group having 1 to 50 carbon atoms, which may or may not be substituted,

[0752] A cycloalkyl group having 3 to 50 ring-constituting carbon atoms, which may or may not be substituted,

[0753] An aryl group having 6 to 50 ring-constituting carbon atoms, which may or may not be substituted, or

[0754] A monovalent heterocyclic group having 5 to 50 ring-constituting atoms, which may or may not be substituted.

[0755] R 901 to R 907 When there are two or more of them, two or more of R 901 to R 907 may be the same or different from each other.

[0756] At least one of R 1 to R 8 is a deuterium atom.

[0757] R 1 ~R 4 Two or more adjacent ones among and R 5 ~R 8 Two or more adjacent ones do not bond to each other to form a ring.

[0758] L 1C and L 2C Each independently is:

[0759] A single bond,

[0760] A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0761] A divalent heterocyclic group having 5 to 30 ring atoms which is substituted or unsubstituted.

[0762] Ar 2C Is:

[0763] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0764] A monovalent heterocyclic group having 5 to 50 ring atoms which is substituted or unsubstituted.

[0765] Ar 1C Is a monovalent group represented by the following formula (2C), (3C) or (4C).

[0766] [Chemical formula 48]

[0767]

[0768] In formulas (2C) to (4C),

[0769] R 15C ~R 20C One or more groups of two adjacent ones among bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0770] R 15C ~R 20C When one or more groups of two adjacent ones among do not bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, one of R 11C ~R 20C is a single bond bonded to L 1C bond.

[0771] R 15C ~R 20C When one or more groups of two adjacent ones among bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, R 15C ~R20C , and R 11C ~R 14C One of them is a single bond bonded to L 1C single bond.

[0772] Do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring and is not a single bond bonded to L 1C The R of the single bond 11C ~R 20C Are each independently:

[0773] A hydrogen atom,

[0774] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0775] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0776] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0777] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[0778] -Si(R 901 )(R 902 )(R 903 ),

[0779] -O-(R 904 ),

[0780] -S-(R 905 ),

[0781] -N(R 906 )(R 907 ),

[0782] A halogen atom, a cyano group, a nitro group,

[0783] A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[0784] A monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[0785] R 901 ~R 907 As defined in the aforementioned formula (1C).

[0786] R 1 ~R 8 May all be deuterium atoms, or a part thereof (for example, one or more) may be deuterium atoms.

[0787] R that is not a deuterium atom 1 ~R 8 Is preferably a hydrogen atom (protium atom).

[0788] In one embodiment, at least one of the hydrogen atoms possessed by one or more selected from L 1C and L 2C is a deuterium atom. Specifically, in one embodiment, one or more selected from L 1C and L 2C is an unsubstituted arylene group having 6 to 30 ring-constituting carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or a divalent heterocyclic group having 5 to 30 ring-constituting atoms in which at least one of the hydrogen atoms is a deuterium atom.

[0789] In one embodiment, L 1C and L 2C are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring-constituting carbon atoms. Preferably, at least one of L 1C and L 2C is a single bond.

[0790] In one embodiment, any one of R 11C to R 14C in formulas (2C) to (4C) is a single bond bonded to L 1C .

[0791] In one embodiment, in R 15C to R 20C in formulas (2C) to (4C), one or more groups of two adjacent ones do not bond to each other to form a substituted or unsubstituted saturated or unsaturated ring.

[0792] In one embodiment, in R 11C to R 20C in formulas (2C) to (4C), those that are not a single bond bonded to L 1C and do not contribute to ring formation are preferably hydrogen atoms.

[0793] In one embodiment, at least one of the hydrogen atoms possessed by Ar 11C to R 20C is a deuterium atom. Specifically, in one embodiment, Ar 1C is an unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or a monovalent heterocyclic group having 5 to 50 ring-constituting atoms in which at least one of the hydrogen atoms is a deuterium atom.

[0794] In one embodiment, at least one of the hydrogen atoms possessed by Ar 2C is a deuterium atom. Specifically, in one embodiment, Ar 2C is an unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms in which at least one of the hydrogen atoms is a deuterium atom, or a monovalent heterocyclic group having 5 to 50 ring-constituting atoms in which at least one of the hydrogen atoms is a deuterium atom.

[0795] Ar 2CPreferably, it is an optionally substituted aryl group having 6 to 50 ring carbon atoms, more preferably selected from the groups represented by the following formulas (a1C) to (a4C).

[0796] [Chemical formula 49]

[0797]

[0798] In formulas (a1C) to (a4C), * is a single bond bonded to L 2C bond.

[0799] R 21C is:

[0800] a halogen atom, a cyano group, a nitro group,

[0801] an optionally substituted alkyl group having 1 to 50 carbon atoms,

[0802] an optionally substituted alkenyl group having 2 to 50 carbon atoms,

[0803] an optionally substituted alkynyl group having 2 to 50 carbon atoms,

[0804] an optionally substituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0805] -Si(R 901 )(R 902 )(R 903 ),

[0806] -O-(R 904 ),

[0807] -S-(R 905 ),

[0808] -N(R 906 )(R 907 ),

[0809] an optionally substituted aryl group having 6 to 50 ring carbon atoms, or

[0810] an optionally substituted monovalent heterocyclic group having 5 to 50 ring atoms.

[0811] R 901 to R 907 are defined as in the aforementioned formula (1C).

[0812] m1C is an integer from 0 to 4.

[0813] m2C is an integer from 0 to 5.

[0814] m3C is an integer from 0 to 7.

[0815] When m1C to m3C are each 2 or more, multiple Rs21C They may be the same as or different from each other.

[0816] When there are two or more of m1C to m3C, multiple adjacent Rs 21 bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0817] L 1C and L 2C are each preferably independently a single bond or a substituted or unsubstituted arylene having 6 to 14 ring-forming carbon atoms. Preferably, L 1C and L 2C at least one of them is a single bond.

[0818] In one embodiment, the compound represented by formula (1C) is a compound represented by any one of the following formulas (1C-1) to (1C-3).

[0819] [Chemical formula 50]

[0820]

[0821] In formulas (1C-1) to (1C-3), R 1 to R 8 , Ar 2C , L 1C and L 2C are as defined in the aforementioned formula (1C).

[0822] In one embodiment, the compound represented by formula (1C) is a compound represented by any one of the following formulas (1C-11) to (1C-13).

[0823] [Chemical formula 51]

[0824]

[0825] In formulas (1C-11) to (1C-13), Ar 2C , L 1C and L 2C are as defined in the aforementioned formula (1C).

[0826] The compound represented by formula (1C) can be synthesized by using known alternative reactions and raw materials corresponding to the target through the synthesis methods described in the examples.

[0827] Specific examples of the compound represented by formula (1C) are shown below. In the following specific examples, D represents a deuterium atom.

[0828] [Chemical formula 52]

[0829]

[0830] [Chemical Formula 53]

[0831]

[0832] [Chemical Formula 54]

[0833]

[0834] [Chemical Formula 55]

[0835]

[0836] [Chemical Formula 56]

[0837]

[0838] [Chemical Formula 57]

[0839]

[0840] [Chemical Formula 58]

[0841]

[0842] [Chemical Formula 59]

[0843]

[0844] [Chemical Formula 60]

[0845]

[0846] [Chemical Formula 61]

[0847]

[0848] [Chemical Formula 62]

[0849]

[0850] [Chemical Formula 63]

[0851]

[0852] [Chemical Formula 64]

[0853]

[0854] [Chemical Formula 65]

[0855]

[0856] [Chemical Formula 66]

[0857]

[0858] [Chemical Formula 67]

[0859]

[0860] [Chemical Formula 68]

[0861]

[0862] [Chemical Formula 69]

[0863]

[0864] [Chemical Formula 70]

[0865]

[0866] [Chemical Formula 71]

[0867]

[0868] [Chemical Formula 72]

[0869]

[0870] [Chemical Formula 73]

[0871]

[0872] [Chemical Formula 74]

[0873]

[0874] [Chemical Formula 75]

[0875]

[0876] [Chemical Formula 76]

[0877]

[0878] [Chemical Formula 77]

[0879]

[0880] [Chemical Formula 78]

[0881]

[0882] [Chemical Formula 79]

[0883]

[0884] [Chemical Formula 80]

[0885]

[0886] [Chemical Formula 81]

[0887]

[0888] [Chemical Formula 82]

[0889]

[0890] [Chemical Formula 83]

[0891]

[0892] [Chemical Formula 84]

[0893]

[0894] [Chemical Formula 85]

[0895]

[0896] [Chemical Formula 86]

[0897]

[0898] [Chemical Formula 87]

[0899]

[0900] [Chemical Formula 88]

[0901]

[0902] [Chemical Formula 89]

[0903]

[0904] [Chemical Formula 90]

[0905]

[0906] [Chemical Formula 91]

[0907]

[0908] [Chemical Formula 92]

[0909]

[0910] [Chemical Formula 93]

[0911]

[0912] [Chemical Formula 94]

[0913]

[0914] [Chemical Formula 95]

[0915]

[0916] [Chemical Formula 96]

[0917]

[0918] [Chemical Formula 97]

[0919]

[0920] [Chemical Formula 98]

[0921]

[0922] [Chemical Formula 99]

[0923]

[0924] [Chemical Formula 100]

[0925]

[0926] The dopant material is not particularly limited. As described above, it preferably does not contain a phosphorescent dopant material.

[0927] Examples of the dopant material include compounds represented by the following formulas (11), (21), (31), (41), (51), (61), (71), (81), and (91). A compound represented by the following formula (11) is preferred.

[0928] (Compound represented by formula (11))

[0929] The compound represented by formula (11) will be described.

[0930] [Chemical Formula 101]

[0931]

[0932] In formula (11),

[0933] R 101 ~R 110 Two or more adjacent ones in a group of one or more bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0934] R 101 ~R 110 At least one of them is a monovalent group represented by the following formula (12).

[0935] R 101 ~R 110Each independently is:

[0936] a hydrogen atom,

[0937] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[0939] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0940] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0941] -Si(R 901 )(R 902 )(R 903 ),

[0942] -O-(R 904 ),

[0943] -S-(R 905 ),

[0944] -N(R 906 )(R 907 ),

[0945] a halogen atom, a cyano group, a nitro group,

[0946] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0947] a monovalent heterocyclic group having 5 to 50 ring atoms which may be substituted or unsubstituted.

[0948] R 901 to R 907 are as defined in the aforementioned formula (1).

[0949] [Chemical formula 102]

[0950]

[0951] In formula (12), Ar 101 and Ar 102 each independently is:

[0952] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0953] a monovalent heterocyclic group having 5 to 50 ring atoms which may be substituted or unsubstituted.

[0954] L 101 to L 103 each independently is:

[0955] a single bond,

[0956] Arylene having 6 to 30 ring-forming carbon atoms, which may be substituted or unsubstituted, or

[0957] a divalent heterocyclic group having 5 to 30 ring-forming atoms, which may be substituted or unsubstituted.

[0958] In formula (11), preferably, two of R 101 ~R 110 are groups represented by formula (12).

[0959] In one embodiment, the compound represented by formula (11) is represented by the following formula (13).

[0960] [Chemical formula 103]

[0961]

[0962] In formula (13), R 111 ~R 118 are the same as R 101 ~R 110 in the aforementioned formula (11) which are monovalent groups not represented by formula (12). Ar 101 、Ar 102 、L 101 、L 102 and L 103 are as defined in the aforementioned formula (12).

[0963] In formula (11), L 101 is preferably a single bond, and L 102 and L 103 are preferably single bonds.

[0964] In one embodiment, the compound represented by formula (11) is represented by the following formula (14) or (15).

[0965] [Chemical formula 104]

[0966]

[0967] In formula (14), R 111 ~R 118 are as defined in the aforementioned formula (13). Ar 101 、Ar 102 、L 102 and L 103 are as defined in the aforementioned formula (12).

[0968] [Chemical formula 105]

[0969]

[0970] In formula (15), R 111 ~R 118As defined in the aforementioned formula (13). Ar 101 and Ar 102 As defined in the aforementioned formula (12).

[0971] In formula (12) of formula (11), preferably Ar 101 and Ar 102 At least one of them is a group represented by the following formula (16).

[0972] [Chemical 106]

[0973]

[0974] In formula (16),

[0975] X 101 Represents an oxygen atom or a sulfur atom.

[0976] R 121 ~R 127 Among them, two or more adjacent ones bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[0977] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 121 ~R 127 Each independently is:[[]]

[0978] A hydrogen atom,[[]]

[0979] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,[[]]

[0980] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,[[]]

[0981] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,[[]]

[0982] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,[[]]

[0983] -Si(R 901 )(R 902 )(R 903 ),[[]]

[0984] -O-(R 904 ),[[]]

[0985] -S-(R 905 ),[[]]

[0986] -N(R 906 )(R 907 ),[[]]

[0987] A halogen atom, a cyano group, a nitro group,[[]]

[0988] An aryl group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, or

[0989] a monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted.

[0990] R 901 ~R 907 is as defined in the aforementioned formula (1).

[0991] X 101 is preferably an oxygen atom.

[0992] R 121 ~R 127 At least one of them is preferably:

[0993] an alkyl group having 1 to 50 carbon atoms, which may or may not be substituted,

[0994] an alkenyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[0995] an alkynyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[0996] a cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may or may not be substituted,

[0997] an aryl group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, or

[0998] a monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted.

[0999] In formula (11) (formula (12)), preferably Ar 101 is a group represented by formula (16), and Ar 102 is an aryl group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted.

[1000] In one embodiment, the compound represented by formula (11) is represented by the following formula (17).

[1001] [Chemical 107]

[1002]

[1003] In formula (17), R 111 ~R 118 is as defined in the aforementioned formula (13). R 121 ~R 127 is as defined in the aforementioned formula (16).

[1004] R 131 ~R 135 Each independently is:

[1005] a hydrogen atom,

[1006] An alkyl group having 1 to 50 carbon atoms, which may or may not be substituted,

[1007] An alkenyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[1008] An alkynyl group having 2 to 50 carbon atoms, which may or may not be substituted,

[1009] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may or may not be substituted,

[1010] -Si(R 901 )(R 902 )(R 903 ),

[1011] -O-(R 904 ),

[1012] -S-(R 905 ),

[1013] -N(R 906 )(R 907 ),

[1014] A halogen atom, a cyano group, a nitro group,

[1015] An aryl group having 6 to 50 ring-forming carbon atoms, which may or may not be substituted, or

[1016] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may or may not be substituted.

[1017] R 901 to R 907 are as defined in the aforementioned formula (1).

[1018] As the compound represented by the formula (11), specific examples thereof include the compounds shown below. In the following specific examples, Me represents a methyl group.

[1019] [Chemical formula 108]

[1020]

[1021] [Chemical formula 109]

[1022]

[1023] [Chemical formula 110]

[1024]

[1025] [Chemical formula 111]

[1026]

[1027] [Chemical formula 112]

[1028]

[1029] [Chemical formula 113]

[1030]

[1031] [Chemical formula 114]

[1032]

[1033] (Compound represented by formula (21))

[1034] The compound represented by formula (21) will be described.

[1035] [Chemical formula 115]

[1036]

[1037] In formula (21),

[1038] Z is each independently CR a or N.

[1039] The A1 ring and the A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-constituting carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring-constituting atoms.

[1040] R a When there are a plurality of R's, a two or more adjacent ones of the plurality of R's 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.

[1041] R b When there are a plurality of R's, b two or more adjacent ones of the plurality of R's 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.

[1042] R c When there are a plurality of R's, c two or more adjacent ones of the plurality of R's 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.

[1043] n21 and n22 are each independently an integer of 0 to 4.

[1044] R's that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring a to R c are each independently:

[1045] A hydrogen atom,

[1046] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1047] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1048] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1049] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1050] -Si(R 901 )(R 902 )(R 903 ),

[1051] -O-(R 904 ),

[1052] -S-(R 905 ),

[1053] -N(R 906 )(R 907 ),

[1054] a halogen atom, a cyano group, a nitro group,

[1055] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1056] a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted or unsubstituted.

[1057] R 901 to R 907 are as defined in the aforementioned formula (1).

[1058] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound formed by introducing a hydrogen atom into the above-mentioned "aryl group". The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring includes 2 carbon atoms on the fused bicyclic structure in the center of formula (21) as ring-forming atoms. As a specific example of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms", mention may be made of the compound formed by introducing a hydrogen atom into the "aryl group" described in specific example group G1, etc.

[1059] The "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound formed by introducing a hydrogen atom into the above-mentioned "heterocyclic group". The "heterocycle" of the A1 ring and the A2 ring includes 2 carbon atoms on the fused bicyclic structure in the center of formula (21) as ring-forming atoms. As a specific example of the "substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms", mention may be made of the compound formed by introducing a hydrogen atom into the "heterocyclic group" described in specific example group G2, etc.

[1060] R bBonded to any one of the carbon atoms of the aromatic hydrocarbon ring forming the A1 ring, or bonded to any one of the atoms of the heterocyclic ring forming the A1 ring.

[1061] R c Bonded to any one of the carbon atoms of the aromatic hydrocarbon ring forming the A2 ring, or bonded to any one of the atoms of the heterocyclic ring forming the A2 ring.

[1062] Preferably R a ~R c At least one (preferably two) of them is a group represented by the following formula (21a).

[1063] -L 201 -Ar 201 (21a)

[1064] In formula (21a),

[1065] L 201 is:

[1066] A single bond,

[1067] A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1068] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1069] Ar 201 is:

[1070] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1071] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[1072] A group represented by the following formula (21b).

[1073] [Chemical formula 116]

[1074]

[1075] In formula (21b),

[1076] L 211 and L 212 each independently is:

[1077] A single bond,

[1078] A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1079] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1080] Ar 211and Ar 212 bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1081] Ar that does not form a substituted or unsubstituted saturated or unsaturated ring 211 and Ar 212 are each independently:

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

[1083] a monovalent heterocyclic group having 5 to 50 ring atoms, which may be substituted or unsubstituted.

[1084] In one embodiment, the compound represented by formula (21) is represented by the following formula (22).

[1085] [Chemical 117]

[1086]

[1087] In formula (22),

[1088] R 201 ~R 211 Two or more adjacent groups among them bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1089] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 201 ~R 211 are each independently:

[1090] a hydrogen atom,

[1091] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1092] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1093] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1094] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1095] -Si(R 901 )(R 902 )(R 903 ),

[1096] -O-(R 904 ),

[1097] -S-(R 905 ),

[1098] -N(R 906 )(R 907 ),

[1099] a halogen atom, a cyano group, a nitro group,

[1100] an aryl group having 6 to 50 ring-constituting carbon atoms which is substituted or unsubstituted, or

[1101] a monovalent heterocyclic group having 5 to 50 ring-constituting atoms which is substituted or unsubstituted.

[1102] R 901 to R 907 are as defined in the aforementioned formula (1).

[1103] Preferably, at least one (preferably two) of R 201 to R 211 is the group represented by the above formula (21a). Preferably, R 204 and R 211 are the groups represented by the above formula (21a).

[1104] In one embodiment, the compound represented by formula (21) is a compound in which a structure represented by the following formula (21-1) or (21-2) is bonded to the A1 ring. Further, in one embodiment, the compound represented by formula (22) is a compound in which a structure represented by the following formula (21-1) or (21-2) is bonded to the ring to which R 204 to R 207 is bonded.

[1105] [Chemical 118]

[1106]

[1107] In formula (21-1), the two bonding bonds * are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring of the A1 ring of formula (21) or a ring-constituting atom of the heterocycle, or to any one of R 204 to R 207 of formula (22).

[1108] In formula (21-2), the three bonding bonds * are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring of the A1 ring of formula (22) or a ring-constituting atom of the heterocycle, or to any one of R 204 to R 207 of formula (22).

[1109] Two or more adjacent ones of R 221 to R 227 and R 231 to R 239 bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1110] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 221 ~R 227 and R 231 ~R 239 are each independently:

[1111] a hydrogen atom,

[1112] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1113] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1114] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1115] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1116] -Si(R 901 )(R 902 )(R 903 ),

[1117] -O-(R 904 ),

[1118] -S-(R 905 ),

[1119] -N(R 906 )(R 907 ),

[1120] a halogen atom, a cyano group, a nitro group,

[1121] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1122] a monovalent heterocyclic group having 5 to 50 ring-forming atoms that is substituted or unsubstituted.

[1123] R 901 ~R 907 is as defined in the aforementioned formula (1).

[1124] 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).

[1125] [Chemical 119]

[1126]

[1127] In formula (21-3), formula (21-4), and formula (21-5),

[1128] the A1 ring is as defined in formula (21).

[1129] R 2401 ~R 2407 is the same as R in Formulas (21-1) and (21-2). 221 ~R 227 is the same as R. R 2410 ~R 2417 is the same as R in Formula (22). 201 ~R 211 is the same.

[1130] In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms in the A1 ring of Formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted fluorene ring.

[1131] In one embodiment, the heterocyclic ring having 5 to 50 ring-forming 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.

[1132] 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).

[1133] [Chemical 120]

[1134]

[1135] In Formulas (21-6-1) to (21-6-7),

[1136] R 2421 ~R 2427 is the same as R in Formulas (21-1) and (21-2). 221 ~R 227 is the same as R. R 2430 ~R 2437 and R 2441 ~R 2444 is the same as R in Formula (22). 201 ~R 211 is the same.

[1137] X is O, NR 901 , or C(R 902 )(R 903 ).

[1138] R 901 ~R 903 is defined as in the aforementioned Formula (1).

[1139] In one embodiment, in the compound represented by Formula (22), R 201 ~R 211Two or more adjacent groups of two or more are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. This embodiment will be described in detail in the following formula (25).

[1140] (Compound represented by formula (25))

[1141] The compound represented by formula (25) will be described.

[1142] [Chemical formula 121]

[1143]

[1144] In formula (25),

[1145] Selected from R 251 And R 252 , R 252 And R 253 , R 254 And R 255 , R 255 And R 256 , R 256 And R 257 , R 258 And R 259 , R 259 And R 260 , and R 260 And R 261 Two or more pairs of the pairs among them are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring.

[1146] Among them, the pair composed of R 251 And R 252 And the pair composed of R 252 And R 253 ; The pair composed of R 254 And R 255 And the pair composed of R 255 And R 256 ; The pair composed of R 255 And R 256 And the pair composed of R 256 And R 257 ; The pair composed of R 258 And R 259 And the pair composed of R 259 And R 260 ; And the pair composed of R 259 And R 260 And the pair composed of R 260 And R 261 Do not form a ring at the same time.

[1147] R 251 ~R 261Two or more formed rings may be the same or different.

[1148] R that does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 251 ~R 261 Each independently is:

[1149] A hydrogen atom,

[1150] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1151] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1152] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1153] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1154] -Si(R 901 )(R 902 )(R 903 ),

[1155] -O-(R 904 ),

[1156] -S-(R 905 ),

[1157] -N(R 906 )(R 907 ),

[1158] A halogen atom, a cyano group, a nitro group,

[1159] A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1160] A monovalent heterocyclic group having 5 to 50 ring-forming atoms that is substituted or unsubstituted.

[1161] R 901 ~R 907 Is as defined in the aforementioned formula (1).

[1162] In formula (25), R n and R n＋1 (n represents an integer selected from 251, 252, 254 to 256, and 258 to 260) are bonded to each other and together with the two ring-forming carbon atoms to which R n and R n＋1 are bonded form a substituted or unsubstituted saturated or unsaturated ring. This 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.

[1163] The number of the above-mentioned ring structures in the compound represented by the formula (25) is, for example, 2, 3, or 4. Two or more ring structures may each be present on the same benzene ring of the parent skeleton of the formula (25) or on different benzene rings. For example, when there are 3 ring structures, each of the 3 benzene rings of the formula (25) may have 1 ring structure.

[1164] Examples of the above-mentioned ring structure in the compound represented by the formula (25) include structures represented by the following formulas (251) to (260) and the like.

[1165] [Chemical Formula 122]

[1166]

[1167] In the 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 each represent R n and R n＋1 the two ring-forming carbon atoms to which they are bonded, and the ring-forming carbon atom to which R n is bonded may be any one of the 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.

[1168] X 2501 is C(R 2512 )(R 2513 ), NR 2514 ), O, or S.

[1169] R 2501 to R 2506 and R 2512 to R 2513 Two or more adjacent groups of two or more bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1170] R 2501 to R 2514 that do not form a substituted or unsubstituted saturated or unsaturated ring are the same as the aforementioned R 251 to R 261 .

[1171] [Chemical Formula 123]

[1172]

[1173] In the formulas (258) to (260), *1 and *2, and *3 and *4 each represent R n and R n＋1 the two ring-forming carbon atoms to which they are bonded, Rn The ring-forming carbon atoms to be bonded can be any one of the two ring-forming carbon atoms represented by *1 and *2, or *3 and *4.

[1174] X 2501 is C(R 2512 )(R 2513 ), NR 2514 , O or S.

[1175] R 2515 ~~R 2525 Two or more adjacent ones among R

[1176] bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. 2515 ~R 2521 and R 2522 ~R 2525 are the same as the aforementioned R 251 ~R 261 .

[1177] In formula (25), preferably at least one of R 252 , R 254 , R 255 , R 260 and R 261 (preferably at least one of R 252 , R 255 and R 260 ; more preferably R 252 ) is a group that does not form a ring structure.

[1178] (i) In formula (25), when the ring structure formed by R n and R n＋1 has a substituent, the substituent,

[1179] (ii) In formula (25), R 251 ~R 261 that do not form a ring structure, and

[1180] (iii) R 2501 ~R 2514 , R 2515 ~~R 2525 in formulas (251) to (260) are preferably each independently:

[1181] a hydrogen atom,

[1182] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1183] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1184] An alkynyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1185] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted,

[1186] -N(R 906 )(R 907 ),

[1187] An aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted,

[1188] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted, or

[1189] Any one of the groups selected from the following groups.

[1190] [Chemical formula 124]

[1191]

[1192] In formulas (261) to (264), R d are each independently:

[1193] A hydrogen atom,

[1194] An alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[1195] An alkenyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1196] An alkynyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1197] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted,

[1198] -Si(R 901 )(R 902 )(R 903 ),

[1199] -O-(R 904 ),

[1200] -S-(R 905 ),

[1201] -N(R 906 )(R 907 ),

[1202] A halogen atom, a cyano group, a nitro group,

[1203] An aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or

[1204] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[1205] X is C(R 901 )(R 902 ), NR 903 , O or S.

[1206] R 901 ~R 907 is defined as in the aforementioned formula (1).

[1207] p1 is independently an integer from 0 to 5, p2 is independently an integer from 0 to 4, p3 is an integer from 0 to 3, and p4 is an integer from 0 to 7.

[1208] In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-1) to (25-6).

[1209] [Chemical Formula 125]

[1210]

[1211] 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 is the same as in the aforementioned formula (25).

[1212] In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-7) to (25-12).

[1213] [Chemical Formula 126]

[1214]

[1215] In formulas (25-7) to (25-12), rings d to f, k, j are each independently a substituted or unsubstituted saturated or unsaturated ring. R 251 ~R 261 is the same as in the aforementioned formula (25).

[1216] In one embodiment, the compound represented by formula (25) is represented by any one of the following formulas (25-13) to (25-21).

[1217] [Chemical Formula 127]

[1218]

[1219] 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 is the same as in the aforementioned formula (25).

[1220] Examples of the substituent when the aforementioned ring g or h further has a substituent include:

[1221] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1222] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1223] a group represented by the aforementioned formula (261), (263), or (264).

[1224] In one embodiment, the compound represented by the formula (25) is represented by any one of the following formulas (25-22) to (25-25).

[1225] [Chemical Formula 128]

[1226]

[1227] In formulas (25-22) to (25-25), X 250 is independently C(R 901 )(R 902 ), NR 903 , O, or S. R 251 to R 261 , R 271 to R 278 are the same as R 251 to R 261 in the aforementioned formula (25). R 901 to R 903 are as defined in the aforementioned formula (1).

[1228] In one embodiment, the compound represented by the formula (25) is represented by the following formula (25-26).

[1229] [Chemical Formula 129]

[1230]

[1231] In formula (25-26), X 250 is C(R 901 )(R 902 ), NR 903 , O, or S. R 253 , R 254 , R 257 , R 258 , R 261 , and R 271 to R 282 are the same as R 251 to R 261 in the aforementioned formula (25). R 901 to R 903 are as defined in the aforementioned formula (1).

[1232] As the compound represented by formula (21), specific examples include the compounds shown below. In the following specific examples, Me represents a methyl group.

[1233] In these specific examples, there is no Ph and D.

[1234] [Chemical formula 130]

[1235]

[1236] [Chemical formula 131]

[1237]

[1238] [Chemical formula 132]

[1239]

[1240] [Chemical formula 133]

[1241]

[1242] [Chemical formula 134]

[1243]

[1244] [Chemical formula 135]

[1245]

[1246] [Chemical formula 136]

[1247]

[1248] [Chemical formula 137]

[1249]

[1250] [Chemical formula 138]

[1251]

[1252] [Chemical formula 139]

[1253]

[1254] (Compound represented by formula (31))

[1255] The compound represented by formula (31) will be described. The compound represented by formula (31) is the compound corresponding to the compound represented by the above formula (21-3).

[1256] [Chemical formula 140]

[1257]

[1258] In formula (31),

[1259] R 301 ~R 307 and R 311 ~R 317 form one or more groups of two or more adjacent ones to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1260] R 301 ~R 307 and R 311 ~R 317 are each independently:

[1261] a hydrogen atom,

[1262] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1263] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1264] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1265] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1266] -Si(R 901 )(R 902 )(R 903 ),

[1267] -O-(R 904 ),

[1268] -S-(R 905 ),

[1269] -N(R 906 )(R 907 ),

[1270] a halogen atom, a cyano group, a nitro group,

[1271] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1272] a monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1273] R 321 and R 322 are each independently:

[1274] a hydrogen atom,

[1275] An alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[1276] An alkenyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1277] An alkynyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1278] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted,

[1279] -Si(R 901 )(R 902 )(R 903 ),

[1280] -O-(R 904 ),

[1281] -S-(R 905 ),

[1282] -N(R 906 )(R 907 ),

[1283] A halogen atom, a cyano group, a nitro group,

[1284] An aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or

[1285] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[1286] R 901 ~R 907 Is defined as in the aforementioned formula (1).

[1287] "Two or more adjacent ones in "R 301 ~R 307 and R 311 ~R 317 " For example, it is a combination of R 301 and R 302 , R 302 and R 303 , R 303 and R 304 , R 305 and R 306 , R 306 and R 307 , R 301 and R 302 and R 303 and so on.

[1288] In one embodiment, at least one, preferably two, of R 301 ~R 307 and R 311 ~R 317 are -N(R906 )(R 907 ) the group shown.

[1289] In one embodiment, R 301 ~R 307 and R 311 ~R 317 are each 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.

[1290] In one embodiment, the compound represented by formula (31) is the compound represented by the following formula (32).

[1291] [Chemical 141]

[1292]

[1293] In formula (32),

[1294] R 331 ~R 334 and R 341 ~R 344 Two or more adjacent groups among them form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1295] R 331 ~R 334 , R 341 ~R 344 , and R 351 and R 352 are each independently:

[1296] a hydrogen atom,

[1297] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1298] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1299] R 361 ~R 364 are each independently:

[1300] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1301] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1302] In one embodiment, the compound represented by formula (31) is the compound represented by the following formula (33).

[1303] [Chemical 142]

[1304]

[1305] In formula (33), R 351 , R 352 and R 361 ~R 364 are defined as in the aforementioned formula (32).

[1306] In one embodiment, R 361 ~R 364 in formulas (32) and (33) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

[1307] In one embodiment, R 321 and R 322 in formula (31), R 351 and R 352 in formulas (32) and (33) are hydrogen atoms.

[1308] In one embodiment, the substituents in the case of "substituted or unsubstituted" in formulas (31) to (33) are:

[1309] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1310] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1311] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1312] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1313] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1314] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1315] As the compound represented by formula (31), specific examples include the compounds shown below.

[1316] [Chemical 143]

[1317]

[1318] [Chemical 144]

[1319]

[1320] [Chemical 145]

[1321]

[1322] [Chemical Formula 146]

[1323]

[1324] [Chemical Formula 147]

[1325]

[1326] [Chemical Formula 148]

[1327]

[1328] (Compound represented by formula (41))

[1329] The compound represented by formula (41) will be described.

[1330] [Chemical Formula 149]

[1331]

[1332] In formula (41),

[1333] Ring a, ring b, and ring c are each independently:[[]]

[1334] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or

[1335] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.

[1336] R 401 and R 402 Each independently bond to the aforementioned ring a, the aforementioned ring b, or the aforementioned ring c to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring.

[1337] R 401 and R 402 which do not form the aforementioned substituted or unsubstituted heterocyclic ring are each independently:[[]]

[1338] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1339] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1340] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1341] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1342] A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1343] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1344] Ring a, ring b, and ring c are rings (an aromatic hydrocarbon ring having 6 to 50 ring-constituting carbon atoms, which may be substituted or unsubstituted, or a heterocyclic ring having 5 to 50 ring-constituting atoms, which may be substituted or unsubstituted) fused to the central fused bicyclic structure of formula (41) composed of a B atom and two N atoms.

[1345] The "aromatic hydrocarbon ring" of ring a, ring b, and ring c has the same structure as the compound formed by introducing a hydrogen atom into the above-mentioned "aryl group". The "aromatic hydrocarbon ring" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (41) as ring-constituting atoms. The "aromatic hydrocarbon ring" of ring b and ring c contains two carbon atoms on the central fused bicyclic structure of formula (41) as ring-constituting atoms. As a specific example of the "aromatic hydrocarbon ring having 6 to 50 ring-constituting carbon atoms, which may be substituted or unsubstituted", compounds formed by introducing a hydrogen atom into the "aryl group" described in specific example group G1 can be cited, etc.

[1346] The "heterocyclic ring" of ring a, ring b, and ring c has the same structure as the compound formed by introducing a hydrogen atom into the above-mentioned "heterocyclic group". The "heterocyclic ring" of ring a contains three carbon atoms on the central fused bicyclic structure of formula (41) as ring-constituting atoms. The "heterocyclic ring" of ring b and ring c contains two carbon atoms on the central fused bicyclic structure of formula (41) as ring-constituting atoms. As a specific example of the "heterocyclic ring having 5 to 50 ring-constituting atoms, which may be substituted or unsubstituted", compounds formed by introducing a hydrogen atom into the "heterocyclic group" described in specific example group G2 can be cited, etc.

[1347] R 401 and R 402 may each independently bond to ring a, ring b, or ring c to form a substituted or unsubstituted heterocyclic ring. The heterocyclic ring in this case contains a nitrogen atom on the central fused bicyclic structure of formula (41). The heterocyclic ring in this case may further contain heteroatoms other than nitrogen atoms. R 401 and R 402 bonding to ring a, ring b, or ring c specifically means that the atoms constituting ring a, ring b, or ring c bond to the atoms constituting R 401 and R 402 For example, R 401 may bond to ring a to form a nitrogen-containing heterocyclic ring in which a ring containing R 401 is fused to ring a (or a fused ring of three or more rings). As a specific example of this nitrogen-containing heterocyclic ring, compounds corresponding to the heterocyclic groups containing nitrogen and having a fused ring of two or more rings in specific example group G2 can be cited, etc.

[1348] R 401 The case where it bonds to ring b, the case where R 402 bonds to ring a, and the case where R 402 bonds to ring c are the same as above.

[1349] In one embodiment, each of the a-ring, b-ring, and c-ring in formula (41) is independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms.

[1350] In one embodiment, each of the a-ring, b-ring, and c-ring in formula (41) is independently a substituted or unsubstituted benzene ring or naphthalene ring.

[1351] In one embodiment, R in formula (41) 401 and R 402 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[1352] In one embodiment, the compound represented by formula (41) is the compound represented by the following formula (42).

[1353] [Chemical Formula 150]

[1354]

[1355] In formula (42),

[1356] R 401A bonds to one or more selected from R 411 and R 421 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 402A bonds to one or more selected from R 413 and R 414 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.

[1357] R 401A and R 402A that do not form the aforementioned substituted or unsubstituted heterocycle are each independently:

[1358] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1359] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1360] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1361] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1362] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1363] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1364] R 411 ~R 421 Two or more adjacent groups among them 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.

[1365] 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 is:

[1366] A hydrogen atom,

[1367] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1368] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1369] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1370] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1371] -Si(R 901 )(R 902 )(R 903 ),

[1372] -O-(R 904 ),

[1373] -S-(R 905 ),

[1374] -N(R 906 )(R 907 ),

[1375] A halogen atom, a cyano group, a nitro group,

[1376] A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1377] A monovalent heterocyclic group having 5 to 50 ring-forming atoms that is substituted or unsubstituted.

[1378] R 901 ~R 907 Is as defined in the aforementioned formula (1).

[1379] R of formula (42) 401A and R 402A are groups corresponding to R 401 and R 402 of formula (41).

[1380] For example, R 401A and R 411They can be bonded to form a nitrogen-containing heterocycle having a 2-ring fusion (or a 3-ring fusion or more) in which the ring containing them is fused with a benzene ring corresponding to the a-ring. As a specific example of the nitrogen-containing heterocycle, compounds corresponding to the heterocyclic groups having a 2-ring fusion or more containing nitrogen in the specific example group G2 can be cited. R 401A The case of bonding with R 412 The case of bonding with R 402A The case of bonding with R 413 The case of bonding with R 402A The case of bonding with R 414 The case of bonding with R

[1381] R 411 ~R 421 Two or more of one or more adjacent ones among them can be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. For example, R 411 and R 412 can be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring is fused to the 6-membered ring to which they are bonded, and the formed fused ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[1382] In one embodiment, R 411 ~R 421 which do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1383] In one embodiment, R 411 ~R 421 which do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1384] In one embodiment, R 411 ~R 421 which do not contribute to ring formation are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1385] In one embodiment, R 411 ~R 421 which do not contribute to ring formation are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R 411 ~R 421 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1386] In one embodiment, the compound represented by the aforementioned formula (42) is the compound represented by the following formula (43).

[1387] [Chemical Formula 151]

[1388]

[1389] In formula (43),

[1390] R 431 bonds with R 446 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 433 bonds with R 447 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 434 bonds with R 451 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle. R 441 bonds with R 442 to form a substituted or unsubstituted heterocycle, or does not form a substituted or unsubstituted heterocycle.

[1391] R 431 ~R 451 bond with each other in groups of two or more adjacent ones to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1392] R 431 ~R 451 each independently is:

[1393] a hydrogen atom,

[1394] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1395] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1396] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1397] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1398] -Si(R 901 )(R 902 )(R 903 ),

[1399] -O-(R 904 ),

[1400] -S-(R 905 ),

[1401] -N(R 906 )(R907 ),

[1402] a halogen atom, a cyano group, a nitro group,

[1403] an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted, or

[1404] a monovalent heterocyclic group having 5 to 50 ring-constituting atoms which may be substituted or unsubstituted.

[1405] R 901 ~R 907 is as defined in the aforementioned formula (1).

[1406] R 431 may bond with R 446 to form a substituted or unsubstituted heterocycle. For example, R 431 and R 446 may bond to form a benzene ring to which R 46 is bonded, a ring containing N, and a nitrogen-containing heterocycle having 3 or more benzene ring fusions corresponding to the a ring. As a specific example of the nitrogen-containing heterocycle, a compound corresponding to a heterocyclic group having 3 or more benzene ring fusions containing nitrogen in the specific example group G2 etc. may be mentioned. The case where R 433 bonds with R 447 , the case where R 434 bonds with R 451 , and the case where R 441 bonds with R 442 are also the same as above.

[1407] In one embodiment, R 431 ~R 451 which do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-constituting atoms.

[1408] In one embodiment, R 431 ~R 451 which do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-constituting atoms.

[1409] In one embodiment, R 431 ~R 451 which do not contribute to ring formation are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1410] In one embodiment, R 431 ~R 451Each independently is 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.

[1411] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43A).

[1412] [Chemical formula 152]

[1413]

[1414] In formula (43A),

[1415] R 461 is:

[1416] a hydrogen atom,

[1417] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1418] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1419] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1420] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1421] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1422] R 462 ~R 465 Each independently is:

[1423] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

[1425] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1426] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1427] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1428] In one embodiment, R 461 ~R 465 Each independently is 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.

[1429] In one embodiment, R461 ~R 465 Each independently is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1430] In one embodiment, the compound represented by the aforementioned formula (43) is the compound represented by the following formula (43B).

[1431] [Chemical Formula 153]

[1432]

[1433] In formula (43B),

[1434] R 471 and R 472 Each independently is:

[1435] a hydrogen atom,

[1436] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1437] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1438] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1439] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1440] -N(R 906 )(R 907 ), or

[1441] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1442] R 473 ~R 475 Each independently is:

[1443] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1444] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1445] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1446] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1447] -N(R 906 )(R 907 ), or

[1448] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1449] R 906 and R907 As defined in the foregoing formula (1).

[1450] In one embodiment, the compound represented by the foregoing formula (43) is the compound represented by the following formula (43B').

[1451] [Chemical Formula 154]

[1452]

[1453] In formula (43B'), R 472 ~R 475 As defined in the foregoing formula (43B).

[1454] In one embodiment, at least one of R 471 ~R 475 is:

[1455] an alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[1456] an alkenyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1457] an alkynyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1458] a cycloalkyl group having 3 to 50 ring carbon atoms, which may be substituted or unsubstituted,

[1459] -N(R 906 )(R 907 ), or

[1460] an aryl group having 6 to 50 ring carbon atoms, which may be substituted or unsubstituted.

[1461] In one embodiment,

[1462] R 472 is:

[1463] a hydrogen atom,

[1464] an alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[1465] -N(R 906 )(R 907 ), or

[1466] an aryl group having 6 to 50 ring carbon atoms, which may be substituted or unsubstituted,

[1467] R 471 and R 473 ~R 475 are each independently:

[1468] an alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[1469] -N(R 906 )(R 907 ), or

[1470] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1471] In one embodiment, the compound represented by the foregoing formula (43) is a compound represented by the following formula (43C).

[1472] [Chemical formula 155]

[1473]

[1474] In formula (43C),

[1475] R 481 and R 482 are each independently:

[1476] a hydrogen atom,

[1477] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1478] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1479] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1480] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1481] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1482] R 483 to R 486 are each independently:

[1483] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1484] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1485] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1486] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1487] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1488] In one embodiment, the compound represented by the foregoing formula (43) is a compound represented by the following formula (43C').

[1489] [Chemical formula 156]

[1490]

[1491] In formula (43C'), R 483 ~R 486 is as defined in the aforementioned formula (43C).

[1492] In one embodiment, R 481 ~R 486 are each 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-forming carbon atoms.

[1493] In one embodiment, R 481 ~R 486 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

[1494] The compound represented by formula (41) can be prepared by first bonding the a-ring, b-ring, and c-ring with a linking group (a group containing N-R 1 and a group containing N-R 2 ) to produce an intermediate (the first reaction), and then bonding the a-ring, b-ring, and c-ring with a linking group (a group containing B) to produce the final product (the second reaction). In the first reaction, amination reactions such as the Buchwald–Hartwig reaction can be applied. In the second reaction, tandem hetero-Friedel-Crafts reactions and the like can be applied.

[1495] Hereinafter, specific examples of the compound represented by formula (41) are described, but they 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 methyl and tBu represents tert-butyl.

[1496] [Chemical formula 157]

[1497]

[1498] [Chemical formula 158]

[1499]

[1500] [Chemical formula 159]

[1501]

[1502] [Chemical formula 160]

[1503]

[1504] [Chemical formula 161]

[1505]

[1506] [Chemical formula 162]

[1507]

[1508] [Chemical Formula 163]

[1509]

[1510] [Chemical Formula 164]

[1511]

[1512] [Chemical Formula 165]

[1513]

[1514] [Chemical Formula 166]

[1515]

[1516] [Chemical Formula 167]

[1517]

[1518] [Chemical Formula 168]

[1519]

[1520] [Chemical Formula 169]

[1521]

[1522] [Chemical Formula 170]

[1523]

[1524] [Chemical Formula 171]

[1525]

[1526] (Compound represented by formula (51))

[1527] The compound represented by formula (51) is described below.

[1528] [Chemical Formula 172]

[1529]

[1530] In formula (51),

[1531] ring r is a ring represented by formula (52) or formula (53) fused at any position of adjacent rings.

[1532] ring q and ring s are each independently a ring represented by formula (54) fused at any position of adjacent rings.

[1533] The p-ring and the t-ring are each independently a structure represented by formula (55) or formula (56) fused at any position of adjacent rings.

[1534] R 501 When there are a plurality of them, adjacent plural Rs 501 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.

[1535] X 501 is an oxygen atom, a sulfur atom or NR 502 .

[1536] Rs that do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 501 and R 502 are:

[1537] a hydrogen atom,

[1538] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1539] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1540] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1541] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1542] -Si(R 901 )(R 902 )(R 903 ),

[1543] -O-(R 904 ),

[1544] -S-(R 905 ),

[1545] -N(R 906 )(R 907 ),

[1546] a halogen atom, a cyano group, a nitro group,

[1547] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1548] a monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1549] R 901 ~R 907 are defined as in formula (1) above.

[1550] Ar 501 and Ar502 Each independently is:

[1551] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1552] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1553] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1554] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1555] A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1556] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1557] L 501 Is:

[1558] A substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

[1559] A substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

[1560] A substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

[1561] A substituted or unsubstituted cycloalkylene group having 3 to 50 ring-forming carbon atoms,

[1562] A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or

[1563] A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.

[1564] m1 is each independently an integer of 0 to 2, m2 is each independently an integer of 0 to 4, m3 is each independently an integer of 0 to 3, and m4 is each independently an integer of 0 to 5. R 501 When there are a plurality of them, the plurality of Rs 501 May be the same as or different from each other.

[1565] In formula (51), each of the rings of p-ring to t-ring is fused with an adjacent ring sharing 2 carbon atoms. The position and direction of the fusion are not limited, and it can be fused at any position and direction.

[1566] In one embodiment, in formula (52) or formula (53) of r-ring, R 501 Is a hydrogen atom.

[1567] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-1) to (51-6).

[1568] [Chemical formula 173]

[1569]

[1570] In formulas (51-1) to (51-6), R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1 and m3 are defined as in the aforementioned formula (51).

[1571] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-11) to (51-13).

[1572] [Chemical formula 174]

[1573]

[1574] In formulas (51-11) to (51-13), R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1, m3 and m4 are defined as in the aforementioned formula (51).

[1575] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-21) to (51-25).

[1576] [Chemical formula 175]

[1577]

[1578] In formulas (51-21) to (51-25), R 501 , X 501 , Ar 501 , Ar 502 , L 501 , m1 and m4 are defined as in the aforementioned formula (51).

[1579] In one embodiment, the compound represented by formula (51) is represented by any one of the following formulas (51-31) to (51-33).

[1580] [Chemical formula 176]

[1581]

[1582] In formulas (51-31) to (51-33), R 501 , X 501 , Ar 501 , Ar502 , L 501 , m2 to m4 are defined as in the aforementioned formula (51).

[1583] In one embodiment, Ar 501 and Ar 502 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1584] In one embodiment, one of Ar 501 and Ar 502 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.

[1585] As the compound represented by formula (51), specific examples include the compounds shown below. In the following specific examples, Me represents a methyl group.

[1586] [Chemical formula 177]

[1587]

[1588] [Chemical formula 178]

[1589]

[1590] [Chemical formula 179]

[1591]

[1592] [Chemical formula 180]

[1593]

[1594] [Chemical formula 181]

[1595]

[1596] [Chemical formula 182]

[1597]

[1598] (Compound represented by formula (61))

[1599] The compound represented by formula (61) will be described.

[1600] [Chemical formula 183]

[1601]

[1602] In formula (61),

[1603] R 601 and R 602 , R602 With R 603 , and R 603 With R 604 At least one group among them is bonded to each other to form a divalent group represented by the following formula (62).

[1604] R 605 With R 606 , R 606 With R 607 , and R 607 With R 608 At least one group among them is bonded to each other to form a divalent group represented by the following formula (63).

[1605] [Chemical 184]

[1606]

[1607] R 601 ~R 604 Those among them that do not form the divalent group represented by the aforementioned formula (62), and R 611 ~R 614 At least one of them is a monovalent group represented by the following formula (64).

[1608] R 605 ~R 608 Those among them that do not form the divalent group represented by the aforementioned formula (63), and R 621 ~R 624 At least one of them is a monovalent group represented by the following formula (64).

[1609] X 601 Is an oxygen atom, a sulfur atom or NR 609 .

[1610] R that does not form the divalent groups represented by the aforementioned formulas (62) and (63) and is not the monovalent group represented by the aforementioned formula (64) 601 ~R 608 , R that is not the monovalent group represented by the aforementioned formula (64) 611 ~R 614 And R 621 ~R 624 , And R 609 Are each independently:[[]]

[1611] A hydrogen atom,[[]]

[1612] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,[[]]

[1613] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,[[]]

[1614] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,[[]]

[1615] a cycloalkyl group having 3 to 50 ring carbon atoms, which may be substituted or unsubstituted,

[1616] -Si(R 901 )(R 902 )(R 903 ),

[1617] -O-(R 904 ),

[1618] -S-(R 905 ),

[1619] -N(R 906 )(R 907 ),

[1620] a halogen atom, a cyano group, a nitro group,

[1621] an aryl group having 6 to 50 ring carbon atoms, which may be substituted or unsubstituted, or

[1622] a monovalent heterocyclic group having 5 to 50 ring atoms, which may be substituted or unsubstituted.

[1623] R 901 to R 907 are as defined in the aforementioned formula (1).

[1624] [Chemical 185]

[1625]

[1626] In formula (64), Ar 601 and Ar 602 are each independently:

[1627] an aryl group having 6 to 50 ring carbon atoms, which may be substituted or unsubstituted, or

[1628] a monovalent heterocyclic group having 5 to 50 ring atoms, which may be substituted or unsubstituted.

[1629] L 601 to L 603 are each independently:

[1630] a single bond,

[1631] an arylene group having 6 to 30 ring carbon atoms, which may be substituted or unsubstituted,

[1632] a divalent heterocyclic group having 5 to 30 ring atoms, which may be substituted or unsubstituted, or

[1633] a divalent linking group formed by bonding 2 to 4 of them.

[1634] In formula (61), the positions of the divalent group represented by formula (62) and the divalent group represented by formula (63) are not limited and can form the group at the possible positions of R 601 ~R 608 .

[1635] In one embodiment, the compound represented by formula (61) is represented by any one of the following formulas (61-1) to (61-6).

[1636] [Chemical 186]

[1637]

[1638] In formulas (61-1) to (61-6), X 601 is defined as in the aforementioned formula (61).

[1639] At least two of R 601 ~R 624 are the monovalent groups represented by the aforementioned formula (64).

[1640] R 601 ~R 624 that are not the monovalent groups represented by the aforementioned formula (64) are each independently:

[1641] a hydrogen atom,

[1642] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1643] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1644] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1645] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1646] -Si(R 901 )(R 902 )(R 903 ),

[1647] -O-(R 904 ),

[1648] -S-(R 905 ),

[1649] -N(R 906 )(R 907 ),

[1650] a halogen atom, a cyano group, a nitro group,

[1651] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1652] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[1653] R 901 ~R 907 As defined in the aforementioned formula (1).

[1654] In one embodiment, the compound represented by formula (61) is represented by any one of the following formulas (61-7) to (61-18).

[1655] [Chemical Formula 187]

[1656]

[1657] In formulas (61-7) to (61-18), X 601 As defined in the aforementioned formula (61). * is a single bond bonded to the monovalent group represented by the aforementioned formula (64). R 601 ~R 624 Is the same as R that is not the monovalent group represented by the aforementioned formula (64). 601 ~R 624 Same.

[1658] R that does not form the divalent groups represented by the aforementioned formulas (62) and (63) and is not the monovalent group represented by the aforementioned formula (64), 601 ~R 608 And R that is not the monovalent group represented by the aforementioned formula (64), 611 ~R 614 And R 621 ~R 624 Are preferably each independently:

[1659] A hydrogen atom,

[1660] An alkyl group having 1 to 50 carbon atoms, which may be substituted or unsubstituted,

[1661] An alkenyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1662] An alkynyl group having 2 to 50 carbon atoms, which may be substituted or unsubstituted,

[1663] A cycloalkyl group having 3 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted,

[1664] An aryl group having 6 to 50 ring-forming carbon atoms, which may be substituted or unsubstituted, or

[1665] A monovalent heterocyclic group having 5 to 50 ring-forming atoms, which may be substituted or unsubstituted.

[1666] The monovalent group represented by formula (64) is preferably represented by the following formula (65) or (66).

[1667] [Chemical 188]

[1668]

[1669] In formula (65), R 631 ~R 640 are each independently:

[1670] a hydrogen atom,

[1671] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1672] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1673] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1674] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1675] -Si(R 901 )(R 902 )(R 903 ),

[1676] -O-(R 904 ),

[1677] -S-(R 905 ),

[1678] -N(R 906 )(R 907 ),

[1679] a halogen atom, a cyano group, a nitro group,

[1680] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1681] a monovalent heterocyclic group having 5 to 50 ring atoms, substituted or unsubstituted.

[1682] R 901 ~R 907 are as defined in formula (1) above.

[1683] [Chemical 189]

[1684]

[1685] In formula (66), Ar 601 , L 601 and L 603 are as defined in formula (64) above. HAr 601 has the structure shown in formula (67) below.

[1686] [Chemical 190]

[1687]

[1688] In formula (67), X 602 is an oxygen atom or a sulfur atom.

[1689] R 641 ~R 648 Any one of them is a single bond bonded to L 603 bond.

[1690] R 641 ~R 648 Each independently is:

[1691] A hydrogen atom,

[1692] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1693] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1694] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1695] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1696] -Si(R 901 )(R 902 )(R 903 ),

[1697] -O-(R 904 ),

[1698] -S-(R 905 ),

[1699] -N(R 906 )(R 907 ),

[1700] A halogen atom, a cyano group, a nitro group,

[1701] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1702] A monovalent heterocyclic group having 5 to 50 ring atoms which may be substituted or unsubstituted.

[1703] R 901 ~R 907 Is defined as in the aforementioned formula (1).

[1704] As the compound represented by formula (61), in addition to the compounds described in International Publication No. 2014 / 104144, specific examples such as the following compounds can be cited. In the following specific examples, Me represents a methyl group.

[1705] [Chemical Formula 191]

[1706]

[1707] [Chemical Formula 192]

[1708]

[1709] [Chemical Formula 193]

[1710]

[1711] [Chemical Formula 194]

[1712]

[1713] [Chemical Formula 195]

[1714]

[1715] [Chemical Formula 196]

[1716]

[1717] [Chemical Formula 197]

[1718]

[1719] [Chemical Formula 198]

[1720]

[1721] [Chemical Formula 199]

[1722]

[1723] [Chemical Formula 200]

[1724]

[1725] [Chemical Formula 201]

[1726]

[1727] [Chemical Formula 202]

[1728]

[1729] [Chemical Formula 203]

[1730]

[1731] [Chemical Formula 204]

[1732]

[1733] [Chemical 205]

[1734]

[1735] [Chemical 206]

[1736]

[1737] [Chemical 207]

[1738]

[1739] [Chemical 208]

[1740]

[1741] [Chemical 209]

[1742]

[1743] [Chemical 210]

[1744]

[1745] [Chemical 211]

[1746]

[1747] [Chemical 212]

[1748]

[1749] [Chemical 213]

[1750]

[1751] [Chemical 214]

[1752]

[1753] [Chemical 215]

[1754]

[1755] [Chemical 216]

[1756]

[1757] [Chemical 217]

[1758]

[1759] (Compound represented by formula (71))

[1760] The compound represented by formula (71) will be described.

[1761] [Chemical formula 218]

[1762]

[1763] In formula (71),

[1764] A 701 Ring and A 702 The rings are each independently:

[1765] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or,

[1766] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.

[1767] Selected from A 701 Ring and A 702 One or more of the rings are bonded to the bonding bond * of the structure represented by the following formula (72).

[1768] [Chemical formula 219]

[1769]

[1770] In formula (72),

[1771] A 703 The rings are each independently:

[1772] A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or,

[1773] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.

[1774] X 701 Is NR 703 , C(R 704 )(R 705 ), Si(R 706 )(R 707 ), Ge(R 708 )(R 709 ), O, S or Se.

[1775] R 701 And R 702 Bond to each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1776] R 701 And R 702 That do not form a substituted or unsubstituted saturated or unsaturated ring, and R 703 To R 709 Are each independently:

[1777] a hydrogen atom,

[1778] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1779] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1780] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1781] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,

[1782] -Si(R 901 )(R 902 )(R 903 ),

[1783] -O-(R 904 ),

[1784] -S-(R 905 ),

[1785] -N(R 906 )(R 907 ),

[1786] a halogen atom, a cyano group, a nitro group,

[1787] a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1788] a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be substituted.

[1789] R 901 to R 907 are as defined in the aforementioned formula (1).

[1790] Selected from one or more of the A 701 ring and the A 702 ring are bonded to the bonding bond * of the structure represented by the formula (72). That is, in one embodiment, the A 701 ring's ring-forming carbon atoms of the aforementioned aromatic hydrocarbon ring, or the ring-forming atoms of the aforementioned heterocyclic ring are bonded to the bonding bond * of the structure represented by the formula (72). Further, in one embodiment, the A 702 ring's ring-forming carbon atoms of the aforementioned aromatic hydrocarbon ring, or the ring-forming atoms of the aforementioned heterocyclic ring are bonded to the bonding bond * of the structure represented by the formula (72).

[1791] In one embodiment, the group represented by the following formula (73) is bonded to either or both of the A 701 ring and the A 702 ring.

[1792] [Chemical formula 220]

[1793]

[1794] In formula (73), Ar 701 and Ar 702 are each independently:

[1795] an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted, or

[1796] a monovalent heterocyclic group having 5 to 50 ring-constituting atoms which may be substituted or unsubstituted.

[1797] L 701 to L 703 are each independently:

[1798] a single bond,

[1799] an arylene group having 6 to 30 ring-constituting carbon atoms which may be substituted or unsubstituted,

[1800] a divalent heterocyclic group having 5 to 30 ring-constituting atoms which may be substituted or unsubstituted, or

[1801] a divalent linking group formed by bonding 2 to 4 of them.

[1802] In one embodiment, except for the A 701 ring, the ring-constituting carbon atoms of the aromatic hydrocarbon ring of the A 702 ring or the ring-constituting atoms of the heterocyclic ring are bonded to the bonding bond * of the structure represented by formula (72). At this time, the structures represented by formula (72) may be the same or different.

[1803] In one embodiment, R 701 and R 702 are each independently an aryl group having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted.

[1804] In one embodiment, R 701 and R 702 are bonded to each other to form a fluorene structure.

[1805] In one embodiment, ring A 701 and ring A 702 are aromatic hydrocarbon rings having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted, and for example, are benzene rings which may be substituted or unsubstituted.

[1806] In one embodiment, ring A 703 is an aromatic hydrocarbon ring having 6 to 50 ring-constituting carbon atoms which may be substituted or unsubstituted, and for example, is a benzene ring which may be substituted or unsubstituted.

[1807] In one embodiment, X 701 is O or S.

[1808] As the compound represented by the formula (71), specific examples thereof include the compounds shown below. In the following specific examples, Me represents a methyl group.

[1809] [Chemical formula 221]

[1810]

[1811] [Chemical formula 222]

[1812]

[1813] [Chemical formula 223]

[1814]

[1815] [Chemical formula 224]

[1816]

[1817] (Compound represented by the formula (81))

[1818] The compound represented by the formula (81) will be described.

[1819] [Chemical formula 225]

[1820]

[1821] In the formula (81),

[1822] A 801 The ring is a ring represented by the formula (82) fused at any position of adjacent rings.

[1823] A 802 The ring is a ring represented by the formula (83) fused at any position of adjacent rings. Two bonding bonds * are bonded to any position of the A 803 ring.

[1824] X 801 and X 802 each independently represents C(R 803 )(R 804 ), Si(R 805 )(R 806 ), an oxygen atom, or a sulfur atom.

[1825] A 803 The ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms.

[1826] Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

[1827] R 801 ~R 806 Each independently is:

[1828] A hydrogen atom,

[1829] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1830] A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1831] A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1832] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1833] -Si(R 901 )(R 902 )(R 903 ),

[1834] -O-(R 904 ),

[1835] -S-(R 905 ),

[1836] -N(R 906 )(R 907 ),

[1837] A halogen atom, a cyano group, a nitro group,

[1838] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1839] A monovalent heterocyclic group having 5 to 50 ring atoms which may be substituted or unsubstituted.

[1840] R 901 ~R 907 Is as defined in the aforementioned formula (1).

[1841] m801 and m802 are each independently an integer of 0 to 2. When they are 2, multiple Rs 801 or R 802 May be the same or different from each other.

[1842] a801 is an integer of 0 to 2. When a801 is 0 or 1, the structures within the parentheses indicated by "3 - a801" may be the same or different from each other. When a801 is 2, Ar 801 May be the same or different from each other.

[1843] In one embodiment, Ar 801 Is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1844] In one embodiment, ring A 803 is an aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms which is substituted or unsubstituted, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

[1845] In one embodiment, R 803 and R 804 are each independently an alkyl group having 1 to 50 carbon atoms which is substituted or unsubstituted.

[1846] In one embodiment, a801 is 1.

[1847] As the compound represented by formula (81), specific examples thereof include the compounds shown below.

[1848] [Chemical formula 226]

[1849]

[1850] Specific examples of each group such as formula (A1) to (D1) are described in the [Definition] section of this specification.

[1851] (Compound represented by formula (91))

[1852] The compound represented by formula (91) will be described.

[1853] [Chemical formula 227]

[1854]

[1855] In formula (91),

[1856] R 951 to R 960 in any one or more groups of two or more adjacent to each other, R a1 to R a5 in any one or more groups of two or more adjacent to each other, and R a6 to R a10 in any one or more groups of two or more adjacent to each other are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring-forming atoms which is substituted or unsubstituted.

[1857] R 951 to R 960 , R a1 to R a5 , and R a6 to R a10 which do not participate in the ring formation are each independently:

[1858] a hydrogen atom,

[1859] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1860] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[1861] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1862] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[1863] a substituted or unsubstituted amino group,

[1864] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1865] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[1866] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[1867] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[1868] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[1869] a substituted or unsubstituted phosphino group,

[1870] a substituted or unsubstituted phosphoryl group,

[1871] a substituted or unsubstituted silyl group,

[1872] a substituted or unsubstituted arylcarbonyl group having 6 to 30 ring carbon atoms,

[1873] Cyano, nitro, carboxyl, or

[1874] Halogen atoms.

[1875] R 951 ~R 956 , R 957 ~R 960 , R a1 ~R a5 , and R a6 ~R a10 At least one group of any two or more adjacent ones of are bonded to each other to form a ring.

[1876] Regarding “R 951 ~R 960 One or more sets of two or more adjacent ones, R a1 ~R a5 One or more sets of two or more adjacent ones, and R a6 ~R a10Specific examples of "one or more groups of two or more adjacent to each other" that are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring-forming atoms, which may be substituted or unsubstituted, will be described.

[1877] As a specific example of two or more adjacent to each other that are bonded to each other to form a ring, if R in the above formula (91) 957 ~R 960 is taken as an example, partial structures such as the following can be cited. In the following partial structures, R 958 、R 959 and R 960 are bonded to each other to form a ring.

[1878] [Chemical formula 228]

[1879]

[1880] In addition, as a specific example of "one or more groups of two or more adjacent to each other" that are bonded to each other to form a ring, if R in the above formula (91) 951 ~R 956 is taken as an example, partial structures such as the following can be cited. In the following partial structures, R 952 and R 953 、and R 954 and R 955 are bonded to each other to form another two rings.

[1881] [Chemical formula 229]

[1882]

[1883] In one embodiment, R in the above formula (91) 952 and R 953 are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring-forming atoms, which may be substituted or unsubstituted.

[1884] In one embodiment, the compound represented by the above formula (91) is the compound represented by the following formula (91-1).

[1885] [Chemical formula 230]

[1886]

[1887] In formula (91-1), R 951 、R 954 ~R 960 are defined as in the above formula (91).

[1888] R c1 and R c2 are each independently:

[1889] a hydrogen atom,

[1890] An unsubstituted alkyl group having 1 to 50 carbon atoms,

[1891] An unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1892] An unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1893] An unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1894] -Si(R 901 )(R 902 )(R 903 ),

[1895] -O-(R 904 ),

[1896] -S-(R 905 ),

[1897] -N(R 906 )(R 907 ),

[1898] A halogen atom, a cyano group, a nitro group,

[1899] An unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1900] A monovalent heterocyclic group having 5 to 50 ring atoms and being unsubstituted.

[1901] R 901 to R 907 are each independently:

[1902] A hydrogen atom,

[1903] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1904] A substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1905] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1906] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When there are two or more R 901 to R 907 two or more R 901 to R 907 may be the same or different from each other.

[1907] In one embodiment, R 958 to R 960Two or more of them are bonded to each other to form a saturated or unsaturated ring having 3 to 30 ring-forming atoms, which may be substituted or unsubstituted.

[1908] In one embodiment, the compound represented by the aforementioned formula (91) is a compound represented by the following formula (91-2).

[1909] [Chemical formula 231]

[1910]

[1911] In formula (91-2), R 951 ~R 957 are as defined in the aforementioned formula (91).

[1912] In one embodiment, R 951 ~R 960 , R a1 ~R a5 , and R a6 ~R a10 not participating in ring formation in the aforementioned formula (91) are each independently:

[1913] a hydrogen atom,

[1914] an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or

[1915] a monovalent heterocyclic group having 5 to 50 ring-forming atoms which may be unsubstituted.

[1916] Hereinafter, although specific examples of the compound represented by formula (91) are described, they are merely illustrative, and the compound represented by formula (91) is not limited to the following specific examples.

[1917] [Chemical formula 232]

[1918]

[1919] [Chemical formula 233]

[1920]

[1921] [Chemical formula 234]

[1922]

[1923] [Chemical formula 235]

[1924]

[1925] [Chemical formula 236]

[1926]

[1927] [Chemical formula 237]

[1928]

[1929] [Chemical formula 238]

[1930]

[1931] [Chemical formula 239]

[1932]

[1933] [Chemical formula 240]

[1934]

[1935] [Chemical formula 241]

[1936]

[1937] [Chemical formula 242]

[1938]

[1939] [Chemical formula 243]

[1940]

[1941] [Chemical formula 244]

[1942]

[1943] [Chemical formula 245]

[1944]

[1945] [Chemical formula 246]

[1946]

[1947] [Chemical formula 247]

[1948]

[1949] [Chemical formula 248]

[1950]

[1951] [Chemical formula 249]

[1952]

[1953] [Chemical formula 250]

[1954]

[1955] [Chemical formula 251]

[1956]

[1957] [Chemical formula 252]

[1958]

[1959] [Chemical formula 253]

[1960]

[1961] [Chemical formula 254]

[1962]

[1963] An organic EL element according to one embodiment of the present invention, as described above, has:

[1964] an anode,

[1965] a cathode, and

[1966] a light-emitting region located between the aforementioned anode and the aforementioned cathode,

[1967] the aforementioned light-emitting region includes a first light-emitting layer and a second light-emitting layer,

[1968] the aforementioned first light-emitting layer and the aforementioned second light-emitting layer are directly adjacent to each other,

[1969] the aforementioned first light-emitting layer is located between the aforementioned anode and the aforementioned second light-emitting layer,

[1970] Either the aforementioned first light-emitting layer or the aforementioned second light-emitting layer, in addition to containing a compound having at least one deuterium atom, as long as the effects of the present invention are not impaired, known materials and element configurations in the past can be applied.

[1971] Hereinafter, the layer configuration of an organic EL element according to one embodiment of the present invention will be described.

[1972] An organic EL element according to one embodiment of the present invention has an organic layer between a pair of electrodes composed of a cathode and an anode. The organic layer is laminated with a plurality of layers containing organic compounds. The organic layer may have a layer formed of only one or more organic compounds. The organic layer may have a layer containing both an organic compound and an inorganic compound. The organic EL element may have a layer formed of only one or more inorganic compounds.

[1973] The layers that can be adopted in the layer configuration of the organic EL element are not particularly limited, and examples thereof include a hole transport 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 region (electron transport layer, electron injection layer, hole blocking layer, etc.) provided between the cathode and the light-emitting layer, and the like.

[1974] The organic EL element according to one embodiment of the present invention may be, for example, a monochromatic light-emitting element of fluorescence or phosphorescence light emission type, or may be a white light-emitting element of fluorescence / phosphorescence hybrid type. Further, it may be a single type having a single light-emitting unit, or may be a series type having a plurality of light-emitting units.

[1975] It should be noted that the "light-emitting unit" means the minimum unit that contains an organic layer, at least one layer of which is a light-emitting layer and emits light by recombination of injected holes and electrons.

[1976] In addition, the "light-emitting layer" described in this specification means an organic layer having a light-emitting function. The light-emitting layer may be, for example, a phosphorescent light-emitting layer, a fluorescent light-emitting layer, etc., and may be one layer or a plurality of layers.

[1977] 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 for preventing excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer may be provided between the respective light-emitting layers.

[1978] As a single-type organic EL element, for example, an element configuration of anode / light-emitting unit / cathode can be cited.

[1979] A representative layer configuration of the light-emitting unit is shown below. The layers in parentheses are optional.

[1980] (c) (Hole injection layer / ) Hole transport layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer ( / Electron transport layer / Electron injection layer)

[1981] (d) (Hole injection layer / ) Hole transport layer / First phosphorescent light-emitting layer / Second phosphorescent light-emitting layer ( / Electron transport layer / Electron injection layer)

[1982] (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)

[1983] (h) (Hole injection layer / ) Hole transport layer / Phosphorescent light-emitting layer / Spacer layer / First fluorescent light-emitting layer / Second fluorescent light-emitting layer ( / Electron transport layer / Electron injection layer)

[1984] (i) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Fluorescent light-emitting layer / Fluorescent light-emitting layer ( / Electron transport layer / Electron injection layer)

[1985] (j) (Hole injection layer / ) Hole transport layer / Electron blocking layer / Phosphorescent light-emitting layer / Phosphorescent light-emitting layer ( / Electron transport layer / Electron injection layer)

[1986] (k) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Fluorescent emission layer / Fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[1987] (l) (Hole injection layer / ) Hole transport layer / Exciton blocking layer / Phosphorescent emission layer / Phosphorescent emission layer ( / Electron transport layer / Electron injection layer)

[1988] (m) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer / Fluorescent emission layer ( / Electron transport layer / Electron injection layer)

[1989] (n) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Fluorescent emission layer / Fluorescent emission layer ( / First electron transport layer / Second electron transport layer / Electron injection layer)

[1990] (o) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emission layer / Phosphorescent emission layer ( / Electron transport layer / Electron injection layer)

[1991] (p) (Hole injection layer / ) First hole transport layer / Second hole transport layer / Phosphorescent emission layer / Phosphorescent emission layer ( / First electron transport layer / Second electron transport layer / Electron injection layer)

[1992] (q) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Fluorescent emission layer / Hole blocking layer ( / Electron transport layer / Electron injection layer)

[1993] (r) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Phosphorescent emission layer / Hole blocking layer ( / Electron transport layer / Electron injection layer)

[1994] (s) (Hole injection layer / ) Hole transport layer / Fluorescent emission layer / Fluorescent emission layer / Exciton blocking layer ( / Electron transport layer / Electron injection layer)

[1995] (t) (Hole injection layer / ) Hole transport layer / Phosphorescent emission layer / Phosphorescent emission layer / Exciton blocking layer ( / Electron transport layer / Electron injection layer)

[1996] Herein, the layer structure of the organic EL element of one embodiment of the present invention is not limited thereto. For example, when the organic EL element has a hole injection layer and a hole transport layer, it is preferable to provide a hole injection layer 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, it is preferable to provide an electron injection layer between the electron transport layer and the cathode. In addition, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of one layer or multiple layers.

[1997] A plurality of phosphorescent light-emitting layers, and the phosphorescent light-emitting layer and the fluorescent light-emitting layer can each be a light-emitting layer with a different color. For example, the aforementioned light-emitting unit (f) can be a hole transport layer / first phosphorescent light-emitting layer (red light emission) / second phosphorescent light-emitting layer (green light emission) / spacer layer / fluorescent light-emitting layer (blue light emission) / electron transport layer.

[1998] It should be noted that an electron blocking layer can be provided between each light-emitting layer and the hole transport layer or the spacer layer. In addition, a hole blocking layer can be provided between each light-emitting layer and the electron transport layer. Through the electron blocking layer and the hole blocking layer, electrons or holes can be confined within the light-emitting layer, increasing the recombination probability of charges in the light-emitting layer and improving the light-emitting efficiency.

[1999] As a representative element configuration of the tandem organic EL element, for example, an element configuration such as an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode can be cited.

[2000] The first light-emitting unit and the second light-emitting unit can each be independently selected from the above-mentioned light-emitting units, for example.

[2001] The intermediate layer is usually also referred to as an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, connector layer, or 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.

[2002] Hereinafter, the functions and materials of each layer of the organic EL element described in this specification will be described.

[2003] (Substrate)

[2004] The substrate serves as a support for the organic EL element. The substrate preferably has a light transmittance of 50% or more in the visible light region of wavelengths 400 to 700 nm, and is also preferably a smooth substrate. Examples of the material of the substrate include soda-lime glass, aluminosilicate glass, quartz glass, plastics, etc. In addition, as the substrate, a flexible substrate can be used. A flexible substrate refers to a substrate that can be bent (flexible), and examples include plastic substrates, etc. Specific examples of the material for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, etc. In addition, an inorganic vapor deposition film can also be used.

[2005] (Anode)

[2006] As the anode, those with a large work function (specifically, 4.0 eV or more), such as metals, alloys, conductive compounds, and mixtures thereof, are preferably used. Specific examples of the material for the anode include indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium 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 (for example, titanium nitride), etc. can also be cited.

[2007] The anode can generally be formed by depositing 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 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.

[2008] As other formation methods for the anode, for example, vacuum evaporation, coating, inkjet, spin coating, etc. can be cited. For example, when using silver paste, etc., coating, inkjet, etc. can be used.

[2009] It should be noted that the hole injection layer formed in contact with the anode is formed using a material that is independent of the work function of the anode and is easy to inject holes. Therefore, the anode can use ordinary electrode materials, such as metals, alloys, conductive compounds, and mixtures thereof. Specifically, alkali metals such as lithium and cesium; magnesium; alkaline earth metals such as calcium and strontium; alloys containing these metals (for example, magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium; alloys containing rare earth metals, etc., materials with a small work function can also be used for the anode.

[2010] (Hole injection layer)

[2011] The hole injection layer is a layer containing a substance with high hole injection properties and has the function of injecting holes from the anode into the organic layer. As substances with high hole injection properties, 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 and acceptor compounds are preferred, and acceptor compounds are more preferred.

[2012] As specific examples of the aromatic amine compound, 4,4’,4”-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4’,4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4’-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4’-bis(N-{4-[N’-(3-methylphenyl)-N’-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), etc. can be cited.

[2013] As the acceptor compound, a heterocyclic derivative having an electron-withdrawing group, a quinone derivative having an electron-withdrawing group, an arylborane derivative, a heteroarylborane derivative, etc. are preferably used. As specific examples, 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. can be cited.

[2014] When using the acceptor compound, the hole injection layer preferably further contains a matrix material. As the matrix material, a material known as a material for an organic EL element can be used, and a donating (donor) compound is preferably used, for example.

[2015] (Hole transport layer)

[2016] The hole transport layer is a layer containing a substance having a high hole transport property and has a function of transporting holes from the anode to the organic layer.

[2017] As the substance having a high hole transport property, a substance having a hole mobility of 10 -6 cm 2 / (V・s) or more is preferably used. For example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymer compounds, etc. can be cited.

[2018] As specific examples of the aromatic amine compounds, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), etc. can be cited.

[2019] As specific examples of the carbazole derivatives, 4,4'-bis(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA), etc. can be cited.

[2020] As specific examples of the anthracene derivatives, 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-bis(2-naphthyl)anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), etc. can be cited.

[2021] As specific examples of the high molecular compounds, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), etc. can be cited.

[2022] As long as the compound has a higher hole transport property than the electron transport property, a substance other than the above can also be used for the hole transport layer.

[2023] The hole transport layer can be a single layer or two or more layers can be stacked. In this case, it is preferable to dispose a layer containing a substance having a larger energy gap among the substances having a high hole transport property on the side closer to the light emitting layer.

[2024] (Light emitting layer)

[2025] The light-emitting layer is a layer containing a substance with high luminescence (dopant material). As the dopant material, various materials can be used. For example, fluorescent luminescent compounds (fluorescent dopants), phosphorescent luminescent compounds (phosphorescent dopants), etc. can be used. A fluorescent luminescent compound is a compound that can emit light from a singlet excited state, and the light-emitting layer containing it is called a fluorescent light-emitting layer. In addition, a phosphorescent luminescent compound is a compound that can emit light from a triplet excited state, and the light-emitting layer containing it is called a phosphorescent light-emitting layer.

[2026] The light-emitting layer usually contains a dopant material and a host material for efficient light emission. It should be noted that the dopant material is sometimes also called the guest material, emitter, or luminescent material depending on the literature. In addition, the host material is sometimes also called the matrix material depending on the literature.

[2027] A light-emitting layer can contain multiple dopant materials and multiple host materials. In addition, the light-emitting layer can be multilayered.

[2028] 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 distinguished only by the molecular structure. The phosphorescent host is a material for forming 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 applies to the fluorescent host.

[2029] The content of the dopant material in the light-emitting layer is not particularly limited. From the viewpoints of sufficient light emission and concentration quenching, for example, it is preferably 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, further preferably 1 to 30% by mass, still further preferably 1 to 20% by mass, and particularly preferably 1 to 10% by mass.

[2030] <Fluorescent dopant>

[2031] Examples of the fluorescent dopant include, for example, fused polycyclic aromatic derivatives, styrylamine derivatives, condensed ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc. Among them, condensed ring amine derivatives, boron-containing compounds, and carbazole derivatives are preferred.

[2032] Examples of the condensed ring amine derivatives include, for example, diamino pyrene derivatives, diamino chrysene derivatives, diamino anthracene derivatives, diamino fluorene derivatives, diamino fluorene derivatives obtained by fusing one or more benzofuran skeletons, etc.

[2033] Examples of the boron-containing compounds include, for example, pyrromethene derivatives, triphenylborane derivatives, etc.

[2034] Examples of the fluorescent dopants in the blue color system include, for example, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include: N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenyldistyrene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc.

[2035] Examples of the fluorescent dopants in the green color system include, for example, aromatic amine derivatives, etc. Specific examples include: N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), etc.

[2036] Examples of the fluorescent dopants in the red color system include perylene derivatives, diamine derivatives, etc. Specific examples include: N,N,N',N'-tetrakis(4-methylphenyl)perylene-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.

[2037] <Phosphorescent dopant>

[2038] Examples of the phosphorescent dopants include, for example, phosphorescent heavy metal complexes and phosphorescent rare earth metal complexes.

[2039] Examples of the heavy metal complexes include, for example, iridium complexes, osmium complexes, platinum complexes, etc. The heavy metal complexes are preferably orthometalated complexes of metals selected from iridium, osmium, and platinum.

[2040] Examples of the rare earth metal complexes include, for example, terbium complexes, europium complexes, etc. Specifically, examples include: tris(acetylacetonato)(1,10-phenanthroline)terbium(III) (abbreviation: Tb(acac) 3 (Phen)), tris(1,3-diphenyl-1,3-propanedionato)(1,10-phenanthroline)europium(III) (abbreviation: Eu(DBM) 3 (Phen)), tris[1-(2-thienoyl)-3,3,3-trifluoroacetonato](1,10-phenanthroline)europium(III) (abbreviation: Eu(TTA) 3 (Phen)), etc. Since these rare earth metal complexes emit light due to the electron transfer between different multiplets of the rare earth metal ions, they are preferably used as phosphorescent dopants.

[2041] Examples of the blue phosphorescent dopants include, for example, iridium complexes, osmium complexes, platinum complexes, etc. Specifically, examples include: bis[2-(4’,6’-difluorophenyl)pyridine-N,C2’]tetrakis(1-pyrazolyl)boratoiridium(III) (abbreviation: FIr6), bis[2-(4’,6’-difluorophenyl)pyridine-N,C2’]picolinatoiridium(III) (abbreviation: FIrpic), bis[2-(3’,5’-bis(trifluoromethyl)phenyl)pyridine-N,C2’]picolinatoiridium(III) (abbreviation: Ir(CF3ppy) 2 (pic)), bis[2-(4’,6’-difluorophenyl)pyridine-N,C2’]acetylacetonatoiridium(III) (abbreviation: FIrracac), etc.

[2042] Examples of the green phosphorescent dopants include, for example, iridium complexes, etc. Specifically, examples include: tris(2-phenylpyridine-N,C2’)iridium(III) (abbreviation: Ir(ppy) 3 )), bis(2-phenylpyridine-N,C2’)acetylacetonatoiridium(III) (abbreviation: Ir(ppy) 2 (acac)), bis(1,2-diphenyl-1H-benzoimidazole)acetylacetonatoiridium(III) (abbreviation: Ir(pbi) 2 (acac)), bis(benzo[h]quinoline)acetylacetonatoiridium(III) (abbreviation: Ir(bzq) 2 (acac)), etc.

[2043] Examples of the red phosphorescent dopants include, for example, iridium complexes, platinum complexes, terbium complexes, europium complexes, etc. Specifically, examples include: bis[2-(2’-benzo[4,5-α]thienyl)pyridine-N,C3’]acetylacetonatoiridium(III) (abbreviation: Ir(btp) 2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq) 2 (acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviation: Ir(Fdpq) 2 (acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP), etc.

[2044] <Host material>

[2045] Examples of the host material include, 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. Multiple host materials can be used in combination.

[2046] Specific examples of the metal complex include: tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ), etc.

[2047] Specific examples of the heterocyclic compound 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-biphenyl)-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), bathocuproine (abbreviation: BCP), etc.

[2048] As specific examples of the fused aromatic compounds, the following can be mentioned: 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,9'-bianthracene (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, etc.

[2049] As specific examples of the aromatic amine compounds, the following can be mentioned: N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB), etc.

[2050] As the fluorescent host, a compound having a singlet energy level higher than that of the fluorescent dopant is preferred, and examples thereof include heterocyclic compounds, fused aromatic compounds, etc. As the fused aromatic compound, anthracene derivatives, pyrene derivatives, chrysene derivatives, tetracene derivatives, etc. are preferred.

[2051] As a phosphorescent host, a compound having a triplet energy level higher than that of the phosphorescent dopant is preferred. Examples thereof include metal complexes, heterocyclic compounds, fused 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.

[2052] (Electron transport layer)

[2053] The electron transport layer is a layer containing a substance with high electron transportability. As the substance with high electron transportability, a substance having an electron mobility of 10 -6 cm 2 / Vs or more is preferred. Examples thereof include metal complexes, aromatic heterocyclic compounds, aromatic hydrocarbon compounds, polymer compounds, etc.

[2054] Examples of the metal complex include aluminum complex, beryllium complex, zinc complex, etc. Specifically, tris(8-hydroxyquinoline)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviation: BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviation: BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviation: ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviation: ZnBTZ), etc. can be cited.

[2055] As the aromatic heterocyclic compound, for example, imidazole derivatives such as benzimidazole derivatives, imidazopyridine derivatives, benzimidazophenanthridine derivatives, etc.; pyrazine derivatives such as pyrimidine derivatives, triazine derivatives, etc.; compounds containing a nitrogen-containing six-membered ring structure such as quinoline derivatives, isoquinoline derivatives, phenanthroline derivatives, etc. (also including those having a phosphine oxide-based substituent on the heterocycle), etc. Specifically, 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), bathocuproine (abbreviation: BCP), 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs), etc. can be cited.

[2056] As the aromatic hydrocarbon compound, for example, anthracene derivatives, fluoranthene derivatives, etc. can be cited.

[2057] As a specific example of the high molecular compound, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy), etc. can be cited.

[2058] As long as the compound has higher electron transport property than hole transport property, a substance other than the above can also be used for the electron transport layer.

[2059] The electron transport layer can be a single layer or can be laminated with two or more layers. At this time, it is preferable to dispose a layer containing a substance having a relatively large energy gap among substances having high electron transport property on the side closer to the light-emitting layer.

[2060] The electron transport layer can contain, for example, metals such as alkali metals, magnesium, alkaline earth metals, alloys containing two or more of them; metal compounds such as lithium 8-hydroxyquinoline (abbreviation: Liq) and alkaline earth metal compounds. When a metal such as an alkali metal, magnesium, alkaline earth metal, or an alloy containing two or more of them is contained in the electron transport layer, its content is not particularly limited, and it is preferably 0.1 to 50% by mass, more preferably 0.1 to 20% by mass, and further preferably 1 to 10% by mass.

[2061] 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. It should be noted that the layer on the light-emitting layer side when the electron transport layer is a multilayer can be formed only of these metal compounds.

[2062] (Electron injection layer)

[2063] 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. Examples of substances with high electron injection property include alkali metals, magnesium, alkaline earth metals, and their compounds. Specific examples include: lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, lithium oxide, etc. In addition, a substance obtained by containing an alkali metal, magnesium, alkaline earth metal, or their compound in a substance with electron transport property can be used. For example, a substance obtained by containing magnesium in Alq can be used.

[2064] In addition, a composite material containing an organic compound and a donor compound can also be used for the electron injection layer. Since the organic compound receives electrons from the donor compound, such a composite material has excellent electron injection property and electron transport property.

[2065] As the organic compound, a substance with excellent electron transport property for received electrons is preferred. For example, the above-mentioned substances with high electron transport property, namely, metal complexes, aromatic heterocyclic compounds, etc., can be used.

[2066] As the donor compound, any substance that can supply electrons to the organic compound can be used. Examples include alkali metals, magnesium, alkaline earth metals, rare earth metals, etc. Specific examples include: lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. In addition, alkali metal oxides and alkaline earth metal oxides are preferred. Specific examples include: lithium oxide, calcium oxide, barium oxide, etc. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

[2067] (Cathode)

[2068] The cathode preferably uses a metal, alloy, conductive compound, and their mixture 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 (e.g., magnesium-silver, aluminum-lithium); rare earth metals such as europium and ytterbium; alloys containing rare earth metals, etc.

[2069] The cathode is usually formed by vacuum evaporation, sputtering. In addition, when using silver paste, etc., coating methods, inkjet methods, etc. can be used.

[2070] In addition, when an electron injection layer is provided, regardless of the work function, various conductive materials such as aluminum, silver, ITO, graphene, indium tin oxide containing silicon or silicon oxide, etc. can be used to form the cathode. These conductive materials can be formed into a film by sputtering, inkjet printing, spin coating, etc.

[2071] (Insulating layer)

[2072] For an organic EL element, since an electric field is applied to a thin film, pixel defects due to leakage and short circuit are likely to occur. To prevent this phenomenon, a thin film insulating layer can be inserted between a pair of electrodes.

[2073] Specific examples of the substance used as 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 can also use a mixture thereof. In addition, it can be made into a laminate of multiple layers containing these substances.

[2074] (Spacer layer)

[2075] For the spacer layer, for example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are stacked, it can be provided between the two layers in order 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 can also be provided between multiple phosphorescent light-emitting layers, etc.

[2076] Since the spacer layer is provided between multiple light-emitting layers, it is preferably formed of a substance having both electron-transporting properties and hole-transporting properties. In addition, from the viewpoint of preventing the diffusion of triplet energy in adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or more.

[2077] As the substance for the spacer layer, those same as the substances for the hole-transporting layer described above can be cited.

[2078] (Electron blocking layer, hole blocking layer, exciton blocking layer)

[2079] An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, etc. can be provided adjacent to the light-emitting layer.

[2080] The electron blocking layer is a layer having a function of blocking electrons from leaking from the light-emitting layer to the hole-transporting layer. The hole blocking layer is a layer having a function of blocking holes from leaking from the light-emitting layer to the electron-transporting layer. The exciton blocking layer is a layer having a function of blocking excitons generated in the light-emitting layer from diffusing into adjacent layers and confining the excitons within the light-emitting layer.

[2081] (Intermediate layer)

[2082] An intermediate layer is provided in the tandem organic EL element.

[2083] (Layer formation method)

[2084] Unless otherwise specified, the method for forming each layer of the organic EL element is not particularly limited. As the formation method, known methods such as dry film formation methods and wet film formation methods can be used. Specific examples of dry film formation methods include vacuum evaporation, sputtering, plasma, ion plating, etc. Specific examples of wet film formation methods include various coating methods such as spin coating, dipping, flow coating, and inkjet printing.

[2085] (Film thickness)

[2086] Unless otherwise specified, the film thickness of each layer of the organic EL element is not particularly limited. If the film thickness is too small, defects such as pinholes are likely to occur, and sufficient emission luminance cannot be obtained. On the other hand, if the film thickness is too large, a large driving voltage is required and the efficiency is reduced. From this point of view, the film thickness is usually preferably 1 nm to 10 μm, more preferably 1 nm to 0.2 μm.

[2087] [Electronic device]

[2088] The electronic device according to one embodiment of the present invention includes the organic EL element according to one embodiment of the present invention described above. Specific examples of the electronic device include display components such as organic EL panel assemblies; display devices such as televisions, mobile phones, smartphones, and personal computers; light-emitting devices such as lighting and vehicle lamps. Examples

[2089] Next, examples and comparative examples are given to further illustrate the present invention in detail, but the present invention is not limited by the content described in these examples in any way.

[2090] <Compound>

[2091] The compounds (host materials) represented by formula (1) having deuterium atoms used in the production of the organic EL elements of Examples 1 to 42 are as follows.

[2092] [Chemical formula 255]

[2093]

[2094] The compounds (host materials) not having deuterium atoms used in the production of the organic EL elements of Examples 1 to 42 and Comparative Examples 1 to 15 are as follows.

[2095] [Chemical formula 256]

[2096]

[2097] The dopant materials used in the production of the organic EL elements of Examples 1 to 42 and Comparative Examples 1 to 15 are as follows.

[2098] [Chemical formula 257]

[2099]

[2100] Other compounds used in the production of the organic EL elements of Examples 1 to 42 and Comparative Examples 1 to 15 are as follows.

[2101] [Chemical formula 258]

[2102]

[2103] <Fabrication 1 of Organic EL Element>

[2104] The organic EL element was fabricated and evaluated as described below.

[2105] Example 1

[2106] A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The film thickness of ITO was 130 nm.

[2107] The cleaned glass substrate with the transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, on the surface where the transparent electrode was formed, compound HI was evaporated in a manner to cover the transparent electrode, forming a compound HI film with a thickness of 5 nm. This HI film functions as a hole injection layer.

[2108] After forming this HI film, compound HT was then evaporated to form an HT film with a thickness of 80 nm on the HI film. This HT film functions as the first hole transport layer.

[2109] After forming the HT film, compound EBL was then evaporated to form an EBL film with a thickness of 10 nm on the HT film. This EBL film functions as the second hole transport layer.

[2110] On the EBL film, D-BH-1 (host material) and BD-1 (dopant material) were co-evaporated so that the ratio (mass ratio) of BD-1 reached 4%, forming a first light-emitting layer with a thickness of 7.5 nm.

[2111] On the first light-emitting layer, BH-1 (host material) and BD-1 (dopant material) were co-evaporated so that the ratio (mass ratio) of BD-1 reached 4%, forming a second light-emitting layer with a thickness of 17.5 nm.

[2112] An HBL is vapor-deposited on the second light-emitting layer to form an electron transport layer with a film thickness of 10 nm. An ET, which is an electron injection material, is vapor-deposited on the electron transport layer to form an electron injection layer with a film thickness of 15 nm. LiF is vapor-deposited on the electron injection layer to form a LiF film with a film thickness of 1 nm. Metal Al is vapor-deposited on the LiF film to form a metal cathode with a film thickness of 80 nm.

[2113] The organic EL element is fabricated as described above. The layer structure of the element is as follows.

[2114] ITO (130 nm) / HI (5 nm) / HT (80 nm) / EBL (10 nm) / D-BH-1:BD-1 (7.5 nm:4%) / BH-1:BD-1 (17.5 nm:4%) / HBL (10 nm) / ET (15 nm) / LiF (1 nm) / Al (80 nm)

[2115] In the parentheses, the numbers represented as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2116] (Evaluation 1 of the organic EL element)

[2117] For the obtained organic EL element, a voltage is applied such that the current density reaches 50 mA / cm 2 , and the time (LT90 (unit: hours)) until the luminance reaches 90% of the initial luminance is measured. The results are shown in Table 1.

[2118] Comparative Example 1

[2119] An organic EL element is fabricated and evaluated in the same manner as in Example 1, except that the compound shown in Table 1 is used as the host material of the light-emitting layer. The results are shown in Table 1.

[2120] [Table 1]

[2121]

[2122] Example 2 and Comparative Example 2

[2123] An organic EL element is fabricated and evaluated in the same manner as in Example 1, except that the compound shown in Table 2 is used as the host material of the light-emitting layer. The results are shown in Table 2.

[2124] [Table 2]

[2125]

[2126] As can be seen from the results of Table 1 and Table 2, in Examples 1 and 2 where a first light-emitting layer containing a host material having deuterium atoms and a second light-emitting layer containing a host material not having deuterium atoms are stacked in the light-emitting region, the lifetime of the elements is improved compared to the elements of Comparative Examples 1 and 2 having a single light-emitting layer containing a host material not having deuterium atoms.

[2127] The light-emitting layers of Examples 1 and 2 and the light-emitting layers of Comparative Examples 1 and 2 have the same thickness when viewed as a whole for the light-emitting layer. From this, it can be seen that even if the entire region of the light-emitting region does not contain a host material having deuterium atoms, i.e., D-BH-1 and D-BH-2, as long as a part of the light-emitting layer in the light-emitting region contains a host material having deuterium atoms, i.e., D-BH-1 and D-BH-2, the lifetime is also improved.

[2128] <Fabrication of Organic EL Element 2>

[2129] Example 3

[2130] A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO (Indium Tin Oxide) transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of the ITO transparent electrode was made 130 nm.

[2131] The cleaned glass substrate with the transparent electrode line was mounted on the substrate holder of a vacuum evaporation apparatus. First, on the surface on which the transparent electrode line was formed, Compound HA1 was evaporated to cover the transparent electrode, forming a hole injection layer (HI) with a film thickness of 5 nm.

[2132] After the formation of the hole injection layer, Compound HT1 was then evaporated to form a first hole transport layer (HT) with a film thickness of 80 nm.

[2133] After the formation of the first hole transport layer, Compound HT2 was then evaporated to form a second hole transport layer (also referred to as an electron barrier layer) (EBL) with a film thickness of 10 nm.

[2134] On the second hole transport layer, Compound D-BH-1 (first host material (BH)) and Compound BD-2 (dopant material (BD)) were co-evaporated so that the proportion of Compound BD-2 reached 4 mass%, forming a first light-emitting layer with a film thickness of 10 nm.

[2135] On the first light-emitting layer, Compound BH-3 (second host material (BH)) and Compound BD-2 (dopant material (BD)) were co-evaporated so that the proportion of Compound BD-2 reached 2 mass%, forming a second light-emitting layer with a film thickness of 15 nm.

[2136] Compound ET1 was evaporated on the second light-emitting layer to form an electron transport layer with a film thickness of 10 nm.

[2137] Compound nCGL and metal Li were co-evaporated on the electron transport layer to form an electron injection layer with a film thickness of 30 nm such that the proportion of metal Li reached 4% by mass.

[2138] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 50 nm.

[2139] The element structure of Example 3 is briefly shown below.

[2140] ITO(130) / HA1(5) / HT1(80) / HT2(10) / D-BH-1:BD-2(10, 98%:2%) / BH-3:BD-2(15, 98%:2%) / ET1(10) / nCGL:Li(30, 96%:4%) / Al(50))

[2141] It should be noted that the numbers in parentheses represent the film thickness (unit: nm).

[2142] Similarly, within the parentheses, the numbers expressed as percentages (98%:2%) represent the proportion (by mass) of the first host material (compound BH1 or compound BH2) and compound BD1 in the first and second light-emitting layers, and the numbers expressed as percentages (96%:4%) represent the proportion (by mass) of compound nCGL and metal Li in the hole injection layer. The same expression will be used hereinafter.

[2143] Example 4

[2144] The organic EL element of Example 4 was fabricated in the same manner as Example 3, except that the first and second light-emitting layers of Example 3 were changed to the compounds and film thicknesses shown in Table 3.

[2145] Comparative Example 3

[2146] The organic EL element of Comparative Example 3 was fabricated in the same manner as Example 3, except that only the first light-emitting layer was formed as described in Table 3.

[2147] (Evaluation 2 of Organic EL Element)

[2148] For the organic EL elements obtained in Examples 3 to 4 and Comparative Example 3, a voltage was applied such that the current density reached 50 mA / cm 2 , and the time (LT95 (unit: hours)) until the luminance reached 95% of the initial luminance was measured. The results are shown in Table 3.

[2149] [Table 3]

[2150]

[2151] From the comparison between Example 4 and Comparative Example 3, which differ only in whether the host material in the first light-emitting layer has deuterium atoms in Table 3, it can be seen that the lifetime of the device in Example 4 is improved compared to that in Comparative Example 3.

[2152] <Fabrication of Organic EL Device 3>

[2153] Example 5

[2154] A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 1.1 mm, a length of 25 mm, and a width of 75 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then subjected to UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm.

[2155] The cleaned glass substrate with the transparent electrode was mounted on the substrate holder of a vacuum evaporation apparatus. First, on the surface where the transparent electrode was formed, Compound HI was evaporated to form a Compound HI film with a thickness of 5 nm so as to cover the transparent electrode. This HI film functions as a hole injection layer.

[2156] After forming this HI film, Compound HT was then evaporated to form an HT film with a thickness of 80 nm on the HI film. This HT film functions as the first hole transport layer.

[2157] After forming the HT film, Compound EBL-2 was then evaporated to form an EBL-2 film with a thickness of 10 nm on the HT film. This EBL-2 film functions as the second hole transport layer.

[2158] On the EBL-2 film, D-BH-1 (host material) and BD-1 (dopant material) were co-evaporated so that the ratio (mass ratio) of BD-1 reached 4% to form a first light-emitting layer with a thickness of 7.5 nm.

[2159] On the first light-emitting layer, BH-1 (host material) and BD-1 (dopant material) were co-evaporated so that the ratio (mass ratio) of BD-1 reached 4% to form a second light-emitting layer with a thickness of 17.5 nm.

[2160] On this second light-emitting layer, HBL-2 was evaporated to form an electron transport layer with a thickness of 10 nm. On this electron transport layer, ET as an electron injection material was evaporated to form an electron injection layer with a thickness of 15 nm. On this electron injection layer, LiF was evaporated to form a LiF film with a thickness of 1 nm. On this LiF film, metal Al was evaporated to form a metal cathode with a thickness of 80 nm.

[2161] The organic EL device was fabricated as described above. The layer structure of the device is as follows.

[2162] ITO (130 nm) / HI (5 nm) / HT (80 nm) / EBL-2 (10 nm) / D-BH-1:BD-1 (7.5 nm:4%) / BH-1:BD-1 (17.5 nm:4%) / HBL-2 (10 nm) / ET (15 nm) / LiF (1 nm) / Al (80 nm)

[2163] In the parentheses, the numbers expressed as percentages represent the ratio (mass %) of the dopant material in the light-emitting layer.

[2164] Examples 6 to 11 and Comparative Examples 4 to 5

[2165] An organic EL element was fabricated in the same manner as in Example 5, except that the compounds shown in Table 4 were used as the host material of the light-emitting layer and the film thickness of each light-emitting layer was the film thickness shown in Table 4.

[2166] (Evaluation 3 of organic EL element)

[2167] For the obtained organic EL element, a voltage was applied such that the current density reached 50 mA / cm 2 , and the time (LT90 (unit: hours)) until the luminance reached 90% of the initial luminance was measured. The LT90 value of the element of Comparative Example 4 having a single light-emitting layer containing a host material without deuterium atoms was set to 1, and the relative values of LT90 for the examples and comparative examples are shown in Table 4.

[2168] [Table 4]

[2169]

[2170] From the results in Table 4, it can be seen that for the elements of Examples 5 to 11 in which a first light-emitting layer containing a host material D-BH-1 having deuterium atoms and a second light-emitting layer containing a host material BH-1 without deuterium atoms are stacked in the light-emitting region, the lifetime is improved compared to the element of Comparative Example 4 having a single light-emitting layer containing a host material BH-1 without deuterium atoms.

[2171] Furthermore, it can also be seen that the elements of Examples 6 to 11 have the same lifetime as the element of Comparative Example 5 having a single light-emitting layer containing a host material D-BH-1 having deuterium atoms.

[2172] Example 12

[2173] An organic EL element was fabricated in the same manner as in Example 5, except that the host material of the first light-emitting layer was changed to D-BH-2, the host material of the second light-emitting layer was changed to BH-2, and the film thickness of each light-emitting layer was the film thickness shown in Table 5, and the evaluation was performed in the same manner as in Example 5. The results are shown in Table 5.

[2174] The layer structure of the element fabricated as described above is as follows.

[2175] ITO (130 nm) / HI (5 nm) / HT (80 nm) / EBL-2 (10 nm) / D-BH-2:BD-1 (2.5 nm: 4%) / BH-2:BD-1 (22.5 nm: 4%) / HBL-2 (10 nm) / ET (15 nm) / LiF (1 nm) / Al (80 nm)

[2176] In the parentheses, the numbers expressed as percentages represent the proportion (mass %) of the dopant material in the light-emitting layer.

[2177] Examples 13 to 20 and Comparative Examples 6 to 7

[2178] An organic EL element was fabricated in the same manner as in Example 12, except that the compound shown in Table 5 was used as the host material of the light-emitting layer and the film thickness of each light-emitting layer was the film thickness shown in Table 5, and the evaluation was performed in the same manner as in Example 5. The results are shown in Table 5.

[2179] [Table 5]

[2180]

[2181] From the results in Table 5, it can be seen that for the elements of Examples 12 to 20 in which the first light-emitting layer containing the host material D-BH-2 having deuterium atoms and the second light-emitting layer containing the host material BH-2 not having deuterium atoms are stacked in the light-emitting region, the lifetime is improved compared to the element of Comparative Example 6 having a single light-emitting layer containing the host material BH-2 not having deuterium atoms.

[2182] Furthermore, it can be seen that the elements of Examples 14 to 20 have the same lifetime as the element of Comparative Example 7 having a single light-emitting layer containing the host material D-BH-2 having deuterium atoms.

[2183] Example 21

[2184] An organic EL element was fabricated in the same manner as in Example 1, except that the dopant material of the first and second light-emitting layers was changed to BD-2, the proportion of BD-2 was changed to 2 mass %, and the film thickness of each light-emitting layer was the film thickness shown in Table 6, and the evaluation was performed in the same manner as in Example 5. The results are shown in Table 6.

[2185] The layer constitution of the device fabricated as described above is as follows.

[2186] ITO(130 nm) / HI(5 nm) / HT(80 nm) / EBL (10 nm) / D-BH-1:BD-2(5 nm:2%) / BH-1:BD-2(20 nm:2%) / HBL (10 nm) / ET(15 nm) / LiF(1 nm) / Al(80 nm)

[2187] The numbers in parentheses, expressed as percentages, represent the proportion (mass %) of the dopant material in the light-emitting layer.

[2188] Examples 22 to 28 and Comparative Example 8

[2189] An organic EL device was fabricated and evaluated in the same manner as in Example 21, except that the compounds shown in Table 6 were used as the host material of the light-emitting layer and the film thickness of each light-emitting layer was the film thickness shown in Table 6. The results are shown in Table 6.

[2190] [Table 6]

[2191]

[2192] From the results in Table 6, it can be seen that even when the dopant material of the light-emitting layer was changed to BD-2, the devices of Examples 21 to 28, in which the first light-emitting layer containing the host material D-BH-1 having deuterium atoms and the second light-emitting layer containing the host material BH-1 not having deuterium atoms were stacked, had an improved lifetime compared to the device of Comparative Example 8 having a single light-emitting layer containing the host material BH-1 not having deuterium atoms.

[2193] Example 29

[2194] An organic EL device was fabricated in the same manner as in Example 1, except that the dopant materials of the first and second light-emitting layers were changed to BD-3, the proportion of BD-3 was changed to 2 mass %, and the film thickness of each light-emitting layer was the film thickness shown in Table 7. Evaluation was carried out in the same manner as in Example 5. The results are shown in Table 7.

[2195] The layer constitution of the device fabricated as described above is as follows.

[2196] ITO(130 nm) / HI(5 nm) / HT(80 nm) / EBL (10 nm) / D-BH-1:BD-3(5 nm:2%) / BH-1:BD-3(20 nm:2%) / HBL (10 nm) / ET(15 nm) / LiF(1 nm) / Al(80 nm)

[2197] Inside the parentheses, the numbers expressed as percentages represent the proportion (mass %) of the dopant material in the light-emitting layer.

[2198] Examples 30 to 36 and Comparative Example 9

[2199] Except for using the compounds shown in Table 7 as the host materials of the light-emitting layers and making the film thicknesses of the respective light-emitting layers the film thicknesses shown in Table 7, an organic EL element was fabricated and evaluated in the same manner as in Example 29. The results are shown in Table 7.

[2200] [Table 7]

[2201]

[2202] From the results in Table 7, it can be seen that even when the dopant material of the light-emitting layer was changed to BD-3, the elements of Examples 29 to 36 in which the first light-emitting layer containing the host material D-BH-1 having deuterium atoms and the second light-emitting layer containing the host material BH-1 not having deuterium atoms were laminated had improved lifetimes compared to the element of Comparative Example 9 having a single light-emitting layer containing the host material BH-1 not having deuterium atoms.

[2203] Example 37

[2204] Except for changing the host material of the second light-emitting layer to BH-2 and making the film thicknesses of the first light-emitting layer and the second light-emitting layer 12.5 nm, respectively, an organic EL element was fabricated in the same manner as in Example 1 and evaluated in the same manner as in Example 5. The results are shown in Table 8.

[2205] The layer constitution of the element fabricated as described above is as follows.

[2206] ITO (130 nm) / HI (5 nm) / HT (80 nm) / EBL (10 nm) / D-BH-1:BD-1 (12.5 nm:4%) / BH-2:BD-1 (12.5 nm:4%) / HBL (10 nm) / ET (15 nm) / LiF (1 nm) / Al (80 nm)

[2207] Inside the parentheses, the numbers expressed as percentages represent the proportion (mass %) of the dopant material in the light-emitting layer.

[2208] Comparative Examples 10 to 11

[2209] Except for using the compounds shown in Table 8 as the host materials of the light-emitting layers, an organic EL element was fabricated and evaluated in the same manner as in Example 37. The results are shown in Table 8.

[2210] [Table 8]

[2211]

[2212] As can be seen from the results in Table 8, the element of Example 37, which includes the host material D-BH-1 having deuterium atoms in the first light-emitting layer and the host material BH-2 having a structure different from that of the host material D-BH-1 in the second light-emitting layer, has an improved lifetime compared to the element of Comparative Example 10, which includes the host material BH-1 without deuterium atoms in the first light-emitting layer and the host material BH-2 in the second light-emitting layer.

[2213] In addition, it can also be seen that the element of Example 37 has the same element lifetime as the element of Comparative Example 11, in which the first light-emitting layer and the second light-emitting layer respectively include the host materials D-BH-1 and D-BH-2 having deuterium atoms.

[2214] Example 38

[2215] An organic EL element was fabricated in the same manner as in Example 1, except that the host material of the first light-emitting layer was changed to D-BH-2 and the film thicknesses of the first light-emitting layer and the second light-emitting layer were 12.5 nm each, and the evaluation was performed in the same manner as in Example 5. The results are shown in Table 9.

[2216] The layer structure of the element fabricated as described above is as follows.

[2217] ITO(130 nm) / HI(5 nm) / HT(80 nm) / EBL (10 nm) / D-BH-2:BD-1(12.5 nm:4%) / BH-1:BD-1(12.5 nm:4%) / HBL (10 nm) / ET(15 nm) / LiF(1 nm) / Al(80 nm)

[2218] In the parentheses, the numbers represented as percentages indicate the proportion (mass %) of the dopant material in the light-emitting layer.

[2219] Comparative Examples 12 to 13

[2220] An organic EL element was fabricated and evaluated in the same manner as in Example 38, except that the compounds shown in Table 9 were used as the host materials of the light-emitting layer. The results are shown in Table 9.

[2221] [Table 9]

[2222]

[2223] As can be seen from the results in Table 9, the device of Example 38, which includes the host material D-BH-2 having deuterium atoms in the first light-emitting layer and the host material BH-1 having a structure different from that of the host material D-BH-2 in the second light-emitting layer, has an improved lifetime compared to the device of Comparative Example 12, which includes the host material BH-2 without deuterium atoms in the first light-emitting layer and the host material BH-1 in the second light-emitting layer.

[2224] Furthermore, it can also be seen that the device of Example 38 has the same device lifetime as the device of Comparative Example 13, in which the first light-emitting layer and the second light-emitting layer respectively include the host materials D-BH-2 and D-BH-1 having deuterium atoms.

[2225] Example 39

[2226] An organic EL device was fabricated in the same manner as in Example 5, except that the host material of the first light-emitting layer was changed to D-BH-4, the host material of the second light-emitting layer was changed to BH-2, and the film thicknesses of the first light-emitting layer and the second light-emitting layer were 12.5 nm, respectively, and evaluated in the same manner as in Example 5. The results are shown in Table 10.

[2227] The layer structure of the device fabricated as described above is as follows.

[2228] ITO (130 nm) / HI (5 nm) / HT (80 nm) / EBL-2 (10 nm) / D-BH-4:BD-1 (12.5 nm:4%) / BH-2:BD-1 (12.5 nm:4%) / HBL-2 (10 nm) / ET (15 nm) / LiF (1 nm) / Al (80 nm)

[2229] In the parentheses, the numbers expressed as percentages represent the proportion (mass%) of the dopant material in the light-emitting layer.

[2230] Examples 40 and Comparative Example 14

[2231] An organic EL device was fabricated and evaluated in the same manner as in Example 39, except that the compounds shown in Table 10 were used as the host materials of the light-emitting layer. The results are shown in Table 10.

[2232] [Table 10]

[2233]

[2234] As can be seen from the results in Table 10, the device of Example 39, which includes the host material D-BH-4 having deuterium atoms in the first light-emitting layer and the host material BH-2 having a structure different from that of the host material D-BH-4 in the second light-emitting layer, has an improved lifetime compared to the device of Comparative Example 14, which includes the host material BH-4 without deuterium atoms in the first light-emitting layer and the host material BH-2 in the second light-emitting layer.

[2235] Furthermore, it can also be seen that the device of Example 40, which includes the host material BH-4 without deuterium atoms in the first light-emitting layer and the host material D-BH-2 having deuterium atoms in the second light-emitting layer, has an improved lifetime compared to the device of Comparative Example 14.

[2236] Example 41

[2237] An organic EL device was fabricated in the same manner as in Example 5, except that the host material of the second light-emitting layer was changed to BH-4 and the film thicknesses of the first and second light-emitting layers were 12.5 nm each, and evaluated in the same manner as in Example 5. The results are shown in Table 11.

[2238] The layer structure of the device fabricated as described above is as follows.

[2239] ITO (130 nm) / HI (5 nm) / HT (80 nm) / EBL-2 (10 nm) / D-BH-1:BD-1 (12.5 nm:4%) / BH-4:BD-1 (12.5 nm:4%) / HBL-2 (10 nm) / ET (15 nm) / LiF (1 nm) / Al (80 nm)

[2240] In the parentheses, the numbers expressed as percentages represent the proportion (mass %) of the dopant material in the light-emitting layer.

[2241] Example 42 and Comparative Example 15

[2242] An organic EL device was fabricated and evaluated in the same manner as in Example 41, except that the compounds shown in Table 11 were used as the host materials of the light-emitting layer. The results are shown in Table 11.

[2243] [Table 11]

[2244]

[2245] As can be seen from the results in Table 11, the device of Example 41 in which the first light-emitting layer contains the host material D-BH-1 having deuterium atoms and the second light-emitting layer contains the host material BH-4 having a structure different from that of the host material D-BH-1 in the first light-emitting layer has an improved lifetime compared to the device of Comparative Example 15 in which the first light-emitting layer contains the host material BH-1 not having deuterium atoms and the second light-emitting layer contains the host material BH-4.

[2246] Furthermore, it can also be seen that the device of Example 42 in which the first light-emitting layer contains the host material BH-1 not having deuterium atoms and the second light-emitting layer contains the host material D-BH-4 having deuterium atoms has an improved lifetime compared to the device of Comparative Example 15.

[2247] Several embodiments and / or examples of the present invention have been described in detail above, but those skilled in the art can easily make many changes to these exemplary embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Therefore, these many changes are also included within the scope of the present invention.

[2248] All of the documents described in this specification and the contents of the application that is the basis of the Paris Convention priority of this application are incorporated by reference.

Claims

1. An organic electroluminescent element having: an anode, a cathode, and a light-emitting region located between the anode and the cathode; the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the first light-emitting layer and the second light-emitting layer are directly adjacent, the first light-emitting layer is located between the anode and the second light-emitting layer, each of the first light-emitting layer and the second light-emitting layer independently includes a host material and a dopant material, only one of the first light-emitting layer and the second light-emitting layer includes a compound having at least one deuterium atom as the host material, One of the first light-emitting layer and the second light-emitting layer contains a compound represented by the following formula (1A) or (1B) having at least one deuterium atom; the other contains a compound represented by the following formula (1A) or (1B) having no deuterium atom, wherein in the compound represented by the formula (1A) or (1B) having no deuterium atom, R 1 ~R 8 are all protium atoms, the host material having at least one deuterium atom is a compound represented by the following formula (1A) or (1B), in formula (1A), R 1 ~R 8 All are deuterium atoms; L 1A and L 2A each independently is: a single bond, an unsubstituted phenylene, an unsubstituted naphthylene, an unsubstituted biphenylene, an unsubstituted terphenyl, an unsubstituted anthracene, or an unsubstituted phenanthrene; Ar 1A and Ar 2A Each independently is: an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted terphenyl, an unsubstituted anthracenyl, or an unsubstituted phenanthryl; in formula (1B), R 1 ~R 8 All are deuterium atoms; L 1B and L 2B Each independently is: a single bond, or an unsubstituted arylene having 6 to 18 ring carbon atoms; Ar 2B is an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms; R 11B ~R 18B One of them is a single bond bonded to L 1B single bond; Not the single bond R bonded to L 1B ~R 11B ~R 18B Each independently is: a hydrogen atom; the ratio of the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having a deuterium atom, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) ≤ 0.9, R 1 ~R 8 When a hydrogen atom appears among the substituents other than those, the hydrogen atom may be a protium atom or a deuterium atom.

2. The organic electroluminescent element according to claim 1, wherein, relative to the entire light-emitting layer, the content of the host material in the light-emitting layer is 80% by mass or more and 99% by mass or less.

3. The organic electroluminescent element according to claim 1 or 2, wherein, relative to the entire light-emitting layer, the content of the dopant material in the light-emitting layer is 1% by mass or more and 20% by mass or less.

4. The organic electroluminescent element according to claim 1 or 2, wherein, the number of deuterium atoms of the compound having at least one deuterium atom is 1 to 100.

5. The organic electroluminescent element according to claim 1 or 2, wherein, the number of deuterium atoms of the compound having at least one deuterium atom is 1 to 80.

6. The organic electroluminescent element according to claim 1 or 2, wherein, when the compound having at least one deuterium atom is the host material, the number of deuterium atoms is 1 to 50.

7. The organic electroluminescent element according to claim 1 or 2, wherein, when the compound having at least one deuterium atom is the host material, the number of deuterium atoms is 1 to 40.

8. The organic electroluminescent element according to claim 1 or 2, wherein, Selected from L that is not a single bond 1A and L that is not a single bond 2A Ar 1A and Ar 2A At least one hydrogen atom in one or more groups is a deuterium atom, or selected from L that is not a single bond 1B and L that is not a single bond 2B Ar 2B and R that is not a single bond bonded to L 1B ~R 11B ~R 18B At least one hydrogen atom in one or more groups is a deuterium atom.

9. The organic electroluminescent element according to claim 1 or 2, wherein, in the light-emitting layer, relative to the total of the compound represented by the formula (1A) or (1B) and the compound having the same structure as the compound represented by the formula (1A) or (1B) except that it contains only protium atoms as hydrogen atoms, the content ratio of the latter is 99 mol% or less.

10. The organic electroluminescent element according to claim 1 or 2, in formula (1A), L 1A and L 2A each independently is: a single bond, an unsubstituted phenylene, an unsubstituted naphthylene, or Unsubstituted biphenylene group; Ar 1A and Ar 2A Each independently is: Unsubstituted phenyl group, Unsubstituted naphthyl group, or Unsubstituted biphenyl group.

11. The organic electroluminescent element according to claim 1 or 2, wherein, At least one of the hydrogen atoms possessed by one or more selected from L in the formula (1A) 1A and L 2A is a deuterium atom.

12. The organic electroluminescent element according to claim 1 or 2, wherein, One or more selected from L in the formula (1A) 1A and L 2A are: An unsubstituted phenylene group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted naphthylene group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted biphenylene group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted terphenylene group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted anthrylene group in which at least one of the hydrogen atoms is a deuterium atom, or An unsubstituted phenanthrylene group in which at least one of the hydrogen atoms is a deuterium atom.

13. The organic electroluminescent element according to claim 1 or 2, wherein, L in the formula (1A) above 1A and L 2A each independently represents a single bond, an unsubstituted phenylene group, or a naphthylene group.

14. The organic electroluminescent element according to claim 1 or 2, wherein, L in the formula (1A) 1A and L 2A at least one of them is a single bond.

15. The organic electroluminescent element according to claim 1 or 2, wherein, At least one of the hydrogen atoms possessed by one or more selected from Ar in the formula (1A) 1A and Ar 2A is a deuterium atom.

16. The organic electroluminescent element according to claim 1 or 2, wherein, One or more selected from Ar in the formula (1A) 1A and Ar 2A is as follows: An unsubstituted phenyl group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted naphthyl group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted biphenyl group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted terphenyl group in which at least one of the hydrogen atoms is a deuterium atom, An unsubstituted anthryl group in which at least one of the hydrogen atoms is a deuterium atom, or An unsubstituted phenanthryl group in which at least one of the hydrogen atoms is a deuterium atom.

17. The organic electroluminescent element according to claim 1 or 2, wherein, Ar in the formula (1A) above 1A and Ar 2A are each independently an unsubstituted phenyl group, an unsubstituted naphthyl group, or an unsubstituted phenanthryl group.

18. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by the formula (1A) is one or more selected from the following group:

19. In the formula (1B) of the organic electroluminescent element according to claim 1 or 2, L 1B and L 2B are each independently a single bond; Ar 2B is an unsubstituted aryl group having 6 to 18 ring carbon atoms; R 11B ~R 18B One of them is a single bond bonded to L 1B single bond; Not the single bond R bonded to L 1B to R of the single bond bonded to the L 11B ~R 18B Each independently represents a hydrogen atom.

20. The organic electroluminescent element according to claim 1 or 2, wherein, At least one of the hydrogen atoms possessed by one or more selected from L in the formula (1B) 1B and L 2B is a deuterium atom.

21. The organic electroluminescent element according to claim 1 or 2, wherein, One or more selected from L in the formula (1B) 1B and L 2B are: an unsubstituted arylene group having 6 to 18 ring-forming carbon atoms in which at least one of the hydrogen atoms is a deuterium atom.

22. The organic electroluminescent element according to claim 1 or 2, wherein, L in the formula (1B) described above 1B and L 2B each independently represents a single bond or an unsubstituted arylene group having 6 to 14 ring carbon atoms.

23. The organic electroluminescent element according to claim 1 or 2, wherein, L in the formula (1B) 1B and L 2B at least one of them is a single bond.

24. The organic electroluminescent element according to claim 1 or 2, wherein, R in the formula (1B) 11B ~R 18B At least one of those that are not single bonds bonded to L 1B is a deuterium atom.

25. The organic electroluminescent element according to claim 1 or 2, wherein, Ar in the formula (1B) 2B At least one of the hydrogen atoms it has is a deuterium atom.

26. The organic electroluminescent element according to claim 1 or 2, wherein, Ar in the formula (1B) 2B is an unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, at least one of which is a deuterium atom instead of a hydrogen atom.

27. The organic electroluminescent element according to claim 1 or 2, wherein, Ar in the formula (1B) 2B is selected from the groups represented by the following formulae (a1B) to (a4B), In formulas (a1B) to (a4B), * is a single bond bonded to L 2B ; R 21B is: Unsubstituted alkyl group having 1 to 50 carbon atoms; m1B is 0; m2B is 0; m3B is 0.

28. The organic electroluminescent element according to claim 1 or 2, wherein, L in the formula (1B) 1B and L 2B are each independently a single bond.

29. The organic electroluminescent element according to claim 1 or 2, wherein, The compound represented by the formula (1B) is one or more selected from the following group: [Chemical formula 27] [Chemical formula 28] [Chemical formula 31] [Chemical formula 32] [Chemical formula 35] [Chemical formula 36] [Chemical formula 39] [Chemical formula 40] [Chemical formula 41] [Chemical formula 42] [Chemical formula 43] [Chemical formula 44] [Chemical formula 45] 30. The organic electroluminescent element according to claim 1 or 2, wherein, The host material having at least 1 deuterium atom is the compound represented by the formula (1A), L 1A is a single bond, Ar 1A is an unsubstituted phenyl group, an unsubstituted biphenyl group or an unsubstituted naphthyl group.

31. The organic electroluminescent element according to claim 1 or 2, wherein, The host material having at least one deuterium atom is the compound represented by the formula (1A), L 1A is an unsubstituted phenylene or an unsubstituted naphthylene, Ar 1A is an unsubstituted phenyl or an unsubstituted naphthyl.

32. The organic electroluminescent element according to claim 1 or 2, wherein, the compound having a deuterium atom represented by the formula (1A) or formula (1B) contained in any one of the first light-emitting layer and the second light-emitting layer is selected from the following group, 33. The organic electroluminescent element according to claim 1 or 2, wherein, the compound having a deuterium atom represented by the formula (1A) or formula (1B) contained in the first light-emitting layer is one or more selected from the following group, 34. The organic electroluminescent element according to claim 1 or 2, wherein, the first light-emitting layer contains a compound having at least one deuterium atom.

35. The organic electroluminescent element according to claim 1 or 2, wherein, the first light-emitting layer contains only a compound having at least one deuterium atom as a host material.

36. The organic electroluminescent element according to claim 1 or 2, wherein, the compound having at least one deuterium atom is one or both of a host material and a dopant material.

37. The organic electroluminescent element according to claim 1 or 2, wherein, the first light-emitting layer contains a compound having at least one deuterium atom, the second light-emitting layer contains a compound having an anthracene skeleton without a deuterium atom.

38. The organic electroluminescent element according to claim 34, wherein, when the deuterium atom of the host material of the first light-emitting layer is replaced with a protium atom, the chemical structure is the same as that of the host material of the second light-emitting layer.

39. The organic electroluminescent element according to claim 1 or 2, wherein, the dopant material of the first light-emitting layer is the same as the dopant material of the second light-emitting layer.

40. The organic electroluminescent element according to claim 1 or 2, wherein, the compound having an anthracene skeleton without a deuterium atom is one or more selected from the following group, 41. The organic electroluminescent element according to claim 40, wherein, the compound having an anthracene skeleton without a deuterium atom contained in the second light-emitting layer is one or more selected from the following group, 42. The organic electroluminescent element according to claim 1 or 2, wherein, at least one of the first light-emitting layer and the second light-emitting layer is a light-emitting layer containing one or two or more host materials.

43. The organic electroluminescent element according to claim 1 or 2, wherein, at least one of the first light-emitting layer and the second light-emitting layer is a light-emitting layer containing two or more host materials.

44. The organic electroluminescent element according to claim 43, wherein, when the light-emitting layer containing two or more host materials contains a host material containing a deuterium atom, only one of them is a compound having a deuterium atom, and the other is a compound without a deuterium atom.

45. The organic electroluminescent element according to claim 43, wherein, when the light-emitting layer containing two or more host materials contains a host material containing a deuterium atom, all of them are compounds having a deuterium atom.

46. The organic electroluminescent element according to claim 1 or 2, Among them, the first light-emitting layer does not contain a metal complex.

47. The organic electroluminescent element according to claim 1 or 2, wherein, the second light-emitting layer does not contain a metal complex.

48. The organic electroluminescent element according to claim 1 or 2, wherein, the first light-emitting layer does not contain a phosphorescent metal complex.

49. The organic electroluminescent element according to claim 1 or 2, wherein, the second light-emitting layer does not contain a phosphorescent metal complex.

50. The organic electroluminescent element according to claim 1 or 2, wherein, the first light-emitting layer does not contain an iridium complex.

51. The organic electroluminescent element according to claim 1 or 2, wherein, the second light-emitting layer does not contain an iridium complex.

52. The organic electroluminescent element according to claim 1 or 2, wherein, the first light-emitting layer does not contain a phosphorescent dopant material.

53. The organic electroluminescent element according to claim 1 or 2, wherein, the second light-emitting layer does not contain a phosphorescent dopant material.

54. The organic electroluminescent element according to claim 1 or 2, wherein, the first light-emitting layer is a light-emitting layer that emits fluorescence.

55. The organic electroluminescent element according to claim 1 or 2, wherein, the second light-emitting layer is a light-emitting layer that emits fluorescence.

56. The organic electroluminescent element according to claim 1 or 2, wherein, one of the first light-emitting layer and the second light-emitting layer contains a compound containing deuterium atoms in an amount exceeding 0.015%.

57. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the light-emitting layer containing the compound having deuterium atoms, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having deuterium atoms, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) < 0.

9.

58. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the light-emitting layer containing the compound having deuterium atoms, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having deuterium atoms, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) < 0.

7.

59. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the light-emitting layer containing the compound having deuterium atoms, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having deuterium atoms, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) < 0.

6.

60. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the light-emitting layer containing the compound having deuterium atoms, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having deuterium atoms, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) < 0.

5.

61. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the light-emitting layer containing the compound having deuterium atoms, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having deuterium atoms, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) < 0.

4.

62. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having a deuterium atom, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) ≤ 0.

7.

63. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, to the film thickness of the light-emitting layer not containing the compound having a deuterium atom, i.e., film thickness T2, is 0.3 < (T1 / (T1 + T2)) ≤ 0.

5.

64. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the first light-emitting layer, i.e., film thickness T1, to the film thickness of the second light-emitting layer, i.e., film thickness T2, is 0.05 < (T1 / (T1 + T2)) < 0.

9.

65. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the first light-emitting layer, i.e., film thickness T1, to the film thickness of the second light-emitting layer, i.e., film thickness T2, is 0.05 < (T1 / (T1 + T2)) < 0.

6.

66. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the first light-emitting layer, i.e., film thickness T1, to the film thickness of the second light-emitting layer, i.e., film thickness T2, is 0.1 < (T1 / (T1 + T2)) < 0.

5.

67. The organic electroluminescent element according to claim 1 or 2, wherein, the ratio of the film thickness of the first light-emitting layer, i.e., film thickness T1, to the film thickness of the second light-emitting layer, i.e., film thickness T2, is 0.1 < (T1 / (T1 + T2)) < 0.

4.

68. The organic electroluminescent element according to claim 1 or 2, wherein, the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, is 2.5 nm or more.

69. The organic electroluminescent element according to claim 1 or 2, wherein, the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, is 7.5 nm or more.

70. The organic electroluminescent element according to claim 1 or 2, wherein, the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, is 22.5 nm or less.

71. The organic electroluminescent element according to claim 1 or 2, wherein, the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, is 17.5 nm or less.

72. The organic electroluminescent element according to claim 1 or 2, wherein, the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, is 12.5 nm or less.

73. The organic electroluminescent element according to claim 1 or 2, wherein, the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, is 10 nm or less.

74. The organic electroluminescent element according to claim 1 or 2, wherein, the film thickness of the light-emitting layer containing the compound having a deuterium atom, i.e., film thickness T1, is 5 nm or more and 17.5 nm or less.

75. The organic electroluminescent element according to claim 1 or 2, wherein, The film thickness of the light-emitting layer containing the compound having deuterium atoms, i.e., the film thickness T1, is 5 nm or more and 12.5 nm or less.

76. The organic electroluminescent element according to claim 1 or 2, wherein, the dopant material is selected from the compounds represented by the following formulas (17), (33), and (43), In formula (17), R 111 ~R 118 Two or more adjacent groups of two or more of them are not bonded to each other to form an unsubstituted saturated or unsaturated ring; R 111 ~R 118 Each independently represents a hydrogen atom; R 121 ~R 127 Among them, two or more adjacent groups do not form an unsubstituted saturated or unsaturated ring by bonding to each other; R 121 ~R 127 Each independently is: a hydrogen atom, or an unsubstituted alkyl group having 1 to 50 carbon atoms; R 131 ~R 135 Each independently is: a hydrogen atom, or an unsubstituted alkyl group having 1 to 50 carbon atoms; In formula (33), R 351 and R 352 each independently represents a hydrogen atom; R 361 ~R 364 Each independently is: an aryl group having 6 to 50 ring-constituting carbon atoms substituted with an alkyl group having 1 to 50 carbon atoms or an unsubstituted aryl group having 6 to 50 ring-constituting carbon atoms; In formula (43), R 431 Bonding with R 446 does not form an unsubstituted heterocycle; R 433 Bonding with R 447 does not form an unsubstituted heterocycle; R 434 Bonding with R 451 does not form an unsubstituted heterocycle; R 441 Bonding with R 442 does not form an unsubstituted heterocycle; R 431 ~R 451 Two or more than two adjacent groups among them are not bonded to each other to form an unsubstituted saturated or unsaturated ring; R 431 ~R 451 Each independently is: a hydrogen atom, or an unsubstituted alkyl group having 1 to 50 carbon atoms.

77. The organic electroluminescent element according to claim 76, wherein, the compound represented by formula (17) is one or more selected from the following group, 78. The organic electroluminescent element according to claim 76, wherein, the compound represented by formula (33) is one or more selected from the following group, 79. The organic electroluminescent element according to claim 76, wherein, the compound represented by formula (43) is the compound represented by the following formula (43A), In formula (43A), R 461 is: a hydrogen atom, or an unsubstituted alkyl group having 1 to 50 carbon atoms; R 462 ~R 465 Each independently is: an unsubstituted alkyl group having 1 to 50 carbon atoms.

80. The organic electroluminescent element according to claim 76, wherein, the compound represented by formula (43) is one or more selected from the following group, 81. The organic electroluminescent element according to claim 1 or 2, wherein, the dopant material is a blue light-emitting dopant.

82. The organic electroluminescent element according to claim 1 or 2, wherein, the dopant material is one or more selected from the following group, 83. The organic electroluminescent element according to claim 76, wherein, the first light-emitting layer contains the compound represented by formula (1A) or (1B), the second light-emitting layer contains a compound having the same chemical structure as when all deuterium atoms of the compound represented by formula (1A) or (1B) are replaced with protium atoms, the dopant material is a compound selected from the compounds represented by any one of formulas (17), (33), and (43).

84. The organic electroluminescent element according to claim 83, wherein, the host material contained in the first light-emitting layer, the host material contained in the second light-emitting layer, and the dopant material are each one or more selected from the following group, Host material contained in the first light-emitting layer: Host material contained in the second light-emitting layer: Dopant material:

85. The organic electroluminescent element according to claim 1 or 2, wherein, the light-emitting region further has a third light-emitting layer, the second light-emitting layer is directly adjacent to the third light-emitting layer, the third light-emitting layer is located between the cathode and the second light-emitting layer.

86. The organic electroluminescent element according to claim 1 or 2, wherein, the light-emitting region further has a third light-emitting layer, The second light-emitting layer is directly adjacent to the third light-emitting layer. The third light-emitting layer is located between the cathode and the second light-emitting layer. The second light-emitting layer contains a compound having at least one deuterium atom.

87. The organic electroluminescent element according to claim 1 or 2, wherein, a third light-emitting layer and a fourth light-emitting layer are further provided between the second light-emitting layer and the cathode, the third light-emitting layer is directly adjacent to the fourth light-emitting layer, the fourth light-emitting layer is provided between the third light-emitting layer and the cathode, either the third light-emitting layer or the fourth light-emitting layer contains a compound having at least one deuterium atom.

88. The organic electroluminescent element according to claim 1 or 2, wherein, a third light-emitting layer and a fourth light-emitting layer are further provided, the third light-emitting layer is directly adjacent to the fourth light-emitting layer, the fourth light-emitting layer is provided between the third light-emitting layer and the cathode, either the third light-emitting layer or the fourth light-emitting layer contains a compound having at least one deuterium atom, a charge generation layer is provided between the second light-emitting layer and the third light-emitting layer.

89. The organic electroluminescent element according to claim 87, which has a tandem structure in which a light-emitting layer having two stacked structures is provided.

90. The organic electroluminescent element according to claim 87, which is a white light-emitting element.

91. An electronic device, which has the organic electroluminescent element according to any one of claims 1 to 90.

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